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1. 发明授权

US07446186B2 Pyrroles substituted by oligonucleotides 失效
标题翻译：由寡核苷酸取代的吡咯
公开(公告)号：US07446186B2
公开(公告)日：2008-11-04
申请号：US10536317
申请日：2003-12-16
申请人： Bernard Mandrand , Daniela Zsoldos , Alain Laurent , Carole Chaix , Nicolas Spinelli
发明人： Bernard Mandrand , Daniela Zsoldos , Alain Laurent , Carole Chaix , Nicolas Spinelli
IPC分类号： C07H21/00 , C12Q1/68
CPC分类号： C07H21/00 , Y02P20/55
摘要： The invention relates to novel pyrrole derivatives of the formula (I) which make it possible to immobilize and address oligonucleotides by electropolymerization. Said invention also relates to thus produced electroactive polymers and to methods for using them for detecting, identifying and dosing analytes in a sample. (I) wherein R1 is one type of oligonucleotide, Y is S or O, X is a spacer arm selected from —(CH2)—O—, —(CH2) P O—[(CH2)2—O]q—, —(CH2)r; —CO—NR′—(CH2)r—O—, —CH2r—NCH3—(CH2)r—O—, —CH2)rCO—NR′—[CH2)2—O]s—, —(CH2)rNCH3[(CH2)2—O] S —, R′ is H or CH3, n is an integer number ranging from 1 to 5, p is an integer number ranging from 1 to 2, q is an integer number ranging from 1 to 4, r is an integer number ranging from 1 to 3, r′ is an integer number ranging from 1 to 3, s is an integer number ranging from 1 to 3, n, p, q, r, r′ and s are identical or different, a pyrrole cycle is substituted in a position 2, 3, 4 or 5.
摘要翻译：本发明涉及式（I）的新型吡咯衍生物，其可以通过电聚合固定和解决寡核苷酸。所述发明还涉及如此制备的电活性聚合物以及使用它们用于检测，鉴定和给药样品中分析物的方法。（I）其中R 1是一种类型的寡核苷酸，Y是S或O，X是选自以下的间隔臂 - （CH 2）2 - ， - （ CH 2 O - [（CH 2）2 -O] q - ， - （CH 2）n - -CO-NR' - （CH 2）2 -O - ， - CH 2 R n -NCH 3 - （CH 2）n -O - ， - CH 2）n CO-NR' - [CH 2 - 2 - > - - - - - - - - - - - - - - - - （CH 2） [（CH 2）2 -O] -SS - ，R'是H或CH 3， 3 ，n为1〜5的整数，p为1〜2的整数，q为1〜4的整数，r为1〜3的整数， r'为1〜3的整数，s为1〜3的整数，n，p，q，r，r'和s相同或不同，吡咯环在2位， 3，4或5。

2. 发明授权

US07301041B2 Bi-functional metallocenes, preparation process and use in the labeling or biological molecules 失效
公开(公告)号：US07301041B2
公开(公告)日：2007-11-27
申请号：US10501347
申请日：2003-02-14
申请人： Carole Chaix-Bauvais , Corinne Moustrou , Aude-Emmanuelle Navarro , Hugues Brisset , Francis Garnier , Bernard Mandrand , Nicolas Spinelli
发明人： Carole Chaix-Bauvais , Corinne Moustrou , Aude-Emmanuelle Navarro , Hugues Brisset , Francis Garnier , Bernard Mandrand , Nicolas Spinelli
IPC分类号： C07F17/02 , C07K1/00
CPC分类号： C07F17/02 , Y02P20/55
摘要： The invention relates to bi-functionalised metallocenes of general formula (I) where Me=a transition metal, preferably chosen from Fe, Ru and Os, Y and Z, when identical are selected from —(CH2)n—O—, (CH2)—O—[(CH2)2—O]P— and —(CH2)q—CONH—(CH2)r—O—, or Y=—(CH2)S—NH— and Z=—(CH2)t—COO—, n=a whole number from 3 to 6 inclusive, p=a whole number from 1 to 4 inclusive, q=a whole number from 0 to 2 inclusive, r=a whole number from 0 to 2 inclusive, s=a whole number from 2 to 5 inclusive, t=a whole number from 3 to 6 inclusive, R and R′=H atoms or are protective groups used in oligonucleotide and peptide synthesis, where at least one of R or R′ is protective group used in oligonucleotide and peptide synthesis and R and R′ are as defined below: (i) when Z and Y are selected from (CH2)n—O—, —(CH2)—O—[(CH2)2—O]p— and —(CH2)q—CONH—(CH2)r—O—, then R and R′ are protective groups used in oligonucleotide synthesis and R is a group which can leave a free OH group after deprotection, preferably a photolabile group such as monomethroxythoxytrityl, dimethoxytrityl, t-butyldimethylsilyl, acetyl or trifluroacetyl, and R′ is a phosphorylated group which can react with a free OH, preferably a phosphodiester, phosphoramidite or H-phosphonate and (ii) when Y=—(CH2)s—NH— and Z=—(CH2)t—COO—, then R is a protective group used in the synthesis of peptides and is an amino-protecting group, preferably 9-fluorenyloxycarbonyl, t-butoxycarbonyl or benzyloxycarbonyl and R′=H. The above is applied in marking.

3. 发明申请

US20050038234A1 Bi-functionalised metallocenes use for marking biological molecules 失效
标题翻译：双功能金属茂用于标记生物分子
公开(公告)号：US20050038234A1
公开(公告)日：2005-02-17
申请号：US10501347
申请日：2003-02-14
申请人： Carole Chaix-Bauvais , Corinne Moustrou , Aude-Emmanuelle Navarro , Hugues Brisset , Francis Garnier , Bernard Mandrand , Nicolas Spinelli
发明人： Carole Chaix-Bauvais , Corinne Moustrou , Aude-Emmanuelle Navarro , Hugues Brisset , Francis Garnier , Bernard Mandrand , Nicolas Spinelli
IPC分类号： C12N15/00 , A61K49/00 , C07F17/00 , C07F17/02 , C07H21/04 , C07K5/00 , C07K7/00 , C07K14/00 , C07K1/00
CPC分类号： C07F17/02 , Y02P20/55
摘要： The invention relates to bi-functionalised metallocenes of general formula (I) where Me=a transition metal, preferably chosen from Fe, Ru and Os, Y and Z, when identical are selected from —(CH2)n—O—, (CH2)—O—[(CH2)2—O]P— and —(CH2)q—CONH—(CH2)r—O—, or Y=—(CH2)S—NH— and Z=—(CH2)t—COO—, n=a whole number from 3 to 6 inclusive, p=a whole number from 1 to 4 inclusive, q=a whole number from 0 to 2 inclusive, r=a whole number from 0 to 2 inclusive, s=a whole number from 2 to 5 inclusive, t=a whole number from 3 to 6 inclusive, R and R′=H atoms or are protective groups used in oligonucleotide and peptide synthesis, where at least one of R or R′ is protective group used in oligonucleotide and peptide synthesis and R and R′ are as defined below: (i) when Z and Y are selected from (CH2)n—O—, —(CH2)—O—[(CH2)2—O]p— and —(CH2)q—CONH—(CH2)r—O—, then R and R′ are protective groups used in oligonucleotide synthesis and R is a group which can leave a free OH group after deprotection, preferably a photolabile group such as monomethroxythoxytrityl, dimethoxytrityl, t-butyldimethylsilyl, acetyl or trifluroacetyl, and R′ is a phosphorylated group which can react with a free OH, preferably a phosphodiester, phosphoramidite or H-phosphonate and (ii) when Y=—(CH2)n—NH— and Z=—(CH2)t—COO—, then R is a protective group used in the synthesis of peptides and is an amino-protecting group, preferably 9-fluorenyloxycarbonyl, t-butoxycarbonyl or benzyloxycarbonyl and R′=H. The above is applied in marking.
摘要翻译：本发明涉及通式（I）的双官能化金属茂，其中Me =过渡金属，优选选自Fe，Ru和Os，Y和Z，当相同时，选自 - （CH 2）n O-，（CH 2） O - [（CH 2）2 -O] P - 和 - （CH 2）q -CONH-（CH 2）r O-或Y = - （CH 2）S -NH-和Z = - （CH 2）t -COO-， n =从3到6的整数，p =从1到4的整数，q =从0到2的整数，包括0和2，r =从0到2的整数，s =从 2〜5，t = 3〜6的整数，R和R'= H原子，或者是寡核苷酸和肽合成中使用的保护基，其中R或R'中的至少一个为寡核苷酸中使用的保护基，肽合成和R和R'定义如下：（i）当Z和Y选自（CH 2）n O-， - （CH 2）-O - [（CH 2）2 -O] p - 和 - （CH 2） q-CONH-（CH 2）r O - ，则R和R'是寡核苷酸合成中使用的保护基，R是在去保护后可以留下游离OH基团的基团，顺式基团如单甲氧基三苯甲基，二甲氧基三苯甲基，叔丁基二甲基甲硅烷基，乙酰基或三氟乙酰基，R'是可以与游离OH，优选磷酸二酯，亚磷酰胺或H-膦酸酯反应的磷酸化基团，和（ii）当Y = - （CH2 ）n-NH-和Z = - （CH2）t-COO-，则R是用于合成肽的保护基，并且是氨基保护基，优选9-氟芳氧基羰基，叔丁氧基羰基或苄氧基羰基和R' = H。上述适用于标记。

4. 发明申请

US20060189555A1 Pyrroles substituted by oligonucleotides 失效
标题翻译：由寡核苷酸取代的吡咯
公开(公告)号：US20060189555A1
公开(公告)日：2006-08-24
申请号：US10536317
申请日：2003-12-16
申请人： Bernard Mandrand , Daniela Zsoldos , Alain Laurent , Carole Chaix , Nicolas Spinelli
发明人： Bernard Mandrand , Daniela Zsoldos , Alain Laurent , Carole Chaix , Nicolas Spinelli
IPC分类号： A61K48/00 , A61K31/7056 , C07H21/02 , C07H19/04
CPC分类号： C07H21/00 , Y02P20/55
摘要： The invention relates to novel pyrrole derivatives of the formula (I) which make it possible to immobilize and address oligonucleotides by electropolymerization. Said invention also relates to thus produced electroactive polymers and to methods for using them for detecting, identifying and dosing analytes in a sampe. (I) wherein R1 is one type of oligonucleotide, Y is S or O, X is a spacer arm selected from —(CH2)—O—, —(CH2) P O—[(CH2)2—O]q—, —(CH2)r; —CO—NR—(CH2)r-0-, —CH2r—NCH3—(CH2)r—O—, —CH2)rCO—NR′—[CH2)2—O]s—, —(CH2)rNCH3[(CH2)2—O] S —, R′ is H or CH3, n is an integer number ranging from 1 to 5, p is an integer number ranging from 1 to 2, q is an integer number ranging from 1 to 4, r is an integer number ranging from 1 to 3, r′ is an integer number ranging from 1 to 3, s is an integer number ranging from 1 to 3, n, p, q, r, r′ and s are identical or different, a pyrrole cycle is substituted in a position 2, 3, 4 or 5.
摘要翻译：本发明涉及式（I）的新型吡咯衍生物，其可以通过电聚合固定和解决寡核苷酸。所述发明还涉及由此产生的电活性聚合物及其用于检测，鉴定和给予分析物的方法。（I）其中R 1是一种类型的寡核苷酸，Y是S或O，X是选自以下的间隔臂 - （CH 2）2 - ， - （ CH 2 O - [（CH 2）2 -O] q > - ， - （CH 2）r < -CO-NR-（CH 2）r -O - ， - CH 2 R n -NCH 3 - （CH 2） -O - ， - CH 2）NR CO - NR' - [CH 2 N 2） 2 - - - - - - - - - - - - - - - - - - - （CH 2） [（CH 2）2 -O] -S SB， - R'是H或CH 3，n是 1〜5的整数，p为1〜2的整数，q为1〜4的整数，r为1〜3的整数，r'为从 1至3，s为1至3的整数，n，p，q，r，r'和s相同或不同，在2,3,4或5位置上取代吡咯环。

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