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11. 发明授权

US06414122B1 Bifunctional boronic compound complexing reagents and complexes 失效
标题翻译：双功能硼酸化合物络合物络合物
公开(公告)号：US06414122B1
公开(公告)日：2002-07-02
申请号：US09651007
申请日：2000-08-29
申请人： Clarence N. Ahlem , Robert J. Kaiser , Kevin P. Lund , Mark L. Stolowitz
发明人： Clarence N. Ahlem , Robert J. Kaiser , Kevin P. Lund , Mark L. Stolowitz
IPC分类号： C07F504
CPC分类号： C07C233/49 , C07C229/38 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , G01N33/54353 , Y10S530/81 , Y10S530/816
摘要： Embodiments include reagents to modify a bioactive species for incorporating a bifunctional boronic compound complexing moiety for subsequent conjugation to a different or same bioactive species having pendant phenylboronic acid moieties of General Formula I, wherein group R is an electrophilic or nucleophilic moiety suitable for reaction of the putative bifunctional boronic compound complexing reagent with a bioactive species, wherein group R2 is selected from one of H and OH moieties, and wherein group R3 is selected from one of an alkyl and a methylene bearing an electronegative substituent. Group Z is a spacer selected from (CH2)n and CH2O(CH2CH2O)n2, wherein n is an integer of from 1 to 5, and wherein n2 is an integer of from 1 to 4. Group Z2 and Z3 is a spacer and need not be the same.
摘要翻译：实施方案包括用于修饰生物活性物质以用于掺入双功能硼化合物络合部分以用于随后与不同或相同的具有通式I的苯基硼酸部分的生物活性物质结合的试剂，其中基团R是适于反应的亲电子或亲核部分其中基团R2选自H和OH部分之一，其中基团R3选自具有电负性取代基的烷基和亚甲基之一。 Z为选自（CH 2）n和CH 2 O（CH 2 CH 2 O）n 2的间隔基，其中n为1〜5的整数，n2为1〜4的整数.Z2和Z3为间隔基，不一样

12. 发明授权

US5872224A Boronic compound complexing reagents and highly stable complexes 失效
标题翻译：硼化合物络合剂和高度稳定的络合物
公开(公告)号：US5872224A
公开(公告)日：1999-02-16
申请号：US956194
申请日：1997-10-22
申请人： Mark L. Stolowitz , Robert J. Kaiser , Kevin P. Lund
发明人： Mark L. Stolowitz , Robert J. Kaiser , Kevin P. Lund
IPC分类号： C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/44 , C07D207/452 , C07D207/46 , C07D213/71 , C07F5/02 , C07F5/04 , C07K5/02 , G01N33/543
CPC分类号： C07C233/51 , C07C229/38 , C07C233/49 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/452 , C07D207/46 , C07D213/71 , C07F5/025 , C07K5/0207 , G01N33/54353
摘要： Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIV, and General Formula CVI. In one embodiment, the reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one of intermediate amide and disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.3 is selected from one of an H, an alkyl, and a methylene or ethylene moiety with an electronegative substituent; and BAS and BAS* are biologically active species.
摘要翻译：硼化合物络合剂，硼化合物络合物，以及合成这些试剂和络合物的方法。这些试剂和络合物包括通式CIV和通式CVI所示的那些。在一个实施方案中，通式CIV的试剂可用于与硼化合物形成络合物，例如通式CVI所示的络合物。通式CVI在一个实施方案中，组Z包含长度为至多约6碳当量的饱和或不饱和链的间隔基，约6至18的无支链饱和或不饱和链中间体酰胺和二硫化物部分中的至少一个长度的碳当量和长度为约3至12碳当量的聚乙二醇链; 基团R3选自具有电负性取代基的H，烷基和亚甲基或亚乙基部分中的一个; BAS和BAS *是生物活性物种。

13. 发明授权

US5869623A Boronic compound complexing reagents and complexes 失效
标题翻译：硼化合物络合剂和配合物
公开(公告)号：US5869623A
公开(公告)日：1999-02-09
申请号：US956204
申请日：1997-10-22
申请人： Mark L. Stolowitz , Robert J. Kaiser , Kevin P. Lund , Steven M. Torkelson
发明人： Mark L. Stolowitz , Robert J. Kaiser , Kevin P. Lund , Steven M. Torkelson
IPC分类号： C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/44 , C07D207/452 , C07D207/46 , C07D213/71 , C07F5/02 , C07F5/04 , C07K5/02 , G01N33/543
CPC分类号： C07D207/452 , C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/46 , C07D213/71 , C07F5/025 , C07K5/0207 , G01N33/54353
摘要： Boron compound complexing reagents, intermediate reagents of those reagents, and methods of synthesizing these reagents are disclosed. These reagents, including those shown as General Formula II may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain from about 6 to 18 carbon equivalents in length with at least one intermediate amide or disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.2 is one of an alkyl and a methylene group with an electronegative moiety; and BAS is a biologically active species.
摘要翻译：公开了硼化合物络合试剂，那些试剂的中间试剂和合成这些试剂的方法。在本文所述的进一步反应后，可以使用这些试剂，包括通式II所示的试剂，与硼酸化合物如苯基硼酸或其衍生物复合。通式II在一个实施方案中，基团Z包括长度为至多约6碳当量的饱和或不饱和链的间隔基，至少约6至18个碳当量长度的无支链饱和或不饱和链一个中间体酰胺或二硫化物部分，和长度为约3至12个碳当量的聚乙二醇链; 基团R2是具有电负性部分的烷基和亚甲基之一; 而BAS是一种生物活性物种。

14. 发明授权

US06870065B2 Bifunctional boronic compound complexing reagents and complexes 失效
标题翻译：双功能硼酸化合物络合物络合物
公开(公告)号：US06870065B2
公开(公告)日：2005-03-22
申请号：US10184836
申请日：2002-06-28
申请人： Clarence N. Ahlem , Robert J. Kaiser , Kevin P. Lund , Mark L. Stolowitz
发明人： Clarence N. Ahlem , Robert J. Kaiser , Kevin P. Lund , Mark L. Stolowitz
IPC分类号： C07C229/38 , C07C233/49 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , G01N33/543 , C07C255/00
CPC分类号： C07C233/49 , C07C229/38 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , G01N33/54353 , Y10S530/81 , Y10S530/816
摘要： A reagent having the general formula of General Formula I: wherein group R is an electrophilic or a nucleophilic moiety suitable for reaction of the reagent with a biologically active species; group R2 is one of H and OH moieties; group R3 is one of an alkyl and a methylene bearing an electronegative substituent; group Z is one of (CH2)n and CH2O(CH2CH2O)n2, and n is an integer of from 1 to 5, and n2 is an integer of from 1 to 4; and each of group Z2 and Z3 are (CH2)CONH(CH2)3CONH(CH2)2. Also, a reagent having the general formula of General Formula II: group R2 is one of H and OH moieties; group Z is one of (CH2)n and CH2O(CH2CH2O)n2, and n is an integer of from 1 to 5, and n2 is an integer of from 1 to 4; each of group Z2 and group Z3 include one of (CH2)CONH(CH2)3CONH(CH2)2; and (CH2)CONH(CH2); and group R is an electrophilic or a nucleophilic moiety suitable for reaction of the reagent with the biologically active species.
摘要翻译：具有通式I的通式的试剂：其中基团R是适于试剂与生物活性物质的反应的亲电子或亲核部分; 基团R2是H和OH部分之一; 基团R3是具有电负性取代基的烷基和亚甲基之一; 基团Z是（CH 2）n和CH 2 O（CH 2 CH 2 O）n 2中的一种，n是1至5的整数，n2是1至4的整数; Z 2和Z 3各自为（CH 2）CONH（CH 2）3 CONH（CH 2）2。另外，具有通式II：R2的通式的试剂是H和OH部分之一; 基团Z是（CH 2）n和CH 2 O（CH 2 CH 2 O）n 2中的一种，n是1至5的整数，n2是1至4的整数; Z 2和Z 3中的每一个包括（CH 2）CONH（CH 2）3 CONH（CH 2）2中的一个; 和（CH 2）CONH（CH 2）; 并且基团R是适于试剂与生物活性物质反应的亲电子或亲核部分。

15. 发明授权

US6013783A Boronic acid containing oligonucleotides and polynucleotides 失效
标题翻译：含硼酸的寡核苷酸和多核苷酸
公开(公告)号：US6013783A
公开(公告)日：2000-01-11
申请号：US272834
申请日：1999-03-19
申请人： Robert J. Kaiser , Mark L. Stolowitz
发明人： Robert J. Kaiser , Mark L. Stolowitz
IPC分类号： C07F9/6596 , C07H21/00 , C12N15/113 , C07H21/04 , C12P19/34
CPC分类号： C12N15/113 , C07F9/6596 , C07H21/00 , C12N2310/318 , C12N2310/33
摘要： The present invention relates to the field of nucleic acid immobilization, purification and detection and, more particularly, to boronic acid modified oligonucleotides and polynucleotides useful in bioconjugation reactions. The modified oligonucleotides and polynucleotides are useful in reactions for the immobilization and purification of macromolecules.
摘要翻译：本发明涉及核酸固定，纯化和检测领域，更具体地涉及可用于生物缀合反应的硼酸修饰的寡核苷酸和多核苷酸。修饰的寡核苷酸和多核苷酸可用于大分子固定和纯化的反应。

16. 发明授权

US5847192A Boronic compound complexing reagents and complexes 失效
标题翻译：硼化合物络合剂和配合物
公开(公告)号：US5847192A
公开(公告)日：1998-12-08
申请号：US689341
申请日：1996-08-05
申请人： Mark L. Stolowitz , Robert J. Kaiser , Kevin P. Lund , Steven M. Torkelson
发明人： Mark L. Stolowitz , Robert J. Kaiser , Kevin P. Lund , Steven M. Torkelson
IPC分类号： C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/44 , C07D207/452 , C07D207/46 , C07D213/71 , C07F5/02 , C07F5/04 , C07K5/02 , G01N33/543 , C07C233/50 , C07C233/46
CPC分类号： C07D207/452 , C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/46 , C07D213/71 , C07F5/025 , C07K5/0207 , G01N33/54353
摘要： Boron compound complexing reagents and methods of synthesizing these reagents are disclosed. These reagents, including those shown as General Formula I and General Formula II may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof. ##STR1##
摘要翻译：公开了硼化合物络合试剂和合成这些试剂的方法。在本文所述的进一步反应后，可以使用这些试剂，包括通式I和通式II所示的试剂，与硼酸化合物如苯基硼酸或其衍生物复合。一般公式I 通用二级

17. 发明授权

US5837878A Boronic compound complexing reagents and highly stable complexes 失效
标题翻译：硼化合物络合剂和高度稳定的络合物
公开(公告)号：US5837878A
公开(公告)日：1998-11-17
申请号：US689283
申请日：1996-08-05
申请人： Mark L. Stolowitz , Robert J. Kaiser , Kevin P. Lund
发明人： Mark L. Stolowitz , Robert J. Kaiser , Kevin P. Lund
IPC分类号： C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/44 , C07D207/452 , C07D207/46 , C07D213/71 , C07F5/02 , C07F5/04 , C07K5/02 , G01N33/543
CPC分类号： C07C233/51 , C07C229/38 , C07C233/49 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/452 , C07D207/46 , C07D213/71 , C07F5/025 , C07K5/0207 , G01N33/54353
摘要： Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIII, General Formula CIV, and General Formula CVI. In one embodiment, the reagents of General Formula CIII may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula CIV. The reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI. ##STR1##
摘要翻译：硼化合物络合剂，硼化合物络合物，以及合成这些试剂和络合物的方法。这些试剂和配合物包括通式CIII，通式CIV和通式CVI所示的试剂和络合物。在一个实施方案中，通式CIII的试剂可用于在与生物活性物质（BAS）缩合之后产生通式CIV的试剂。通式CIV的试剂可用于与硼化合物形成络合物，例如通式CVI所示的络合物。通用公式CIII 通用CIV 通用CVI

18. 发明授权

US5688928A Phenylboronic acid complexing reagents derived from aminosalicylic acid 失效
标题翻译：衍生自氨基水杨酸的苯硼酸络合试剂
公开(公告)号：US5688928A
公开(公告)日：1997-11-18
申请号：US480970
申请日：1995-06-07
申请人： Mark L. Stolowitz
发明人： Mark L. Stolowitz
IPC分类号： C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/44 , C07D207/452 , C07D207/46 , C07D213/71 , C07F5/02 , C07F5/04 , C07K5/02 , G01N33/543
CPC分类号： C07D207/452 , C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/46 , C07D213/71 , C07F5/025 , C07K5/0207 , G01N33/54353
摘要： The present invention relates to a novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moieties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.3, wherein group Y is selected from either O, S, and NH, and wherein group Z comprises a spacer which either separates the boronic acid complexing moiety from group R, as in General Formula I, or seperates two boronic acid complexing moieties, as in General Formula II. Group R is a reactive electrophilic or nucleophilic moiety suitable for reaction of the phenylboronic acid complexing reagent with a bioactive species.
摘要翻译：本发明涉及可用于制备生物缀合物的新一类苯基硼酸络合剂，以及制备和使用这些试剂的方法。在本发明中，代替现有技术的抗生物素蛋白 - 生物素和地高辛 - 抗地高辛系统，苯硼酸络合试剂与苯硼酸试剂（许多已知在现有技术中）一起使用，以促进化学共轭而没有使用中间生物大分子。适于修饰生物活性物质的试剂为通式I或通式II，其用于将苯硼酸络合部分并入用于随后缀合至具有侧苯基硼酸部分的不同生物活性物质的目的。通式I其中基团X选自H，OH，NH 2，NHCH 3，NHOH和NHOCH 3，其中基团Y选自O，S和NH，并且其中基团Z包括如通式I所示，将硼酸络合部分与基团R分开的间隔物，或分离两个硼酸络合部分，如通式II所示。基团R是适用于苯基硼酸络合试剂与生物活性物质反应的反应性亲电或亲核部分。

19. 发明授权

US5677431A Phenylboronic acid complexes for bioconjugate preparation 失效
标题翻译：苯硼酸复合物用于生物缀合物的制备
公开(公告)号：US5677431A
公开(公告)日：1997-10-14
申请号：US482886
申请日：1995-06-07
申请人： Mark L. Stolowitz
发明人： Mark L. Stolowitz
IPC分类号： C07F5/02 , G01N33/543
CPC分类号： C07F5/025 , G01N33/54353
摘要： The present invention relates to a novel class of phenylboronic acid bioconjugate complexes derived from aminosalicylic acid, and the method of making and using such bioconjugate complexes. The bioconjugate complexes are in the form of the following general formulas; ##STR1## wherein group X is selected from the group consisting of O, NH, N-alkyl, NC.sub.6 H.sub.5, N-aryl, NCH.sub.2 -aryl, NCH.sub.2 CH.sub.2 OH, NCOCH.sub.2 CH.sub.2 OH, NOH, NO-alkyl and NOCH.sub.2 -aryl, wherein alkyl denotes a hydrocarbon moiety of from 1 to 4 carbons in length and which may be linear or branched, wherein aryl is selected from the group consisting of an aromatic ring, a substituted aromatic ring and a fused aromatic ring, wherein group Y is selected from the group consisting of O, S, NH, N-alkyl, N-aryl and NCH.sub.2 -aryl, wherein groups Z and Z* comprise a spacer selected from an alkyl and a polyethyleneglycol chain, of from 1 to 16 carbon equivalents in length, wherein the chain may contain intermediate amide and disulfide bonds, and and wherein groups BAS and BAS* are bioactive species.
摘要翻译：本发明涉及一类新型的衍生自氨基水杨酸的苯基硼酸生物缀合物复合物，以及制备和使用这种生物缀合物复合物的方法。生物共轭配合物为下列通式的形式：通用化学式I GE>通式III + TR 通式IV + TR 其中基团X选自O，NH，N-烷基，NC6H5，N-芳基，NCH 2 - 芳基，NCH 2 CH 2 OH，NCOCH 2 CH 2 OH，NOH，NO-烷基和NOCH 2 - 芳基，其中烷基表示长度为1至4个碳的烃部分，其可以是直链或支链的，其中芳基选自芳香环，取代芳环和稠合芳环，其中基团Y选自O，S，NH，N-烷基，N-芳基和NCH 2 - 芳基，其中基团Z和Z *包含选自烷基和聚乙二醇链的间隔长度为1至16碳当量的链，其中该链可含有中间体酰胺和二硫键，并且其中gro

20. 发明授权

US5594151A Phenylboronic acid complexing reagents derived from aminosalicylic acid 失效
标题翻译：衍生自氨基水杨酸的苯硼酸络合试剂
公开(公告)号：US5594151A
公开(公告)日：1997-01-14
申请号：US188531
申请日：1994-01-28
申请人： Mark L. Stolowitz
发明人： Mark L. Stolowitz
IPC分类号： C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/44 , C07D207/452 , C07D207/46 , C07D213/71 , C07F5/02 , C07F5/04 , C07K5/02 , G01N33/543
CPC分类号： C07D207/452 , C07C229/38 , C07C233/49 , C07C233/51 , C07C237/12 , C07C237/22 , C07C255/13 , C07C259/10 , C07C271/22 , C07C281/02 , C07D207/46 , C07D213/71 , C07F5/025 , C07K5/0207 , G01N33/54353
摘要： The present invention relates to a novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of a bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moleties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.3, wherein group Y is selected from either O, S and NH, and wherein group Z comprises a spacer which either separates the boronic acid complexing moiety from group R, as in General Formula I, or seperates two boronic acid complexing moieties, as in General Formula II. Group R is a reactive electrophilic or nucleophilic moiety suitable for reaction of the phenylboronic acid complexing reagent with a bioactive species.
摘要翻译：本发明涉及可用于制备生物缀合物的新一类苯基硼酸络合剂，以及制备和使用这些试剂的方法。在本发明中，代替现有技术的抗生物素蛋白 - 生物素和地高辛 - 抗地高辛系统，苯硼酸络合试剂与苯硼酸试剂（许多已知在现有技术中）一起使用，以促进化学共轭而没有使用中间生物大分子。适于修饰生物活性物质的试剂为通式I或通式II，其用于将苯硼酸络合部分并入用于随后与不同具有侧苯基硼酸汽车侧生物活性物质的缀合物。通式I其中基团X选自H，OH，NH 2，NHCH 3，NHOH和NHOCH 3，其中基团Y选自O，S和NH，并且其中基团Z包含如通式I那样将硼酸络合部分与基团R分开的间隔物，或分离两个硼酸络合部分，如通式II所示。基团R是适用于苯基硼酸络合试剂与生物活性物质反应的反应性亲电或亲核部分。

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