ES2566761T3 - Ligación de azidas y acetilenos catalizada por cobre - Google Patents

Ligación de azidas y acetilenos catalizada por cobre Download PDF

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ES2566761T3
ES2566761T3 ES10005413.9T ES10005413T ES2566761T3 ES 2566761 T3 ES2566761 T3 ES 2566761T3 ES 10005413 T ES10005413 T ES 10005413T ES 2566761 T3 ES2566761 T3 ES 2566761T3
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ligation
metal
acetylene
copper
reaction
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Barry K. Sharpless
Valery Fokin
Vsevolod Rostovsev
Luke Green
Fahmi Himo
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Scripps Research Institute
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Scripps Research Institute
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
    • B01J2231/327—Dipolar cycloadditions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/16—Copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/96—Water

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Studio Devices (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Abstract

Un proceso que comprende el paso siguiente: catalizar una reacción de ligación química de clic entre una primera sustancia reaccionante que tiene un resto alquino terminal y segunda sustancia reaccionante que tiene un resto azida para formar un producto que tiene un resto triazol, realizándose la reacción de ligación química de clic en una solución en contacto con cobre metálico, actuando dicho cobre metálico como una fuente de Cu(I) catalítico para catálisis de la reacción de ligación química de clic.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
Efecto del ambiente reductor:
Cu(I) se oxida muy fácilmente a Cu(II) -fundamentalmente por acción del oxígeno, pero incluso oxidantes más suaves pueden realizar esto. Adicionalmente, Cu(I) media el acoplamiento oxidante de los acetiluros y otras
5 especies de cobre orgánico, lo que conduce a rendimientos reducidos y productos contaminados. Todos estos problemas pueden soslayarse por el uso de un agente reductor suave. Pueden utilizarse diversos agentes reductores: ascorbato, hidroquinona, otras quinonas (tales como vitamina K1), virutas/alambre de cobre, glutatión, cisteína, Fe2+, Co2++, etc. Puede emplearse virtualmente cualquier reductor que no sea tan potente como para reducir rápidamente Cu(II) a Cu(0).
10 Ligandos: Efecto del acetonitrilo:
Los metales no existen en soluciones "desnudas" -existen siempre ligandos presentes en la esfera de coordinación, se trate de moléculas de disolvente o ligandos 'de diseño'. Los ligandos tienen un efecto profundo sobre la 15 reactividad del centro metálico, así como las propiedades red/ox del metal: (a) aquéllos pueden estabilizar un determinado estado de oxidación del metal, v.g. Cu(I) es la forma deseable en el caso presente, y (b) de modo igualmente importante, pueden mantener la especie catalítica en la solución, haciendo con ello que la misma esté constantemente disponible para la catálisis. Ambos requerimientos citados tienen que cumplirse a fin de que una combinación metal/ligando sea útil en la catálisis de una cicloadición, o ligación de transformación deseada, en el
20 caso presente.
Transformaciones orgánicas mediadas por cobre han sido estudiadas durante más de 70 años, y la bibliografía acerca de esta cuestión es muy extensa. Una lección importante de la técnica anterior es que los cianuros y/o nitrilos son algunos de los mejores ligandos para Cu(I), que usualmente está tetracoordinado, formando complejos
-
25 tetraédricos. De hecho, el acetonitrilo se coordina con Cu(I) tan fuertemente que el complejo [Cu(CH3CN)4]+PF6 es una preparación de Cu(I) disponible comercialmente e insensible al oxígeno (es decir, este Cu(I) es inerte). Esta 'sobreestabilización' es claramente una desventaja cuando la meta es la reactividad. La reacción indicada a continuación ilustra este punto. Cuando se emplean mixturas agua/alcohol como disolventes (obsérvese que ambos son ligandos débiles para Cu(I)), la reacción se completa en menos de 6 horas. En cambio, cuando se utiliza como
30 disolvente acetonitrilo, no se observa reacción alguna en absoluto incluso después de 24 horas en condiciones por lo demás idénticas.
imagen6
35 Para explicar este fenómeno, recuérdese el mecanismo de la reacción. Con objeto de que transcurra la ligación, la azida tiene que coordinarse con el cobre (paso B1) y tiene que retirarse un ligando de la esfera de coordinación del metal, y en el caso de un acetonitrilo fuertemente coordinado, este paso es desventajoso.
7
imagen7
Por tanto, con objeto de tener una ventana de reactividad útil, deberían seleccionarse o diseñarse ligandos tales que se fijen relativamente bien al metal, y mantengan el mismo en el estado de oxidación correcto y en solución (es decir
5 no agregados hasta el punto de formar un precipitado polímero), pero que al mismo tiempo pueden separarse del centro metálico para permitir la formación del compuesto intermedio ii, lo cual es un paso necesario en la secuencia catalítica. Para usar este mismo ejemplo, la adición de una amina, tal como trietilamina o 2,6-lutidina al sistema de acetonitrilo arriba descrito, resuelve el problema de la reactividad -el producto se forma con rendimiento cuantitativo después de aprox. 8 horas.
10 Ligandos preferidos incluyen cianuros, nitrilos, isonitrilos, aminas primarias o secundarias, carboxilatos, haluros, alcoholes, y tioles. El cloruro es el haluro preferido y se emplea óptimamente a 1-5 M. Pueden emplearse también Los ligandos polivalentes que incluyen uno o más grupos funcionales seleccionados de nitrilo, isonitrilo, amina primaria o secundaria, carboxilato, alcohol, y tiol.
15 Otros Catalizadores Metálicos:
Cu no es el único metal capaz de catalizar este tipo de cicloadición. Con tal que se pueda formar el compuesto intermedio ii (es decir, si el metal está o puede llegar a estar coordinativamente insaturado), pueden emplearse
20 también otros metales conocidos que forman acetiluros estables. Metales ilustrativos que pueden formar acetiluros estables incluyen Cu, Au, Ag, Hg, Cd, Zr, Ru, Fe, Co, Pt, Pd, Ni, Rh, y W. Es cuestión de encontrar la combinación metal/ligando adecuada. El cobre es singular entre otros metales debido a que está soportado tan satisfactoriamente en sistemas acuosos que da como resultado un procedimiento experimental muy simple y una tolerancia extraordinaria a los grupos funcionales.
25 Catálisis de la Reacción de Ligación por el Recipiente Metálico:
Pueden utilizarse también recipientes metálicos como fuente de la especie catalítica para catalizar la reacción de ligación. Por ejemplo, puede emplearse un recipiente de cobre (Cu) para catalizar la reacción. Con objeto de
30 suministrar los iones necesarios, la solución de reacción tiene que establecer contacto físico con la superficie de cobre del recipiente. Alternativamente, la reacción puede ejecutarse en un recipiente no metálico, y los iones del metal catalítico pueden ser suministrados por contacto de la solución de reacción con un alambre de cobre, virutas de cobre u otras estructuras. Aunque estas reacciones pueden requerir más tiempo para llegar a su culminación, el procedimiento experimental es extraordinariamente simple. Por ejemplo, el bis-triazol representado en la entrada 2
35 (Figura 3A) se obtuvo con rendimiento cuantitativo después de agitar los componentes azida y acetileno correspondientes durante 24 h con aprox. 2 g de virutas de cobre metálico. Las virutas se retiraron al final de la reacción, y el producto blanco puro se recogió por filtración simple.
Agentes Reductores Alternativos:
40 Pueden emplearse metales como agentes reductores para mantener el estado de oxidación del catalizador Cu(I) o de otros catalizadores metálicos. Los agentes reductores metálicos preferidos incluyen Cu, Al, Be, Co, Cr, Fe, Mg,
8
imagen8

Claims (1)

  1. imagen1
ES10005413.9T 2002-05-30 2003-05-30 Ligación de azidas y acetilenos catalizada por cobre Expired - Lifetime ES2566761T3 (es)

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US385041P 2002-05-30

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US (8) US7375234B2 (es)
EP (2) EP1507769B2 (es)
JP (1) JP4638225B2 (es)
KR (2) KR101048279B1 (es)
CN (1) CN1671673B (es)
AT (1) ATE469135T1 (es)
AU (2) AU2003240482B2 (es)
CA (1) CA2487424C (es)
DE (1) DE60332725D1 (es)
DK (2) DK2226316T3 (es)
ES (2) ES2346646T5 (es)
HK (2) HK1073658A1 (es)
WO (1) WO2003101972A1 (es)

Families Citing this family (338)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK2226316T3 (en) * 2002-05-30 2016-04-11 Scripps Research Inst Copper catalyzed ligation of azides and acetylenes
US7601695B2 (en) 2003-03-10 2009-10-13 Optimer Pharmaceuticals, Inc. Antibacterial agents
WO2005058479A2 (en) 2003-12-17 2005-06-30 Praecis Pharmaceuticals, Inc. Methods for synthesis of encoded libraries
US7972994B2 (en) 2003-12-17 2011-07-05 Glaxosmithkline Llc Methods for synthesis of encoded libraries
JP4889505B2 (ja) 2004-02-02 2012-03-07 アンブレツクス・インコーポレイテツド 被修飾されたヒト成長ホルモンポリペプチドおよびこれらの使用
JP2008503217A (ja) 2004-06-18 2008-02-07 アンブレツクス・インコーポレイテツド 新規抗原結合ポリペプチド及びそれらの使用
AU2005260751A1 (en) * 2004-06-30 2006-01-12 The Scripps Research Institute Click chemistry route to triazole dendrimers
WO2009100255A2 (en) 2008-02-08 2009-08-13 Ambrx, Inc. Modified leptin polypeptides and their uses
CA2573561A1 (en) * 2004-07-22 2006-02-02 The Scripps Research Institute Polymeric materials via click chemistry
US7208243B2 (en) * 2004-12-01 2007-04-24 Toyota Technical Center Usa, Inc. Proton exchange membranes using cycloaddition reaction between azide and alkyne containing components
KR101224781B1 (ko) 2004-12-22 2013-01-21 암브룩스, 인코포레이티드 비천연적으로 코딩된 아미노산을 포함하는 인간 성장호르몬의 조제물
US8071718B2 (en) 2004-12-22 2011-12-06 General Electric Company Selective radiolabeling of biomolecules
JP2008525032A (ja) 2004-12-22 2008-07-17 アンブレツクス・インコーポレイテツド 組換えヒト成長ホルモンを発現及び精製するための方法
US20060172881A1 (en) * 2004-12-22 2006-08-03 Devaraj Neal K Method of spatially controlling catalysis of a chemical reaction
KR20070090023A (ko) 2004-12-22 2007-09-04 암브룩스, 인코포레이티드 변형 인간 성장 호르몬
WO2006068802A2 (en) 2004-12-22 2006-06-29 Ambrx, Inc. COMPOSITIONS OF AMINOACYL-tRNA SYNTHETASE AND USES THEREOF
GB0428012D0 (en) 2004-12-22 2005-01-26 Hammersmith Imanet Ltd Radiolabelling methods
CA2606094A1 (en) * 2005-04-27 2006-11-02 Siemens Medical Solutions Usa, Inc. The preparation of molecular imaging probes using click chemistry
US20060269942A1 (en) * 2005-04-27 2006-11-30 Kolb Hartmuth C In situ click chemistry method for screening high affinity molecular imaging probes
ATE479699T1 (de) * 2005-05-02 2010-09-15 Baseclick Gmbh Neue markierungsstrategien für den empfindlichen nachweis von analyten
KR101335218B1 (ko) 2005-05-02 2013-12-12 바스프 에스이 분석물의 감응성 검출을 위한 신규한 표지화 전략
CA2609205A1 (en) 2005-06-03 2006-12-14 Ambrx, Inc. Improved human interferon molecules and their uses
CN102392014A (zh) 2005-06-09 2012-03-28 葛兰素史克有限责任公司 合成编码文库的方法
US20070020620A1 (en) * 2005-07-14 2007-01-25 Finn M G Compositions and methods for coupling a plurality of compounds to a scaffold
US8158590B2 (en) 2005-08-05 2012-04-17 Syntarga B.V. Triazole-containing releasable linkers, conjugates thereof, and methods of preparation
ES2638427T3 (es) * 2005-08-24 2017-10-20 Melinta Therapeutics, Inc. Compuestos de triazol y procedimientos de preparación y uso del mismo
US20070060658A1 (en) * 2005-08-31 2007-03-15 Diaz David D Stabilization of organogels and hydrogels by azide-alkyne [3+2] cycloaddition
US7410899B2 (en) * 2005-09-20 2008-08-12 Enthone, Inc. Defectivity and process control of electroless deposition in microelectronics applications
JP4999850B2 (ja) * 2005-09-30 2012-08-15 ザ スクリプス リサーチ インスティチュート アルキンおよび有機アジドのルテニウム触媒環化付加
US7767421B2 (en) 2005-10-27 2010-08-03 President And Fellows Of Harvard College Methods and compositions for labeling nucleic acids
US7989395B2 (en) 2005-10-28 2011-08-02 Glaxosmithkline Llc Methods for identifying compounds of interest using encoded libraries
ES2547554T3 (es) 2005-11-16 2015-10-07 Ambrx, Inc. Métodos y composiciones que comprenden aminoácidos no naturales
DK2336315T3 (da) 2005-12-01 2017-11-06 Nuevolution As Fremgangsmåde til enzymatisk kodning ved effektiv syntese af store biblioteker
US8114636B2 (en) 2006-02-10 2012-02-14 Life Technologies Corporation Labeling and detection of nucleic acids
EP4092418A1 (en) 2006-02-10 2022-11-23 Life Technologies Corporation Oligosaccharide modification and labeling of proteins
EP1989242B1 (en) * 2006-02-21 2010-07-21 Huntsman International Llc Process for making a polyisocyanurate composite
WO2007130453A2 (en) * 2006-05-02 2007-11-15 Allozyne, Inc. Non-natural amino acid substituted polypeptides
US20080096819A1 (en) * 2006-05-02 2008-04-24 Allozyne, Inc. Amino acid substituted molecules
WO2007132005A2 (fr) * 2006-05-15 2007-11-22 Rhodia Operations Composés hybrides à base de polyol(s) et à base d'au moins une autre entité moléculaire, polymères ou non, notamment de type polyorganosiloxane, son procédé de préparation et ses applications
US20090253609A1 (en) * 2006-05-15 2009-10-08 Rhodia Operations Hybrid compounds based on silicones, and at least one other molecular entity, polymer or otherwise, especially of the polyol type, method for the preparation thereof, and applications of the same
FR2900929B1 (fr) * 2006-05-15 2012-11-16 Rhodia Recherches & Tech Composes hybrides a base de polyol(s) et a base d'au moins une autre entite moleculaire, polymeres ou non, notamment de type polyorganosiloxane, son procede de preparation et ses apllications
EP2029179A2 (en) 2006-06-21 2009-03-04 Hammersmith Imanet, Ltd Radiolabelling methods
EP2029616A1 (en) * 2006-06-21 2009-03-04 Hammersmith Imanet Limited Chemical methods and apparatus
US20100022481A1 (en) * 2006-08-02 2010-01-28 Dong Wang Drug Carriers, Their Synthesis, and Methods of Use Thereof
WO2008021290A2 (en) 2006-08-09 2008-02-21 Homestead Clinical Corporation Organ-specific proteins and methods of their use
US7772358B2 (en) * 2006-09-06 2010-08-10 The Hong Kong University Of Science And Technology Polytriazoles constructed by 1,3-dipolar cycloaddition
PT2064333E (pt) 2006-09-08 2014-06-09 Ambrx Inc Supressor híbrido arnt para células de vertebrados
EP2069396B1 (en) 2006-09-08 2015-10-21 Ambrx, Inc. Modified human plasma polypeptide or fc scaffolds and their uses
ITMI20061726A1 (it) * 2006-09-11 2008-03-12 Fidia Farmaceutici Derivati crosslinkati a base di acido ialuronico reticolato via click chemistry
US8080540B2 (en) 2006-09-19 2011-12-20 Abbott Products Gmbh Therapeutically active triazoles and their use
KR20090088371A (ko) * 2006-10-17 2009-08-19 헨켈 아게 운트 코. 카게아아 아지드 대 알킨의 1,3-양극성 고리첨가
CN101605743A (zh) 2006-10-31 2009-12-16 贝瑟克里科有限公司 用于产生报告分子的点击化学
US8288367B2 (en) 2006-11-30 2012-10-16 Solvay Pharmaceuticals Gmbh Substituted estratriene derivatives as 17BETA HSD inhibitors
EP2094721B1 (en) * 2006-12-14 2018-02-14 Aileron Therapeutics, Inc. Bis-sulfhydryl macrocyclization systems
US7981998B2 (en) * 2006-12-14 2011-07-19 Aileron Therapeutics, Inc. Bis-sulfhydryl macrocyclization systems
CA2939778C (en) 2007-01-31 2019-01-29 Dana-Farber Cancer Institute, Inc. Stabilized p53 peptides and uses thereof
ES2648687T3 (es) 2007-02-23 2018-01-05 Aileron Therapeutics, Inc. Péptidos macrocíclicos unidos a triazol
JP5551062B2 (ja) * 2007-03-22 2014-07-16 エージェンシー フォー サイエンス，テクノロジー アンド リサーチ シリカ系メソセル発泡体へのクリックケミストリーによる触媒の固定
CN101730708B (zh) 2007-03-28 2013-09-18 哈佛大学校长及研究员协会 缝合多肽
PL2068909T3 (pl) 2007-03-30 2012-09-28 Ambrx Inc Modyfikowane polipeptydy fgf-21 i ich zastosowanie
ATE479664T1 (de) * 2007-04-30 2010-09-15 Alcon Inc Uv-absorber für brillenglasmaterial
EP2076533B1 (en) 2007-05-02 2014-10-08 Ambrx, Inc. Modified interferon beta polypeptides and their uses
US8759508B2 (en) 2007-05-18 2014-06-24 Ge Healthcare Dharmacon, Inc. Chromophoric silyl protecting groups and their use in the chemical synthesis of oligonucleotides
KR101556802B1 (ko) 2007-07-26 2015-10-01 헨켈 아게 운트 코. 카게아아 이미드 부분을 함유하는 알콜, 및 이로부터 제조된 반응성 올리고머
TWI435915B (zh) * 2007-08-09 2014-05-01 Alcon Inc 含有吸收紫外光（ｕｖ）及短波長可見光二者的發色團之眼科鏡體材料（一）
TW200916531A (en) * 2007-08-09 2009-04-16 Alcon Inc Ophthalmic lens materials containing chromophores that absorb both UV and short wavelength visible light
CA2707840A1 (en) * 2007-08-20 2009-02-26 Allozyne, Inc. Amino acid substituted molecules
US8927682B2 (en) * 2007-08-24 2015-01-06 Board Of Trustees Of Michigan State University Functionalization of polyglycolides by “click” chemistry
US8394914B2 (en) * 2007-08-24 2013-03-12 Board Of Trustees Of Michigan State University Functional polyglycolide nanoparticles derived from unimolecular micelles
WO2009029253A1 (en) * 2007-08-27 2009-03-05 Theravance, Inc. Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists
CN101917850B (zh) * 2007-10-25 2016-01-13 森普拉制药公司 大环内酯类抗菌剂的制备方法
FR2923828B1 (fr) * 2007-11-16 2010-02-19 Rhodia Operations Composes hybrides a base de polyasaccharides(s) et d'au moins un polyoxyalkylene, leur procede de preparation et leurs applications
ES2632504T3 (es) 2007-11-20 2017-09-13 Ambrx, Inc. Polipéptidos de insulina modificados y sus usos
DK2222341T3 (en) 2007-11-21 2015-03-09 Univ Georgia AND METHODS alkynes of reacting alkynes of 1,3-dipole FUNCTIONAL COMPOUNDS
WO2009102378A2 (en) 2007-12-03 2009-08-20 Ge Healthcare Limited Purification of 68ge/68ga generator eluate from fe(iii) intended to improve specific radioactivity of 68ga-based radiopharmaceuticals
US9688718B2 (en) 2008-01-11 2017-06-27 Lawrence Livermore National Security, Llc Nanolipoprotein particles comprising hydrogenases and related products, methods and systems
JP5217457B2 (ja) * 2008-01-29 2013-06-19 国立大学法人 新潟大学 アジド−アルキン付加環化反応触媒及びそれを用いたトリアゾール化合物の製造方法
JP5158789B2 (ja) * 2008-03-31 2013-03-06 ダイキン工業株式会社 末端処理されたフッ化ビニリデン系ポリマーおよびフッ化ビニリデン系ポリマーセグメントを有するブロック共重合体ならびにその製造方法
US8034396B2 (en) * 2008-04-01 2011-10-11 Tyco Healthcare Group Lp Bioadhesive composition formed using click chemistry
US20090264317A1 (en) * 2008-04-18 2009-10-22 University Of Massachusetts Functionalized nanostructure, methods of manufacture thereof and articles comprising the same
WO2009140541A2 (en) * 2008-05-16 2009-11-19 Life Technologies Corporation Dual labeling methods for measuring cellular proliferation
WO2009143280A2 (en) * 2008-05-22 2009-11-26 Lawrence Livermore National Security, Llc Nanolipoprotein particles and related compositions, methods and systems
US8877676B2 (en) * 2008-07-09 2014-11-04 Postech Academy-Industry Foundation Heterogeneous copper nanocatalyst and manufacturing methods thereof
JP5680534B2 (ja) 2008-07-23 2015-03-04 イーライ リリー アンド カンパニー 修飾されているウシｇ−ｃｓｆポリペプチドおよびそれらの使用
WO2010010198A2 (en) * 2008-07-25 2010-01-28 Basf Se New azide substituted naphthylene or rylene imide derivatives and their use as reagents in click-reactions
US8618297B2 (en) 2008-07-25 2013-12-31 Basf Se Azide substituted naphthylene or rylene imide derivatives and their use as reagents in click-reactions
DE102008040886A1 (de) * 2008-07-31 2010-02-04 Wacker Chemie Ag Durch Click-Reaktion vernetzbare mehrkomponentige Siliconzusammensetzungen
GB0816783D0 (en) * 2008-09-15 2008-10-22 Carmeda Ab Immobilised biological entities
EP3587434A1 (en) * 2008-09-23 2020-01-01 Alnylam Pharmaceuticals Inc. Chemical modifications of monomers and oligonucleotides with click components for conjugation with ligands
PE20110832A1 (es) 2008-09-26 2011-11-24 Ambrx Inc Polipeptidos de eritropoyetina felina modificados
MX348657B (es) 2008-09-26 2017-06-21 Ambrx Inc Microorganismos y vacunas dependientes de replicacion de aminoacidos no naturales.
WO2010042555A2 (en) 2008-10-06 2010-04-15 The Brigham And Women's Hospital, Inc. Particles with multiple functionalized surface domains
ES2565083T3 (es) 2008-10-24 2016-03-31 Cempra Pharmaceuticals, Inc. Biodefensas usando macrólidos que contienen triazol
TWI453199B (zh) * 2008-11-04 2014-09-21 Alcon Inc 用於眼用鏡片材料之紫外光／可見光吸收劑
US20100203647A1 (en) * 2008-11-21 2010-08-12 The Rockefeller University Chemical Reporters of Protein Acylation
AU2010204648B2 (en) 2009-01-14 2016-09-01 Aileron Therapeutics, Inc. Peptidomimetic macrocycles
US20100189660A1 (en) * 2009-02-14 2010-07-29 Genentech, Inc. Methods for the detection of fatty-acylated protein
US8535477B2 (en) 2009-02-21 2013-09-17 Sofradim Production Medical devices incorporating functional adhesives
WO2010095047A2 (en) 2009-02-21 2010-08-26 Sofradim Production Apparatus and method of reacting polymers passing through metal ion chelated resin matrix to produce injectable medical devices
US9555154B2 (en) 2009-02-21 2017-01-31 Covidien Lp Medical devices having activated surfaces
US8512728B2 (en) 2009-02-21 2013-08-20 Sofradim Production Method of forming a medical device on biological tissue
US8663689B2 (en) 2009-02-21 2014-03-04 Sofradim Production Functionalized adhesive medical gel
WO2010095055A1 (en) 2009-02-21 2010-08-26 Sofradim Production Crosslinked fibers and method of making same using uv radiation
EP2398524B1 (en) 2009-02-21 2017-07-12 Covidien LP Medical devices having activated surfaces
US8968733B2 (en) 2009-02-21 2015-03-03 Sofradim Production Functionalized surgical adhesives
AU2010215203B2 (en) 2009-02-21 2015-07-16 Covidien Lp Medical devices with an activated coating
WO2010095053A2 (en) 2009-02-21 2010-08-26 Sofradim Production Apparatus and method of reaching polymers by exposure to uv radiation to produce injectable medical devices
EP2398845B1 (en) 2009-02-21 2017-12-13 Sofradim Production Amphiphilic compounds and self-assembling compositions made therefrom
US8877170B2 (en) 2009-02-21 2014-11-04 Sofradim Production Medical device with inflammatory response-reducing coating
EP2398519A2 (en) 2009-02-21 2011-12-28 Sofradim Production Compounds and medical devices activated with solvophobic linkers
CA2753179A1 (en) 2009-02-21 2010-08-26 Sofradim Production Crosslinked fibers and method of making same by extrusion
CA2752884A1 (en) * 2009-02-27 2010-09-02 Genentech, Inc. Methods and compositions for protein labelling
EP2405757B8 (en) 2009-03-11 2017-12-13 ISP Investments LLC Functionalized 4- and 5-vinyl substituted regioisomers of 1,2,3-triazoles via 1,3-dipolar cycloaddition and polymers thereof
US20100240594A1 (en) * 2009-03-20 2010-09-23 Burnham Institute For Medical Research Targeted delivery of chemotherapeutic agents
WO2010127088A2 (en) * 2009-04-29 2010-11-04 Massachusetts Institute Of Technology Intramolecular azide-alkyne cycloaddition
EA022699B1 (ru) 2009-05-27 2016-02-29 Селекта Байосайенсиз, Инк. НАЦЕЛЕННЫЕ СИНТЕТИЧЕСКИЕ НАНОНОСИТЕЛИ С pH-ЧУВСТВИТЕЛЬНЫМ ВЫСВОБОЖДЕНИЕМ ИММУНОМОДУЛИРУЮЩИХ СРЕДСТВ
EP2435461B1 (en) 2009-05-29 2017-08-09 Life Technologies Corporation Scaffolded nucleic acid polymer particles and methods of making and using
US9937194B1 (en) 2009-06-12 2018-04-10 Cempra Pharmaceuticals, Inc. Compounds and methods for treating inflammatory diseases
US8247614B2 (en) * 2009-06-17 2012-08-21 E I Du Pont De Nemours And Company Copolycondensation polymerization of fluoropolymers
EP2451286B8 (en) * 2009-07-08 2018-04-04 ISP Investments LLC 4- and 5 substituted 1,2,3- triazole moieties with at least one remote polymerizable moiety and polymers thereof
WO2011009934A1 (en) 2009-07-24 2011-01-27 Institut Català D'investigació Química (Iciq) Tris(1,2,3-triazol-4-yl)methane organometallic compounds as catalysts and processes using them.
JP5774587B2 (ja) * 2009-08-11 2015-09-09 ザ スクリプス リサーチ インスティテュート 有機アジドおよび１−ハロアルキンの銅触媒による付加環化
CN108310000A (zh) 2009-09-10 2018-07-24 森普拉制药公司 治疗疟疾、结核病和mac疾病的方法
US20110065809A1 (en) * 2009-09-15 2011-03-17 Medtronic, Inc. Polymerization of Multifunctional Azides, and Polymers Therefrom
CA2774973A1 (en) 2009-09-22 2011-03-31 Aileron Therapeutics, Inc. Peptidomimetic macrocycles
US20110129834A1 (en) * 2009-11-24 2011-06-02 Life Technologies Corporation Selective amplification of polynucleotide sequences
GB0921665D0 (en) 2009-12-10 2010-01-27 Trillion Genomics Ltd Phobes
US8765432B2 (en) 2009-12-18 2014-07-01 Oligasis, Llc Targeted drug phosphorylcholine polymer conjugates
CN102666578A (zh) 2009-12-21 2012-09-12 Ambrx公司 经过修饰的猪促生长素多肽和其用途
EA201290541A1 (ru) 2009-12-21 2013-05-30 Амбркс, Инк. Модифицированные бычьи соматотропиновые полипептиды и их применение
GB201001088D0 (en) 2010-01-23 2010-03-10 Trillion Genomics Ltd Detection
ITFI20100019A1 (it) 2010-02-12 2011-08-13 Univ Firenze Inibitori peptidomimetici di integrine basati sull'1,2,3-triazolo per la diagnosi e terapia dei tumori.
US20110210017A1 (en) * 2010-03-01 2011-09-01 Lai Rebecca Y Fabrication of electrochemical biosensors via click chemistry
GB201004101D0 (en) 2010-03-12 2010-04-28 Carmeda Ab Immobilised biological entities
CN103080122A (zh) 2010-03-22 2013-05-01 森普拉制药公司 大环内脂的结晶形式及其用途
US9180221B2 (en) 2010-03-25 2015-11-10 Covidien Lp Functionalized adhesive for medical devices
CA2794335A1 (en) 2010-03-25 2011-09-29 Sofradim Production Medical devices incorporating functional adhesives
CA2794336A1 (en) 2010-03-25 2011-09-29 Sofradim Production Surgical fasteners and methods for sealing wounds
CA2794522C (en) 2010-04-05 2019-11-26 Prognosys Biosciences, Inc. Spatially encoded biological assays
US20190300945A1 (en) 2010-04-05 2019-10-03 Prognosys Biosciences, Inc. Spatially Encoded Biological Assays
US10787701B2 (en) 2010-04-05 2020-09-29 Prognosys Biosciences, Inc. Spatially encoded biological assays
EP3549963B1 (en) 2010-04-15 2022-01-12 Kodiak Sciences Inc. High molecular weight zwitterion-containing polymers
EP3540059A1 (en) 2010-04-16 2019-09-18 Nuevolution A/S Bi-functional complexes and methods for making and using such complexes
RU2608390C2 (ru) 2010-05-20 2017-01-18 Семпра Фармасьютикалз, Инк. Способы получения макролидов и кетолидов, и промежуточных соединений для их получения
US8394351B2 (en) * 2010-05-25 2013-03-12 Lawrence Livermore National Security, Llc Synthesis of triazole-based and imidazole-based zinc catalysts
US9636423B2 (en) 2010-06-02 2017-05-02 The General Hospital Corporation Optical sensor conjugates for detecting reactive oxygen and/or reactive nitrogen species in vivo
EP2588525A4 (en) 2010-06-29 2015-06-10 Covidien Lp MICROWAVE POWERED REACTOR AND IN SITU IMPLANT TRAINING METHOD
CA2804251A1 (en) 2010-07-01 2012-01-05 Sofradim Production Medical device with predefined activated cellular integration
EP2598178B1 (en) 2010-07-27 2018-07-11 Sofradim Production Polymeric fibers having tissue reactive members
WO2012016048A1 (en) 2010-07-28 2012-02-02 Life Technologies Corporation Anti- viral azide-containing compounds
US20120028335A1 (en) 2010-07-28 2012-02-02 Life Technologies Corporation Anti-viral azide-containing compounds
SI2603600T1 (sl) 2010-08-13 2019-04-30 Aileron Therapeutics, Inc. Peptidomimetični makrocikli
US9567386B2 (en) 2010-08-17 2017-02-14 Ambrx, Inc. Therapeutic uses of modified relaxin polypeptides
CA2808596C (en) 2010-08-17 2020-12-15 Ambrx, Inc. Modified relaxin polypeptides and their uses
KR20130120458A (ko) 2010-09-10 2013-11-04 셈프라 파마슈티컬스, 인크. 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드
AR083006A1 (es) 2010-09-23 2013-01-23 Lilly Co Eli Formulaciones para el factor estimulante de colonias de granulocitos (g-csf) bovino y variantes de las mismas
WO2012061717A1 (en) 2010-11-05 2012-05-10 Selecta Biosciences, Inc. Modified nicotinic compounds and related methods
EP3156480B1 (en) 2011-02-07 2020-03-25 Life Technologies Corporation Compositions and methods for stabilizing susceptible compounds
EP2966061B1 (en) 2011-03-04 2017-05-03 Life Technologies Corporation Compounds and methods for conjugation of biomolecules
JP2014509859A (ja) 2011-03-16 2014-04-24 アムジエン・インコーポレーテツド １７ｎａｖ１．３およびｎａｖ１．７の強力かつ選択的阻害剤
US9145361B2 (en) 2011-03-25 2015-09-29 Life Technologies Corporation SDP-containing heterobifunctional agents
EP2712291A4 (en) 2011-04-06 2014-11-05 Scripps Research Inst N1 AND N2 CARBAMOYL-1,2,3-TRIAZOL SERINE HYDROLASE INHIBITORS AND METHOD THEREFOR
GB201106254D0 (en) 2011-04-13 2011-05-25 Frisen Jonas Method and product
US20140170653A1 (en) 2011-04-15 2014-06-19 Life Technologies Corporation Chemical ligation
WO2012149259A1 (en) 2011-04-29 2012-11-01 Selecta Biosciences, Inc. Tolerogenic synthetic nanocarriers to reduce antibody responses
CN103732619A (zh) 2011-05-31 2014-04-16 普罗拜奥金股份有限公司 用于制备具有毒素、佐剂、检测标签和药代动力学半衰期延长剂的蛋白质的岩藻糖连接位点特异性缀合物的方法
CN102336643B (zh) * 2011-07-13 2014-06-25 北京博源恒升高科技有限公司 苯酚类直接氧化合成苯醌类的工艺
CN102335568B (zh) * 2011-07-22 2013-12-04 浙江大学 一种含三唑环的季铵盐型阳离子表面活性剂及其合成方法
US9040678B2 (en) 2011-08-05 2015-05-26 Illumina, Inc. Functionalization and purification of molecules by reversible group exchange
AU2012296937B2 (en) 2011-08-17 2017-10-12 Merck & Cie Folate conjugates of albumin-binding entities
CA2839654C (en) 2011-08-22 2021-02-16 Merck & Cie 18f-saccharide-folates
US20130066063A1 (en) 2011-09-09 2013-03-14 John Cooke Hodges Bicyclo[6.1.0]non-4-yne regents for chemical modification of oligonucleotides
US10378051B2 (en) 2011-09-29 2019-08-13 Illumina Cambridge Limited Continuous extension and deblocking in reactions for nucleic acids synthesis and sequencing
US8846899B2 (en) 2011-10-12 2014-09-30 Anatrace Products, Llc Maltoside and phosphocholine derivatives, uses thereof and methods of preparing artificial lipid structures thereof
WO2013059475A1 (en) 2011-10-18 2013-04-25 Life Technologies Corporation Alkynyl-derivatized cap analogs, preparation and uses thereof
WO2013059525A1 (en) 2011-10-18 2013-04-25 Aileron Therapeutics, Inc. Peptidomimetic macrocyles
EP3305400A3 (en) 2011-10-28 2018-06-06 Illumina, Inc. Microarray fabrication system and method
US9644038B2 (en) 2011-12-21 2017-05-09 The Regents Of The University Of California Apolipoprotein nanodiscs with telodendrimer
WO2013092998A1 (en) 2011-12-23 2013-06-27 Innate Pharma Enzymatic conjugation of antibodies
US20140357871A1 (en) 2012-01-10 2014-12-04 Lupin Limited Process for preparation of rufinamide
EP2807252B1 (en) 2012-01-26 2017-05-10 Life Technologies Corporation Methods for increasing the infectivity of viruses
CN108912211A (zh) 2012-02-15 2018-11-30 爱勒让治疗公司 三唑交联的和硫醚交联的拟肽大环化合物
SG11201404648PA (en) 2012-02-15 2014-09-26 Aileron Therapeutics Inc Peptidomimetic macrocycles
NO2694769T3 (es) 2012-03-06 2018-03-03
KR20140139083A (ko) 2012-03-27 2014-12-04 셈프라 파마슈티컬스, 인크. 마크롤라이드계 항생제를 투여하기 위한 비경구 제제
US9012022B2 (en) 2012-06-08 2015-04-21 Illumina, Inc. Polymer coatings
EP2680005A1 (en) 2012-06-28 2014-01-01 Rheinische Friedrich-Wilhelms-Universität Bonn Lipid analysis
US10132799B2 (en) 2012-07-13 2018-11-20 Innate Pharma Screening of conjugated antibodies
US9758606B2 (en) 2012-07-31 2017-09-12 The Trustees Of Columbia University In The City Of New York Cyclopropenium polymers and methods for making the same
EP2912459A2 (en) 2012-10-25 2015-09-02 Life Technologies Corporation Methods and compositions for enzyme-mediated site-specific radiolabeling of glycoproteins
EP2914256B1 (en) 2012-11-01 2019-07-31 Aileron Therapeutics, Inc. Disubstituted amino acids and methods of preparation and use thereof
WO2014072482A1 (en) 2012-11-09 2014-05-15 Innate Pharma Recognition tags for tgase-mediated conjugation
US9925303B2 (en) 2012-11-13 2018-03-27 Edwards Lifesciences Corporation Methods for cross-linking bioprosthetic tissue using bio-orthogonal binding pairs
WO2014093552A1 (en) * 2012-12-12 2014-06-19 The Regents Of The University Of California Rapid discovery and screening of enzyme activity using mass spectrometry
CN103058942B (zh) * 2012-12-20 2015-05-13 江苏城市职业学院 一种1,2,3-三氮唑化合物的一锅法合成方法
JP2016507520A (ja) 2013-01-23 2016-03-10 ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー 安定化されたｂ型肝炎コアポリペプチド
US9255255B2 (en) 2013-03-04 2016-02-09 The Board Of Trustees Of The Leland Stanford Junior University Synthesis of linear and branched polymers of polypeptides through direct conjugation
US10344060B2 (en) 2013-03-12 2019-07-09 Amgen Inc. Potent and selective inhibitors of Nav1.7
US9636418B2 (en) 2013-03-12 2017-05-02 Amgen Inc. Potent and selective inhibitors of NAV1.7
JP6426696B2 (ja) 2013-03-14 2018-11-21 センプラ ファーマシューティカルズ，インコーポレイテッド 呼吸器疾患の治療のための方法および製剤
AU2014233240B2 (en) 2013-03-15 2018-08-09 Cempra Pharmaceuticals, Inc. Convergent processes for preparing macrolide antibacterial agents
US10611824B2 (en) 2013-03-15 2020-04-07 Innate Pharma Solid phase TGase-mediated conjugation of antibodies
JP2016517275A (ja) 2013-03-15 2016-06-16 ザ キュレイターズ オブ ザ ユニバーシティ オブ ミズーリ 多重核酸検出のためのコード化ナノポアセンサー
WO2014146575A1 (en) 2013-03-19 2014-09-25 Beijing Shenogen Pharma Group Ltd. Antibodies and methods for treating estrogen receptor-associated diseases
US9775928B2 (en) 2013-06-18 2017-10-03 Covidien Lp Adhesive barbed filament
EP3010547B1 (en) 2013-06-20 2021-04-21 Innate Pharma Enzymatic conjugation of polypeptides
KR20160042871A (ko) 2013-06-21 2016-04-20 이나뜨 파르마, 에스.아. 폴리펩티드의 효소적 콘쥬게이션
EP3013984B1 (en) 2013-06-25 2023-03-22 Prognosys Biosciences, Inc. Methods for determining spatial patterns of biological targets in a sample
EP2818867A1 (en) 2013-06-27 2014-12-31 INSERM (Institut National de la Santé et de la Recherche Médicale) Antibodies conjugated to at least one nucleic acid molecule and their use in multiplex immuno-detection assays
WO2015002789A1 (en) 2013-07-03 2015-01-08 Illumina, Inc. Sequencing by orthogonal synthesis
CN103467394B (zh) * 2013-08-30 2015-07-01 河南师范大学 一种制备1,2,3-三氮唑类化合物的方法
US20160199832A1 (en) 2013-08-30 2016-07-14 Advanced Liquid Logic France Sas Manipulation of droplets on hydrophilic or variegated-hydrophilic surfaces
CN103558215B (zh) * 2013-11-06 2016-05-18 中国科学院广州生物医药与健康研究院 一种基于点击化学和g四聚体的铜离子检测试剂盒以及检测方法
EP3079668A1 (en) 2013-12-09 2016-10-19 Durect Corporation Pharmaceutically active agent complexes, polymer complexes, and compositions and methods involving the same
ES2803079T3 (es) 2014-09-12 2021-01-22 Illumina Inc Métodos para detectar la presencia de subunidades de polímeros usando quimioluminiscencia
WO2016049061A1 (en) 2014-09-22 2016-03-31 Lawrence Livermore National Security, Llc Electrochemical flow-cell for hydrogen production and nicotinamide co-factor dependent target reduction, and related methods and systems
EP3197478A4 (en) 2014-09-24 2018-05-30 Aileron Therapeutics, Inc. Peptidomimetic macrocycles and uses thereof
BR112017005736A2 (pt) 2014-09-24 2017-12-12 Aileron Therapeutics Inc macrociclos peptidomiméticos e formulações dos mesmos
US9879283B2 (en) 2014-10-09 2018-01-30 Life Technologies Corporation CRISPR oligonucleotides and gene editing
JP6702962B2 (ja) 2014-10-24 2020-06-03 ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ 改変ｆｇｆ−２１ポリペプチドおよびその使用
US20170306306A1 (en) 2014-10-24 2017-10-26 Life Technologies Corporation Compositions and Methods for Enhancing Homologous Recombination
PH12017500935A1 (en) 2014-11-21 2017-11-27 Merck Sharp & Dohme Insulin receptor partial agonists
NL2013857B1 (en) 2014-11-21 2016-10-11 Piculet Biosciences Tech B V Self-assembled bivalent ligand complex (SABLC) libraries and methods for screening such libraries.
EP3230393B1 (en) * 2014-12-12 2019-04-24 Marcella Chiari New clickable polymers and gels for microarray and other applications
EP3882356A1 (en) 2014-12-15 2021-09-22 Illumina, Inc. Compositions and methods for single molecular placement on a substrate
JP6773677B2 (ja) 2015-03-17 2020-10-21 アローヘッド ファーマシューティカルズ インコーポレイテッド 改善されたジスルフィド含有アルキン連結剤
EP3270704A1 (en) 2015-03-18 2018-01-24 Cargill, Incorporated Low-fat water-in-oil emulsion
US10253067B2 (en) 2015-03-20 2019-04-09 Aileron Therapeutics, Inc. Peptidomimetic macrocycles and uses thereof
EP3783109B1 (en) 2015-03-31 2024-05-29 Illumina Cambridge Limited Surface concatamerization of templates
EP3901282B1 (en) 2015-04-10 2023-06-28 Spatial Transcriptomics AB Spatially distinguished, multiplex nucleic acid analysis of biological specimens
FI3760737T3 (fi) 2015-05-11 2023-07-17 Illumina Inc Alusta lääkinnällisten aineiden löytämiseen ja analysoimiseen
US10590464B2 (en) 2015-05-29 2020-03-17 Illumina Cambridge Limited Enhanced utilization of surface primers in clusters
WO2016196492A1 (en) * 2015-06-01 2016-12-08 Occidental College Methods, compositions, and kits using heterogeneous catalysts
PL236024B1 (pl) 2015-06-08 2020-11-30 Univ Jagiellonski Pochodna 1,2,3-triazolilocyklohesan-1-olu i ich zastosowanie
US10059741B2 (en) 2015-07-01 2018-08-28 Aileron Therapeutics, Inc. Peptidomimetic macrocycles
CN104945340B (zh) * 2015-07-15 2017-09-19 河南师范大学 乙酰丙酮铜（ii）催化合成1,2,3‑三氮唑类化合物的方法
US10913975B2 (en) 2015-07-27 2021-02-09 Illumina, Inc. Spatial mapping of nucleic acid sequence information
RU2742955C2 (ru) 2015-07-30 2021-02-12 Иллюмина, Инк. Ортогональное деблокирование нуклеотидов
US10023613B2 (en) 2015-09-10 2018-07-17 Aileron Therapeutics, Inc. Peptidomimetic macrocycles as modulators of MCL-1
US11279749B2 (en) 2015-09-11 2022-03-22 Lawrence Livermore National Security, Llc Synthetic apolipoproteins, and related compositions methods and systems for nanolipoprotein particles formation
EP3370771A4 (en) 2015-11-03 2019-06-19 Ambrx, Inc. ANTI-CD3-FOLATE CONJUGATES AND USES THEREOF
EP3374337B1 (en) 2015-11-11 2021-03-17 SABIC Global Technologies B.V. Methods and systems for purifying 1,3-butadiene from a c4 hydrocarbon stream
CN109415729B (zh) 2016-04-21 2022-12-09 生命技术公司 具有降低毒性的基因编辑试剂
WO2017189342A1 (en) 2016-04-26 2017-11-02 Merck Sharp & Dohme Corp. Insulin dimer-incretin conjugates
EP3463429A4 (en) 2016-05-24 2020-07-22 Merck Sharp & Dohme Corp. PARTIAL INSULIN RECEPTOR AGONISTS AND GLP-1 ANALOGUES
EP3472210A1 (en) 2016-06-17 2019-04-24 Life Technologies Corporation Site-specific crosslinking of antibodies
US20210072255A1 (en) 2016-12-16 2021-03-11 The Brigham And Women's Hospital, Inc. System and method for protein corona sensor array for early detection of diseases
DE202017007366U1 (de) 2016-12-16 2021-02-17 The Brigham And Women's Hospital, Inc. Sensor-Array zum Erfassen einer relativen Proteinkonzentration
EP3565900B1 (en) 2017-01-20 2021-04-07 Omniome, Inc. Genotyping by polymerase binding
EP3571313B1 (en) 2017-01-20 2020-12-23 Omniome, Inc. Allele-specific capture of nucleic acids
CN110637027A (zh) 2017-02-08 2019-12-31 百时美施贵宝公司 包含药代动力学增强子的修饰的松弛素多肽及其用途
US11492666B2 (en) 2017-02-15 2022-11-08 Pacific Biosciences Of California, Inc. Distinguishing sequences by detecting polymerase dissociation
US20200149034A1 (en) 2017-03-17 2020-05-14 Hitgen Ltd. Methods and Compositions for Synthesis of Encoded Libraries
WO2018175788A1 (en) 2017-03-22 2018-09-27 Genentech, Inc. Hydrogel cross-linked hyaluronic acid prodrug compositions and methods
US11207422B2 (en) 2017-05-02 2021-12-28 Lawrence Livermore National Security, Llc MOMP telonanoparticles, and related compositions, methods and systems
CN107162991B (zh) * 2017-06-30 2020-05-22 武汉工程大学 一种溶剂参与反应合成4-乙酰基-1,2,3-三唑化合物的方法
CN107353256B (zh) * 2017-06-30 2020-05-22 武汉工程大学 一锅法合成4-乙酰基-1,2,3-三唑化合物的方法
CA3070407C (en) 2017-07-18 2022-08-09 Omniome, Inc. Method of chemically modifying plastic surfaces
BR112020004041A2 (pt) * 2017-09-29 2020-09-08 Baseclick Gmbh ligação com base click
EP3461832A1 (en) * 2017-09-29 2019-04-03 baseclick GmbH Click based ligation
WO2019092148A1 (en) 2017-11-10 2019-05-16 Innate Pharma Antibodies with functionalized glutamine residues
EP3775196A4 (en) 2018-04-04 2021-12-22 Nautilus Biotechnology, Inc. NANOREWAL AND MICROREWAL GENERATION PROCESSES
AU2019276719A1 (en) 2018-05-31 2020-11-26 Pacific Biosciences Of California, Inc. Increased signal to noise in nucleic acid sequencing
WO2020018613A1 (en) * 2018-07-17 2020-01-23 Wake Forest University Health Sciences Compounds useful for in vivo imaging of protein oxidation and/or cancer treatment
EP3844306A2 (en) 2018-08-28 2021-07-07 10X Genomics, Inc. Increasing spatial array resolution
US11519033B2 (en) 2018-08-28 2022-12-06 10X Genomics, Inc. Method for transposase-mediated spatial tagging and analyzing genomic DNA in a biological sample
AU2019327456A1 (en) 2018-08-28 2021-04-15 Ambrx, Inc. anti-CD3 antibody folate bioconjugates and their uses
WO2020047005A1 (en) 2018-08-28 2020-03-05 10X Genomics, Inc. Resolving spatial arrays
CN109320686B (zh) * 2018-08-29 2021-06-08 华南理工大学 一种聚异脲类聚合物及其制备方法和应用
PL3849614T3 (pl) 2018-09-11 2024-04-22 Ambrx, Inc. Koniugaty polipeptydu interleukiny-2 i ich zastosowania
CN109134881B (zh) * 2018-09-18 2021-01-26 中原工学院 一种基于铜配合物非均相催化材料的制备方法及应用
JP2022512746A (ja) 2018-10-19 2022-02-07 アンブルックス，インコーポレイテッド インターロイキン－１０ポリペプチド複合体、その二量体、およびそれらの使用
SG11202105824RA (en) 2018-12-10 2021-06-29 10X Genomics Inc Imaging system hardware
US11649485B2 (en) 2019-01-06 2023-05-16 10X Genomics, Inc. Generating capture probes for spatial analysis
US11926867B2 (en) 2019-01-06 2024-03-12 10X Genomics, Inc. Generating capture probes for spatial analysis
WO2020168017A1 (en) 2019-02-12 2020-08-20 Ambrx, Inc. Compositions containing, methods and uses of antibody-tlr agonist conjugates
WO2020167574A1 (en) 2019-02-14 2020-08-20 Omniome, Inc. Mitigating adverse impacts of detection systems on nucleic acids and other biological analytes
WO2020176788A1 (en) 2019-02-28 2020-09-03 10X Genomics, Inc. Profiling of biological analytes with spatially barcoded oligonucleotide arrays
CN109897010B (zh) * 2019-03-04 2021-02-19 天津凯莱英制药有限公司 一种1,2,3-三氮唑类化合物的连续合成方法
EP3938538A1 (en) 2019-03-15 2022-01-19 10X Genomics, Inc. Methods for using spatial arrays for single cell sequencing
WO2020198071A1 (en) 2019-03-22 2020-10-01 10X Genomics, Inc. Three-dimensional spatial analysis
EP3976820A1 (en) 2019-05-30 2022-04-06 10X Genomics, Inc. Methods of detecting spatial heterogeneity of a biological sample
US11739316B2 (en) 2019-06-21 2023-08-29 Thermo Fisher Scientific Baltics Uab Oligonucleotide-tethered nucleotides
JP2022542839A (ja) 2019-07-19 2022-10-07 フラッグシップ パイオニアリング イノベーションズ シックス，エルエルシー リコンビナーゼ組成物及び使用方法
CN117233413A (zh) 2019-08-05 2023-12-15 禧尔公司 用于样品制备、数据生成和蛋白质冠分析的系统和方法
EP4038546A1 (en) 2019-10-01 2022-08-10 10X Genomics, Inc. Systems and methods for identifying morphological patterns in tissue samples
WO2021072265A1 (en) 2019-10-10 2021-04-15 Kodiak Sciences Inc. Methods of treating an eye disorder
CN114599795A (zh) 2019-10-18 2022-06-07 加利福尼亚太平洋生物科学股份有限公司 用于对核酸加帽的方法和组合物
CN110790812A (zh) * 2019-11-08 2020-02-14 安徽易康达光电科技有限公司 一种皮肤胆固醇检测的试剂及其制备方法
EP4055185A1 (en) 2019-11-08 2022-09-14 10X Genomics, Inc. Spatially-tagged analyte capture agents for analyte multiplexing
WO2021097255A1 (en) 2019-11-13 2021-05-20 10X Genomics, Inc. Generating capture probes for spatial analysis
CA3158603A1 (en) 2019-11-18 2021-05-27 Neil Ira WEISENFELD Systems and methods for tissue classification
AU2020388573A1 (en) 2019-11-21 2022-06-23 10X Genomics, Inc, Spatial analysis of analytes
CA3158891A1 (en) 2019-11-22 2021-05-27 Neil Ira WEISENFELD Systems and methods for spatial analysis of analytes using fiducial alignment
AU2021213421A1 (en) 2020-01-31 2022-06-23 Innate Pharma Treatment of cancer
WO2021168287A1 (en) 2020-02-21 2021-08-26 10X Genomics, Inc. Methods and compositions for integrated in situ spatial assay
WO2021173889A1 (en) 2020-02-26 2021-09-02 Ambrx, Inc. Uses of anti-cd3 antibody folate bioconjugates
EP4114966A1 (en) 2020-03-03 2023-01-11 Pacific Biosciences Of California, Inc. Methods and compositions for sequencing double stranded nucleic acids
JP2023517595A (ja) 2020-03-11 2023-04-26 アンブルックス，インコーポレイテッド インターロイキン－２ポリペプチド結合物およびその使用方法
US20230235379A1 (en) 2020-04-30 2023-07-27 Dimensiongen Devices and methods for macromolecular manipulation
EP4150067A2 (en) 2020-05-11 2023-03-22 Thermo Fisher Scientific Baltics Uab Mutant polymerases and methods of using the same
US20230321653A1 (en) 2020-06-01 2023-10-12 Dimensiongen Devices and methods for cytogenetic analysis
CN114057658A (zh) * 2020-07-31 2022-02-18 中国科学院上海有机化学研究所 一种多三氮唑类化合物、其制备方法及应用
WO2022031955A1 (en) 2020-08-06 2022-02-10 Illumina, Inc. Preparation of rna and dna sequencing libraries using bead-linked transposomes
EP4200416A1 (en) 2020-08-18 2023-06-28 Illumina, Inc. Sequence-specific targeted transposition and selection and sorting of nucleic acids
US20230302150A1 (en) 2020-08-20 2023-09-28 Ambrx, Inc. Antibody-tlr agonist conjugates, methods and uses thereof
EP4237573A1 (en) 2020-10-29 2023-09-06 DNA Script Enzymatic synthesis of polynucleotide probes
JP2023549350A (ja) 2020-11-11 2023-11-24 ノーティラス・サブシディアリー・インコーポレイテッド 向上した結合及び検出特徴を有する親和性試薬
CN113447464B (zh) * 2020-11-17 2022-07-12 北京大学深圳研究生院 一种乙炔基硫盐点击反应的蛋白标记方法
KR20230112656A (ko) 2020-11-25 2023-07-27 이나뜨 파르마 에스.에이. 암의 치료
EP4271509A1 (en) 2020-12-30 2023-11-08 10X Genomics, Inc. Molecular arrays and methods for generating and using the arrays
US20220314187A1 (en) 2020-12-30 2022-10-06 10X Genomics, Inc. Methods and compositions for light-controlled surface patterning using a polymer
US20220228210A1 (en) 2020-12-30 2022-07-21 10X Genomics, Inc. Molecular array generation using photoresist
CA3203535A1 (en) 2021-01-21 2022-07-28 Gregory KAPP Systems and methods for biomolecule preparation
IL305336A (en) 2021-03-11 2023-10-01 Nautilus Subsidiary Inc Systems and methods for the preservation of biomolecules
MX2023010814A (es) 2021-03-29 2023-09-27 Illumina Inc Metodos mejorados de preparacion de genotecas.
AU2022246579A1 (en) 2021-03-30 2023-09-21 Illumina, Inc. Improved methods of isothermal complementary dna and library preparation
JP2024511760A (ja) 2021-03-31 2024-03-15 イルミナ インコーポレイテッド エラー補正のための固有分子識別子を有するトランスポゾンベースの技術を使用した指向性タグメンテーション配列決定ライブラリーの調製方法
KR20240004342A (ko) 2021-04-03 2024-01-11 암브룩스, 인코포레이티드 항-her2 항체-약물 접합체 및 이의 용도
EP4337786A1 (en) 2021-05-10 2024-03-20 Pacific Biosciences of California, Inc. Single-molecule seeding and amplification on a surface
KR20240055084A (ko) 2021-09-13 2024-04-26 라이프 테크놀로지스 코포레이션 유전자 편집 도구
WO2023055776A1 (en) 2021-09-29 2023-04-06 Michael David Austin Devices and methods for interrogating macromolecules
WO2023102336A1 (en) 2021-11-30 2023-06-08 Nautilus Subsidiary, Inc. Particle-based isolation of proteins and other analytes
CN115851347B (zh) * 2021-12-20 2023-12-08 中国科学院兰州化学物理研究所 一种界面原位润滑体系和润滑添加剂的原位制备方法
US20230210998A1 (en) * 2021-12-30 2023-07-06 Navidea Biopharmaceuticals, Inc. Methods for the conjugation of anthracyclines to carbohydrate polymeric carriers
WO2023161296A1 (en) 2022-02-22 2023-08-31 Adc Therapeutics Sa Conjugation method involving a transglutaminase at the fc region comprising a trimmed n-glycan
WO2023181081A1 (en) 2022-03-21 2023-09-28 Haskoli Islands Surface activation of silicone
WO2023227660A1 (en) 2022-05-25 2023-11-30 Innate Pharma Nectin-4 binding agents
US20240060127A1 (en) 2022-06-29 2024-02-22 10X Genomics, Inc. Methods and systems for light-controlled surface patterning using photomasks
EP4370242A1 (en) 2022-06-29 2024-05-22 10X Genomics, Inc. Compositions and methods for generating molecular arrays using oligonucleotide printing and photolithography
US20240084359A1 (en) 2022-06-29 2024-03-14 10X Genomics, Inc. Methods and compositions for patterned molecular array generation by directed bead delivery
US20240002932A1 (en) 2022-06-29 2024-01-04 10X Genomics, Inc. Click chemistry-based dna photo-ligation for manufacturing of high-resolution dna arrays
US20240117338A1 (en) 2022-06-29 2024-04-11 10X Genomics, Inc. Methods and compositions for refining feature boundaries in molecular arrays
WO2024006814A1 (en) 2022-06-29 2024-01-04 10X Genomics, Inc. Method of generating arrays using microfluidics and photolithography
WO2024006816A1 (en) 2022-06-29 2024-01-04 10X Genomics, Inc. Compositions and methods for oligonucleotide inversion on arrays
WO2024006799A1 (en) 2022-06-29 2024-01-04 10X Genomics, Inc. Covalent attachment of splint oligonucleotides for molecular array generation using ligation
WO2024006798A1 (en) 2022-06-29 2024-01-04 10X Genomics, Inc. High definition molecular array feature generation using photoresist
WO2024042489A1 (en) 2022-08-25 2024-02-29 LifeEDIT Therapeutics, Inc. Chemical modification of guide rnas with locked nucleic acid for rna guided nuclease-mediated gene editing

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3985765A (en) * 1973-05-29 1976-10-12 Miles Laboratories, Inc. Phenyl- and (substituted)-phenyl-1,2,3-triazole-alkanoic and -alkenoic acids
DE2407305C2 (de) * 1974-02-15 1984-06-28 Bayer Ag, 5090 Leverkusen Triphenyl-1,2,3-triazol-1-yl-methane, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
JP2541882B2 (ja) * 1991-05-31 1996-10-09 ケイ・アイ化成株式会社 アントラニル酸類の製造法
HUT74765A (en) * 1994-09-01 1997-02-28 Taiho Pharmaceutical Co Ltd Process for preparing 1-amino-1,2,3-triazole
US5527920A (en) * 1994-11-18 1996-06-18 Singh; Inder P. Economical manufacturing process for 1,2,3-triazoles
US5681904A (en) * 1996-04-01 1997-10-28 Minnesota Mining And Manufacturing Company Azido polymers having improved burn rate
DE19629145A1 (de) * 1996-07-19 1998-01-22 Bayer Ag Verwendung von Triphenylmethyl-1,2,3-triazolen
US6664399B1 (en) * 1999-09-02 2003-12-16 E. I. Du Pont De Nemours & Company Triazole linked carbohydrates
US7259141B2 (en) * 2001-03-30 2007-08-21 Wisconsin Alumni Research Foundation Vancomycin analogs and methods thereof
US7238719B2 (en) * 2002-02-01 2007-07-03 Meiji Seika Kaisha, Ltd. Process for producing 1,2,3-Triazole compounds
DK2226316T3 (en) * 2002-05-30 2016-04-11 Scripps Research Inst Copper catalyzed ligation of azides and acetylenes
WO2005103705A2 (en) * 2004-04-16 2005-11-03 University Of South Carolina Chemoselective fluorogenic molecular linkers and methods of their preparation and use
PL1828148T3 (pl) * 2004-12-13 2010-08-31 Leo Pharma As Triazol podstawiony związkami aminobenzofenonu

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