DK2563753T3 - Kondenseret cyclooctynforbindelser og deres anvendelse i metal-fri click-reaktioner - Google Patents

Kondenseret cyclooctynforbindelser og deres anvendelse i metal-fri click-reaktioner Download PDF

Info

Publication number
DK2563753T3
DK2563753T3 DK11720197.0T DK11720197T DK2563753T3 DK 2563753 T3 DK2563753 T3 DK 2563753T3 DK 11720197 T DK11720197 T DK 11720197T DK 2563753 T3 DK2563753 T3 DK 2563753T3
Authority
DK
Denmark
Prior art keywords
groups
hetero
group
alkyl
compound
Prior art date
Application number
DK11720197.0T
Other languages
English (en)
Other versions
DK2563753T6 (da
Inventor
Delft Floris Louis Van
Floris Petrus Johannes Theodorus Rutjes
Frederik Jan Dommerholt
Original Assignee
Synaffix Bv
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Synaffix Bv filed Critical Synaffix Bv
Application granted granted Critical
Publication of DK2563753T3 publication Critical patent/DK2563753T3/da
Publication of DK2563753T6 publication Critical patent/DK2563753T6/da

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/16—Alcohols containing rings other than six-membered aromatic rings containing rings with more than six ring members
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
    • A61K49/0052—Small organic molecules
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/58—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of halogen, e.g. by hydrogenolysis, splitting-off
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/531—Production of immunochemical test materials
    • G01N33/532—Production of labelled immunochemicals
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/585—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with a particulate label, e.g. coloured latex
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
    • G01N33/6848—Methods of protein analysis involving mass spectrometry
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks

Claims (17)

1. Forbindelse med formlen (Ila):
(Ha) hvor: p er 0 eller 1; R3 er udvalgt fra gruppen bestående af [(L)p-Q], hydrogen, halogen, Ci - C24 alkylgrupper, C6 - C24 (hetero)arylgrupper, C7 - C24 alkyl(hetero)arylgrupper og C7 - C24 (hetero)arylalkylgrupper, hvor alkylgrupper eventuelt afbrydes af et eller flere heteroatomer, der er udvalgt fra gruppen bestående af O, N og S, hvor alkylgrupperne, (hetero)arylgrupperne, alkyl(hetero)arylgrupperne og (hetero)arylalkylgrupperne uafhængigt eventuelt er substitueret med en eller flere substituenter, der uafhængigt er udvalgt fra gruppen bestående af C1 -C12 alkylgrupper, C2 - C12 alkenylgrupper, C2 - C12 alkynylgrupper, C3 - C12 cycloalkylgrupper, C1 - C12 alkoxygrupper, C2 - C12 alkenyloxygrupper, C2 -C12 alkynyloxygrupper, C3 - C12 cycloalkyloxygrupper, halogener, aminogrup-per, oxogrupper og silylgrupper, hvor alkylgrupperne, alkenylgrupperne, al-kynylgrupperne, cycloalkylgrupperne, alkoxygrupperne, alkenyloxygrupperne, alkynyloxygrupperne og cycloalkyloxygrupperne eventuelt er substituerede, alkylgrupperne, alkoxygrupperne, cycloalkylgrupperne og cycloalkoxygrup-perne eventuelt afbrydes af et eller flere heteroatomer, der er udvalgt fra gruppen bestående af O, N og S, hvor silylgrupperne repræsenteres af formlen (R4)3Si-, hvor R4 uafhængigt er udvalgt fra gruppen bestående af C1 - C12 alkylgrupper, C2 - C12 alkenylgrupper, C2 - C12 alkynylgrupper, C3 - C12 cycloalkylgrupper, C1 - C12 alkoxygrupper, C2 - C12 alkenyloxygrupper, C2 - C12 alkynyloxygrupper og C3 - C12 cycloalkyloxygrupper, hvor alkylgrupperne, alkenylgrupperne, alkynylgrupperne, cycloalkylgrupperne, alkoxygrupperne, alkenyloxygrupperne, alkynyloxygrupperne og cycloalkyloxygrupperne eventuelt er substituerede, alkylgrupperne, alkoxygrupperne, cycloalkylgrupperne og cycloalkoxygrupperne eventuelt afbrydes af et eller flere heteroatomer, der er udvalgt fra gruppen bestående af O, N og S, L er en forbindelsesgruppe, der er udvalgt blandt lineære eller forgrenede Ci - C24 alkylenegrupper, C2 - C24 alkenylengrupper, C2 - C24 alkynylengrupper, C3 - C24 cycloalkylengrupper, C5 - C24 cycloalkenylengrupper, C8 - C24 cy-cloalkynylengrupper, C7 - C24 alkyl(hetero)arylengrupper, C7 - C24 (hete-ro)arylalkylengrupper, C8 - C24 (hetero)arylalkenylengrupper, C9 - C24 (hete-ro)arylalkynylengrupper, alkylengrupperne, alkenylengrupperne, alkynylen-grupperne, cycloalkylengrupperne, cycloalkenylengrupperne, cycloalkynylen-grupperne, alkyl(hetero)arylengrupperne, (hetero)arylalkylengrupperne, (he-tero)arylalkenylengrupperne og (hetero)arylalkynylengrupperne eventuelt er substitueret med en eller flere substituenter, der uafhængigt er udvalgt fra gruppen bestående af C1 - C-|2 alkylgrupper, C2 - C-|2 alkenylgrupper, C2 - Ci2 alkynylgrupper, C3 - Ci2 cycloalkylgrupper, C5 - C12 cycloalkenylgrupper, C8 -C-|2 cycloalkynylgrupper, C1 - C-|2 alkoxygrupper, C2 - Ci2 alkenyloxygrupper, C2 - C-|2 alkynyloxygrupper, C3 - Ci2 cycloalkyloxygrupper, halogener, amino-grupper, oxo- og silylgrupper, hvor silylgrupperne kan repræsenteres af formlen (R4)3Si-, hvor R4 er defineret som ovenfor; Q er en funktionel gruppe, der er udvalgt fra gruppen bestående af hydrogen, halogen, R6, -CH=C(R6)2, -C=CR6, -[C(R6)2C(R6)20]q-R6, hvor q ligger mellem 1 til 200, -CN, -N3, -NCX, -XCN, -XR6, -N(R6)2, -+N(R6)3, -C(X)N(R6)2, -C(R6)2XR6, -C(X)R6, -C(X)XR6, -S(0)R6, -S(0)2R6, -S(0)0R6, -S(0)20R6, -S(0)N(R6)2, -S(0)2N(R6)2, -0S(0)R6, -0S(0)2R6, -0S(0)0R6, -0S(0)20R6, -P(0)(R6)(0R6), -P(0)(0R6)2, -0P(0)(0R6)2, -Si(R6)3, -XC(X)R6, -XC(X)XR6, -XC(X)N(R6)2, -N(R6)C(X)R6, -N(R6)C(X)XR6 og-N(R6)C(X)N(R6)2, hvor X er oxygen eller sulphur, og hvor R6 uafhængigt er udvalgt fra gruppen bestående af hydrogen, halogen, C1 - C24 alkylgrupper, C6 - C24 (hetero)arylgrupper, C7 - C24 alkyl(hetero)arylgrupper og C7 - C24 (hetero)arylalkylgrupper; og R1 uafhængigt er udvalgt fra gruppen bestående af hydrogen, C1 - C24 alkylgrupper, C6 - C24 (hetero)arylgrupper, C7 - C24 alkyl(hetero)arylgrupper og C7 - C24 (hetero)arylalkylgrupper.
2. Forbindelse ifølge krav 1, hvor p er 1, og L er CH2.
3. Forbindelse ifølge krav 1 eller krav 2, hvor Q er udvalgt fra gruppen bestående af -OR6, -N(R6)2, -+N(R6)3, -C(0)N(R6)2, -C(0)0R6, -0C(0)R6, -0C(0)0R6, -0C(0)N(R6)2, -N(R6)C(0)R6, -N(R6)C(0)0R6 og -N(R6)C(0)N(R6)2, hvor R6 er som defineret i krav 1.
4. Forbindelse ifølge et hvilket som helst af kravene 1 til 3, hvor Q er -OH.
5. Forbindelse ifølge et hvilket som helst af kravene 1 til 4, hvor Ri er hydrogen.
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor R3 er hydrogen eller [(L)p-Q].
7. Forbindelse ifølge krav 2, hvor Q er -OH, R1 er hydrogen, og R3 er hydrogen eller [(L)p-Q].
8. Forbindelse ifølge krav 7, hvor forbindelsen har formlen (exo-lla.2) eller {endo- lla.2):
(exo -Ila.2) (etido -IIa.2)
9. Konjugat, hvor en forbindelse ifølge et hvilket som helst af kravene 1 - 8 er konjugeret til en markering via en funktionsgruppe Q.
10. Konjugat ifølge krav 9, hvor funktionsgruppen Q er forbundet til markeringen via en forbindelsesenhed af strukturen Q-S-Q, hvor Q er som defineret i krav 1, og hvor S er udvalgt fra gruppen bestående af lineære eller forgrenede CrC20o alkylengrupper, C2-C20o alkenylengrupper, C2-C20o alkynylen-grupper, C3-C20o cycloalkylengrupper, C5-C20o cycloalkenylengrupper, C8-C20o cycloalkynylengrupper, C7-C20o alkylarylengrupper, C7-C20o arylalkylengrup-per, Cs-C20o arylalkenylengrupper, C9-C20o arylalkynylengrupper, hvor eventuelt alkylengrupperne, alkenylengrupperne, alkynylengrupperne, cycloalky- lengrupperne, cycloalkenylengrupperne, cycloalkynylengrupperne, alkylary-lengrupperne, arylalkylengrupperne, arylalkenylengrupperne og arylalkyny-lengrupperne er substituerede, og hvor grupperne eventuelt afbrydes af et eller flere heteroatomer, hvor heteroatomerne er udvalgt fra gruppen bestående af O, S og NR6, hvor R6 er som defineret i krav 1.
11. Konjugat ifølge krav 9 eller krav 10, hvor i forbindelsen ifølge et hvilket som helst af kravene 1 - 8, p er 1, L er CH2, R1 er H, og R3 er H.
12. Konjugat ifølge et hvilket som helst af kravene 9-11, hvor markeringen er udvalgt blandt gruppen, som omfatter fluorophorer, biotin, polyethylengly-col-kæder, polypropylenglycol-kæder, blandede polyethy-len/polypropylenglycol-kæder, radioaktive isotoper, steroider, farmaceutiske forbindelser, lipider, peptider, glycaner, nucleotider og peptidtags.
13. Fremgangsmåde til fremstilling af en forbindelse ifølge et hvilket som helst af kravene 1 - 8, hvor fremgangsmåden omfatter de følgende trin: (a) Cyclopropanation af en cyclooctadien af formlen (Vila):
(Vila) hvor: R1 uafhængigt er udvalgt fra gruppen bestående af hydrogen, Ci - C24 alkylgrupper, C6 - C24 (hetero)arylgrupper, C7 - C24 al-kyl(hetero)arylgrupper og C7 - C24 (hetero)arylalkylgrupper; for at danne en bicyclisk cyclooctenforbindelse, (b) Bromering af den opnåede bicykliske cyclooctenforbindelse for at danne bicyclisk cyclooctanforbindelse, og (c) Dehydrobromering af den opnåede bicycliske cyclooctanforbindelse for at danne en forbindelse ifølge et hvilket som helst af kravene 1 - 8.
14. Fremgangsmåde til modificering af et målmolekyle, hvor et konjugat ifølge et hvilket som helst af kravene 9-12 reageres med en forbindelse omfattende en 1,3-dipol eller en 1,3-(hetero)dien.
15. Fremgangsmåde ifølge krav 14, hvor forbindelsen, som omfatter en 1,3-dipol, er an azid-omfattende forbindelse, en nitron-omfattende forbindelse eller en nitriloxid-omfattende forbindelse.
16. Anvendelse af et konjugat ifølge et hvilket som helst af kravene 9 - 12 til bioorthogonal markering, billeddannelse eller modificering af et målmolekyle.
17. Sammensætning, omfattende et konjugat ifølge et hvilket som helst af kravene 9-12, yderligere omfattende en farmaceutisk acceptabel bærer.
DK11720197.0T 2010-04-27 2011-04-26 Kondenserede cyclooctynforbindelser og deres anvendelse i metalfri click-reaktioner DK2563753T6 (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US32830610P 2010-04-27 2010-04-27
EP10161192 2010-04-27
PCT/NL2011/050280 WO2011136645A1 (en) 2010-04-27 2011-04-26 Fused cyclooctyne compounds and their use in metal-free click reactions

Publications (2)

Publication Number Publication Date
DK2563753T3 true DK2563753T3 (da) 2014-12-01
DK2563753T6 DK2563753T6 (da) 2016-04-04

Family

ID=42668639

Family Applications (1)

Application Number Title Priority Date Filing Date
DK11720197.0T DK2563753T6 (da) 2010-04-27 2011-04-26 Kondenserede cyclooctynforbindelser og deres anvendelse i metalfri click-reaktioner

Country Status (8)

Country Link
US (5) US8859629B2 (da)
EP (3) EP2563753B9 (da)
JP (1) JP5920936B2 (da)
CN (2) CN107235828A (da)
DK (1) DK2563753T6 (da)
ES (1) ES2527536T7 (da)
PL (1) PL2563753T6 (da)
WO (1) WO2011136645A1 (da)

Families Citing this family (110)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7855279B2 (en) 2005-09-27 2010-12-21 Amunix Operating, Inc. Unstructured recombinant polymers and uses thereof
CN102348715B (zh) 2009-02-03 2017-12-08 阿穆尼克斯运营公司 延伸重组多肽和包含该延伸重组多肽的组合物
EP2563753B9 (en) * 2010-04-27 2016-07-06 SynAffix B.V. Fused cyclooctyne compounds and their use in metal-free click reactions
US9517257B2 (en) 2010-08-10 2016-12-13 Ecole Polytechnique Federale De Lausanne (Epfl) Erythrocyte-binding therapeutics
CN108117586A (zh) 2010-08-10 2018-06-05 洛桑聚合联合学院 红细胞结合性治疗剂
CA2826041C (en) * 2011-02-03 2020-07-07 Embl Unnatural amino acids comprising a cyclooctynyl or trans-cyclooctenyl analog group and uses thereof
US20130066063A1 (en) * 2011-09-09 2013-03-14 John Cooke Hodges Bicyclo[6.1.0]non-4-yne regents for chemical modification of oligonucleotides
JP2013151468A (ja) * 2011-11-30 2013-08-08 Agilent Technologies Inc オリゴマーの合成及び精製の新規方法
US9717803B2 (en) 2011-12-23 2017-08-01 Innate Pharma Enzymatic conjugation of polypeptides
US20130178600A1 (en) * 2012-01-09 2013-07-11 Intezyne Technologies, Inc. Poly(ethylene glycol) derivatives for click chemistry
CN117462693A (zh) 2012-02-27 2024-01-30 阿穆尼克斯运营公司 Xten缀合组合物和制造其的方法
WO2013171485A1 (en) 2012-05-18 2013-11-21 Medical Research Council Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase.
WO2013181697A1 (en) * 2012-06-05 2013-12-12 The University Of Melbourne Bicyclo[6.1.0]non-4-yne compounds suitable for use as linkers in biological applications
WO2013188635A2 (en) * 2012-06-14 2013-12-19 The Trustees Of The University Of Pennsylvania Novel methods of identifying proteins via n-terminal tagging and selective pull-down
EP2872894B1 (en) 2012-07-13 2019-04-17 Innate Pharma Screening of conjugated antibodies
EP2888238A4 (en) * 2012-08-21 2016-01-27 Academia Sinica BENZOCYCLO-OCTYNE COMPOUNDS AND USES THEREOF
US9670521B2 (en) 2012-09-24 2017-06-06 Medimmune Limited Amino acid derivatives
CN110201186A (zh) 2012-10-23 2019-09-06 西纳福克斯股份有限公司 经修饰的抗体、抗体-缀合物及其制备方法
US10036010B2 (en) 2012-11-09 2018-07-31 Innate Pharma Recognition tags for TGase-mediated conjugation
GB201300707D0 (en) * 2013-01-15 2013-02-27 Novartis Ag Compounds and processes
EP2961434A2 (en) 2013-02-28 2016-01-06 ImmunoGen, Inc. Conjugates comprising cell-binding agents and cytotoxic agents
JP6423804B2 (ja) 2013-02-28 2018-11-14 イミュノジェン・インコーポレーテッド 細胞結合剤及び細胞毒性剤を含む複合体
WO2014140300A1 (en) 2013-03-15 2014-09-18 Innate Pharma Solid phase tgase-mediated conjugation of antibodies
LT2991683T (lt) 2013-05-02 2019-12-27 Glykos Finland Oy Glikoproteino arba glikano konjugatai su toksine medžiaga
WO2014189370A1 (en) 2013-05-24 2014-11-27 Stichting Katholieke Universiteit Substituted azadibenzocyclooctyne compounds and their use in metal-free click reactions
WO2014194030A2 (en) 2013-05-31 2014-12-04 Immunogen, Inc. Conjugates comprising cell-binding agents and cytotoxic agents
US10071169B2 (en) 2013-06-20 2018-09-11 Innate Pharma Enzymatic conjugation of polypeptides
AU2014283185B2 (en) * 2013-06-21 2019-05-02 Innate Pharma Enzymatic conjugation of polypeptides
ES2756526T3 (es) * 2013-07-11 2020-04-27 Novartis Ag Modificaciones de proteínas quimioenzimáticas específicas para lisina utilizando transglutaminasa microbiana
CN104292454B (zh) * 2013-07-17 2017-12-01 北京键凯科技股份有限公司 聚乙二醇‑环辛炔衍生物
WO2015007771A1 (en) 2013-07-18 2015-01-22 Stichting Katholieke Universiteit, More Particularly Radboud Universiteit Nijmegen Polymer suitable for use in cell culture
EP2826493A1 (en) 2013-07-18 2015-01-21 Stichting Katholieke Universiteit, Radboud Universiteit Nijmegen Polymer suitable for use in cell culture
US9987373B2 (en) 2013-10-14 2018-06-05 Synaffix B.V. Modified glycoprotein, protein-conjugate and process for the preparation thereof
CN105829543B (zh) 2013-10-14 2021-06-01 西纳福克斯股份有限公司 糖基改造的抗体、抗体-缀合物及其制备方法
EP3057618B1 (en) 2013-10-14 2022-12-14 SynAffix B.V. Glycoengineered antibody, antibody-conjugate and methods for their preparation
JP6564369B2 (ja) 2013-12-09 2019-08-21 デュレクト コーポレイション 薬学的活性剤複合体、ポリマー複合体、ならびにこれらを伴う組成物及び方法
JP2017505770A (ja) 2014-01-24 2017-02-23 シンアフィックス ビー．ブイ． （ヘテロ）アリール１，３−双極子化合物と（ヘテロ）シクロアルキンとの環化付加のためのプロセス
US10953101B2 (en) 2014-02-21 2021-03-23 École Polytechnique Fédérale De Lausanne (Epfl) Glycotargeting therapeutics
US10946079B2 (en) 2014-02-21 2021-03-16 Ecole Polytechnique Federale De Lausanne Glycotargeting therapeutics
JP6744227B2 (ja) 2014-02-21 2020-08-19 エコール・ポリテクニーク・フェデラル・ドゥ・ローザンヌ（ウペエフエル）Ｅｃｏｌｅ Ｐｏｌｙｔｅｃｈｎｉｑｕｅ Ｆｅｄｅｒａｌｅ ｄｅ Ｌａｕｓａｎｎｅ （ＥＰＦＬ） 糖標的化治療剤
US10046056B2 (en) 2014-02-21 2018-08-14 École Polytechnique Fédérale De Lausanne (Epfl) Glycotargeting therapeutics
GB2528227A (en) 2014-03-14 2016-01-20 Medical Res Council Cyclopropene amino acids and methods
WO2015157446A1 (en) 2014-04-08 2015-10-15 University Of Georgia Research Foundation Inc. Site-specific antibody-drug glycoconjugates and methods
US10588980B2 (en) 2014-06-23 2020-03-17 Novartis Ag Fatty acids and their use in conjugation to biomolecules
EP2974744A1 (en) 2014-07-16 2016-01-20 Stichting Katholieke Universiteit Strain-promoted oxidation controlled cycloaddition with high reaction rate
CN105510591B (zh) * 2014-09-22 2019-02-12 程永升 一种利用抗体修饰免疫pcr反应的检测试剂盒及检测方法
JP6440250B2 (ja) * 2014-10-09 2018-12-19 国立大学法人富山大学 チオアミド誘導体
US9803201B2 (en) 2015-03-17 2017-10-31 Arrowhead Pharmaceuticals, Inc. Disulfide-containing alkyne linking agents
US10683288B2 (en) 2015-07-24 2020-06-16 The Trustees Of Columbia University In The City Of New York Epothilone B and dictyostatin analogs, their preparation and use
KR102368068B1 (ko) 2015-08-24 2022-02-25 삼성전자주식회사 반도체 소자 제조용 조성물 및 이를 이용하는 반도체 소자의 제조 방법
AU2016341208A1 (en) * 2015-10-20 2018-05-10 Sorrento Therapeutics, Inc. Intracellular delivery compounds
EP3407917A1 (en) 2016-01-27 2018-12-05 Sutro Biopharma, Inc. Anti-cd74 antibody conjugates, compositions comprising anti-cd74 antibody conjugates and methods of using anti-cd74 antibody conjugates
WO2017137457A1 (en) 2016-02-08 2017-08-17 Synaffix B.V. Antibody-conjugates with improved therapeutic index for targeting cd30 tumours and method for improving therapeutic index of antibody-conjugates
CN109069658B (zh) 2016-02-08 2022-10-14 西纳福克斯股份有限公司 用于靶向her2肿瘤的具有改善的治疗指数的抗体-缀合物以及用于改善抗体-缀合物的治疗指数的方法
EP3413920A1 (en) 2016-02-08 2018-12-19 Synaffix B.V. Bioconjugates containing sulfamide linkers for use in treatment
EP3413922A1 (en) 2016-02-08 2018-12-19 SynAffix B.V. Improved sulfamide linkers for use in bioconjugates
WO2017137458A1 (en) 2016-02-08 2017-08-17 Synaffix B.V. Antibody-conjugates with improved therapeutic index for targeting cd30 tumours and method for improving therapeutic index of antibody-conjugates
WO2017147542A2 (en) 2016-02-26 2017-08-31 Regeneron Pharmaceuticals, Inc. Optimized transglutaminase site-specific antibody conjugation
EP3453758A4 (en) 2016-05-02 2019-12-04 Ajinomoto Co., Inc. FC PROTEIN WITH AZID GROUP
TWI673363B (zh) 2016-12-29 2019-10-01 財團法人生物技術開發中心 製備醣蛋白-藥物共軛物之方法
EP3357903B1 (en) 2017-02-06 2020-11-04 Stichting Katholieke Universiteit Method for a continuous production of a z-cyclooctene
JP7216006B2 (ja) 2017-03-22 2023-01-31 ジェネンテック， インコーポレイテッド ヒドロゲル架橋ヒアルロン酸プロドラッグ組成物及び方法
JOP20190245A1 (ar) 2017-04-20 2019-10-15 Novartis Ag أنظمة توصيل إطلاق مستدام تتضمن روابط بلا أثر لنقطة الربط
WO2018232176A1 (en) * 2017-06-16 2018-12-20 The University Of Chicago Compositions and methods for inducing immune tolerance
EP3658588A1 (en) 2017-07-26 2020-06-03 Sutro Biopharma, Inc. Methods of using anti-cd74 antibodies and antibody conjugates in treatment of t-cell lymphoma
US10596270B2 (en) 2017-09-18 2020-03-24 Sutro Biopharma, Inc. Anti-folate receptor antibody conjugates, compositions comprising anti-folate receptor antibody conjugates, and methods of making and using anti-folate receptor antibody conjugates
JP7295571B2 (ja) * 2018-02-05 2023-06-21 国立大学法人 宮崎大学 細胞標識剤及び細胞標識キット
CN110117268B (zh) * 2018-02-06 2020-10-16 华中科技大学 一种甘草素探针及其制备方法和应用
CA3103227A1 (en) * 2018-06-14 2019-12-19 Mochida Pharmaceutical Co., Ltd. Novel crosslinked alginic acid
US20210402002A1 (en) 2018-06-19 2021-12-30 Glykos Biomedical Oy Conjugate
JP2021529163A (ja) 2018-06-29 2021-10-28 グリコス バイオメディカル オーワイ コンジュゲート
KR20210081324A (ko) 2018-08-02 2021-07-01 다인 세라퓨틱스, 인크. 근육 표적화 복합체 및 안면견갑상완 근육 이영양증을 치료하기 위한 그의 용도
US11911484B2 (en) 2018-08-02 2024-02-27 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating myotonic dystrophy
US11168141B2 (en) 2018-08-02 2021-11-09 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating dystrophinopathies
US20210308273A1 (en) 2018-08-02 2021-10-07 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating dystrophinopathies
JP2022500454A (ja) 2018-09-17 2022-01-04 ストロ バイオファーマ インコーポレーテッド 抗葉酸受容体抗体コンジュゲートによる併用療法
FR3086290B1 (fr) 2018-09-25 2020-11-27 Univ Bordeaux Complexes de cycloheptyne-cobalt carbonyles et leurs applications en bioconjugaison
AR116566A1 (es) 2018-10-03 2021-05-19 Novartis Ag Administración sostenida de polipéptidos similares a la angiopoyetina 3
US20220362394A1 (en) 2019-05-03 2022-11-17 Sutro Biopharma, Inc. Anti-bcma antibody conjugates
EP3962946A1 (en) 2019-05-03 2022-03-09 Celgene Corporation Anti-bcma antibody conjugate, compositions comprising the same, and methods of making and using the same
CN114269749A (zh) 2019-06-10 2022-04-01 苏特罗生物制药公司 5H-吡咯并[3,2-d]嘧啶-2,4-二氨基化合物及其抗体偶联物
KR102133823B1 (ko) * 2019-06-12 2020-07-15 한국원자력연구원 퀴논 화합물을 이용한 방사성 원소의 표지방법, 방사성 표지화합물 및 이를 포함하는 방사성 원소 표지 키트
CN114746420A (zh) 2019-06-17 2022-07-12 苏特罗生物制药公司 用于癌症治疗和诊断的作为Toll样受体（TLR）7/8激动剂的1-(4-(氨基甲基)苄基)-2-丁基-2H-吡唑并[3,4-c]喹啉-4-胺衍生物及相关化合物以及其抗体药物偶联物
CA3144606A1 (en) * 2019-06-28 2020-12-30 Mochida Pharmaceutical Co., Ltd. Transplantation device using chemically crosslinked alginic acid
US20230038373A1 (en) 2019-12-18 2023-02-09 Glykos Biomedical Oy Stabile conjugate
US11786605B2 (en) 2020-01-09 2023-10-17 Mersana Therapeutics, Inc. Site specific antibody-drug conjugates with peptide-containing linkers
KR102270784B1 (ko) * 2020-01-13 2021-06-28 경희대학교 산학협력단 새로운 덱스트란 고분자 청색 형광체
US20230095053A1 (en) 2020-03-03 2023-03-30 Sutro Biopharma, Inc. Antibodies comprising site-specific glutamine tags, methods of their preparation and methods of their use
KR20230004682A (ko) 2020-04-22 2023-01-06 머크 샤프 앤드 돔 엘엘씨 인터류킨-2 수용체 베타 감마c 이량체에 대해 편향되고 비펩티드성 수용성 중합체에 접합된 인간 인터류킨-2 접합체
WO2022103983A2 (en) 2020-11-11 2022-05-19 Sutro Biopharma, Inc. Fluorenylmethyloxycarbonyl and fluorenylmethylaminocarbonyl compounds, protein conjugates thereof, and methods for their use
AR125490A1 (es) 2021-04-30 2023-07-19 Celgene Corp Terapias de combinación que utilizan un anticuerpo anti-bcma conjugado a fármaco (adc) en combinación con un inhibidor de gamma secretasa (gsi)
US11377424B1 (en) 2021-05-27 2022-07-05 Massachusetts Institute Of Technology Cyclooctynes for click chemistry
WO2022250679A1 (en) * 2021-05-27 2022-12-01 Massachusetts Institute Of Technology Cyclooctynes for click chemistry
TW202320857A (zh) 2021-07-06 2023-06-01 美商普方生物製藥美國公司 連接子、藥物連接子及其結合物及其使用方法
US11638761B2 (en) 2021-07-09 2023-05-02 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating Facioscapulohumeral muscular dystrophy
US11672872B2 (en) 2021-07-09 2023-06-13 Dyne Therapeutics, Inc. Anti-transferrin receptor antibody and uses thereof
US11633498B2 (en) 2021-07-09 2023-04-25 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating myotonic dystrophy
US11771776B2 (en) 2021-07-09 2023-10-03 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating dystrophinopathies
US11969475B2 (en) 2021-07-09 2024-04-30 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating facioscapulohumeral muscular dystrophy
KR20240024235A (ko) 2021-07-29 2024-02-23 노보코덱스 바이오파마슈티컬즈 컴퍼니 리미티드 비천연 아미노산, 및 이의 용도, 이를 함유하는 재조합 단백질, 및 재조합 단백질 컨주게이트
WO2023004687A1 (zh) 2021-07-29 2023-02-02 浙江新码生物医药有限公司 一种非天然氨基酸及其应用、包含其的重组蛋白以及重组蛋白偶联物
CN113548984B (zh) * 2021-07-29 2023-08-11 浙江新码生物医药有限公司 一种非天然氨基酸及其应用、包含其的重组蛋白以及重组蛋白偶联物
CN113698468B (zh) 2021-09-01 2022-10-11 浙江新码生物医药有限公司 人白细胞介素2-聚乙二醇偶联物及其应用
CN114085130B (zh) * 2021-12-08 2022-08-30 西安康福诺生物科技有限公司 ((1r,8s,9s,z)-双环[6.1.0]非-4-烯-9-基)甲醇的合成方法
US11931421B2 (en) 2022-04-15 2024-03-19 Dyne Therapeutics, Inc. Muscle targeting complexes and formulations for treating myotonic dystrophy
US20240091365A1 (en) 2022-06-27 2024-03-21 Sutro Biopharma, Inc. Beta-glucuronide linker-payloads, protein conjugates thereof, and methods thereof
US20240058465A1 (en) 2022-06-30 2024-02-22 Sutro Biopharma, Inc. Anti-ror1 antibody conjugates, compositions comprising anti ror1 antibody conjugates, and methods of making and using anti-ror1 antibody conjugates
WO2024015229A1 (en) 2022-07-15 2024-01-18 Sutro Biopharma, Inc. Protease/enzyme cleavable linker-payloads and protein conjugates
WO2024044780A1 (en) 2022-08-26 2024-02-29 Sutro Biopharma, Inc. Interleukin-18 variants and uses thereof
EP4344707A1 (en) 2022-09-29 2024-04-03 Emergence Therapeutics AG New anti-nectin-4 antibody drug conjugates

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8431558B2 (en) 2004-11-01 2013-04-30 The Regents Of The University Of California Compositions and methods for modification of biomolecules
US8137925B2 (en) * 2007-11-09 2012-03-20 Massachusetts Institute Of Technology Methods and compositions for protein labeling using lipoic acid ligases
CN101925366B (zh) 2007-11-21 2015-02-04 乔治亚大学研究基金公司 炔烃以及炔烃与1,3-偶极-官能化合物反应的方法
EP2563753B9 (en) * 2010-04-27 2016-07-06 SynAffix B.V. Fused cyclooctyne compounds and their use in metal-free click reactions
CA2826041C (en) * 2011-02-03 2020-07-07 Embl Unnatural amino acids comprising a cyclooctynyl or trans-cyclooctenyl analog group and uses thereof

Also Published As

Publication number Publication date
JP2013525425A (ja) 2013-06-20
US20150125892A1 (en) 2015-05-07
EP2563753B1 (en) 2014-11-05
EP3604264A1 (en) 2020-02-05
WO2011136645A1 (en) 2011-11-03
CN103153927A (zh) 2013-06-12
US20230102685A1 (en) 2023-03-30
CN107235828A (zh) 2017-10-10
US20130137763A1 (en) 2013-05-30
EP2894142B1 (en) 2019-06-12
DK2563753T6 (da) 2016-04-04
PL2563753T3 (pl) 2015-04-30
ES2527536T3 (es) 2015-01-26
PL2563753T6 (pl) 2016-05-31
JP5920936B2 (ja) 2016-05-18
CN103153927B (zh) 2017-02-15
EP2563753A1 (en) 2013-03-06
US9222940B2 (en) 2015-12-29
ES2527536T7 (es) 2016-03-08
US20200048174A1 (en) 2020-02-13
EP2563753B3 (en) 2016-01-06
US11358921B2 (en) 2022-06-14
US8859629B2 (en) 2014-10-14
EP2894142A1 (en) 2015-07-15
US10239807B2 (en) 2019-03-26
EP2563753B9 (en) 2016-07-06
US20160214917A1 (en) 2016-07-28

Similar Documents

Publication Publication Date Title
DK2563753T3 (da) Kondenseret cyclooctynforbindelser og deres anvendelse i metal-fri click-reaktioner
Qi et al. Highly efficient aggregation-induced red-emissive organic thermally activated delayed fluorescence materials with prolonged fluorescence lifetime for time-resolved luminescence bioimaging
Debets et al. Azide: a unique dipole for metal‐free bioorthogonal ligations
EP3004062B1 (en) Substituted azadibenzocyclooctyne compounds and their use in metal-free click reactions
AU2011235868A1 (en) Single isomeric conjugates of rhodamine dyes
CN111393430B (zh) 一种百部生物碱类似物近红外荧光探针及其制备方法
US20130190500A1 (en) Process to prepare 6-chloro-3-amino-2-(2-hydroxypropyl)-1-azanaphthalene
Chen et al. An efficient and versatile approach for the preparation of a rhodamine B ester bioprobe library
US8541604B2 (en) Process for the functionalization of biological molecules
US20230331652A1 (en) Trans-cyclooctenes with high reactivity and favorable physiochemical properties
CN112266388B (zh) 一类具有标记功能用于超分辨成像的亚硝基笼化罗丹明衍生物及应用
Avenoza et al. α-Methylserinals as an access to α-methyl-β-hydroxyamino acids: application in the synthesis of all stereoisomers of α-methylthreonine
CN112920095A (zh) 新型聚集诱导发光内质网荧光探针及其制备方法与应用
EP2974744A1 (en) Strain-promoted oxidation controlled cycloaddition with high reaction rate
Forshaw Synthesis and reactivity of novel biaryl strained alkynes
RU2614247C2 (ru) СПОСОБ ПОЛУЧЕНИЯ ЭНАНТИОМЕРНО ЧИСТЫХ (S)-АМИНОКИСЛОТ НА ОСНОВЕ КОМПЛЕКСА [(S)-BPB-GLy]Ni(II), НАПРЯМУЮ СВЯЗАННЫХ С ФУЛЛЕРЕНОВЫМ ЯДРОМ ЧЕРЕЗ α-УГЛЕРОДНЫЙ АТОМ, В ФОРМЕ ХИРАЛЬНЫХ (f,tA) И (f,tC) 1,4-АДДУКТОВ [60]ФУЛЛЕРЕНА
Sheng et al. No-wash live cell imaging with a photoswitchable near-infrared hCRBPII protein-fluorophore tag
Pirkle et al. Synthesis of. gamma.-spiro lactones and. gamma.-spiro lactams. Diels-Alder adducts based on a 9, 10-dihydro-9, 10-ethanoanthracene structure
FR3086290A1 (fr) Complexes de cycloheptyne-cobalt carbonyles et leurs applications en bioconjugaison
Baskin Development of copper-free click chemistry and application to imaging glycans in living systems