# US 2015/0147752 A1 · New iridium-based complexes for ecl

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- Number: US 2015/0147752 A1
- Document ID: US20150147752A1
- Status: Published application
- Kind: A1
- Application number: 14/610,244
- Filed: 2015-01-30
- Published: 2015-05-28
- Earliest claimed: 2012-08-02
- Assignees: Roche Diagnostics Operations, Inc.
- Applicants: Roche Diagnostics Operations, Inc.
- Inventors: Frank Bergmann; Robert Cysewski; Luisa de Cola; Sebastian Dziadek; Jesus Miguel Fernandez Hernandez; Hans-Peter Josel; Elena Longhi; Christoph Seidel
- Web page: https://patentgrep.com/patent/US20150147752A1

## CPC

- C07F 15/0033: {Iridium compounds}
- C09K 11/06: containing organic luminescent materials
- G01N 33/582: {with fluorescent label}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/14: Macromolecular compounds
- C09K 2211/1416: Condensed systems
- C09K 2211/1425: Non-condensed systems
- C09K 2211/1441: Heterocyclic
- C09K 2211/1466: containing nitrogen as the only heteroatom
- C09K 2211/1475: containing nitrogen and oxygen as heteroatoms
- C09K 2211/1491: containing other combinations of heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- G01N 2458/30: Electrochemically active labels
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

The present invention relates to novel iridium-based Ir(III) luminescent complexes, conjugates comprising these complexes as a label and their application, e.g. in the electrochemiluminescence based detection of an analyte.

## Claims

### Claim 1

An iridium-based chemiluminescent compound of Formula I
wherein X and Y are C—R18 and C—R19, respectively, or wherein X is N and Y is C—R19, or wherein Y is N and X is C—R18,
wherein each R1-R19 independently is hydrogen, halide, cyano- or nitro-group, amino, substituted amino, alkylamino, substituted alkylamino, arylamino, substituted arylamino, alkylammonium, substituted alkylammonium, carboxy, carboxylate, carboxylic acid ester, carbamoyl, hydroxy, substituted or unsubstituted alkyloxy, substituted or unsubstituted aryloxy, sulfanyl, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, sulfo, sulfino, sulfeno, sulfonate, sulfinate, sulfenate, sulfamoyl, sulfoxide, phosphono, hydroxyphosphinoyl, hydroxy-alkyl-phosphinoyl, phosphonate, phosphinate or R20, wherein R20 is aryl, substituted aryl, alkyl, substituted alky, branched alkyl, substituted branched alkyl, arylalkyl, substituted arylalkyl, alkylaryl, substituted alkylaryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, amino-alkyl, substituted amino-alkyl, amino-alkoxy, substituted amino-alkoxy, amino-aryl, substituted amino-aryl, amino-aryloxy, substituted amino-aryloxy,
wherein within R1-R12, or/and within R13-R16, or/and within R17-R19, or/and between R16 and R19, respectively, two adjacent Rs can form an aromatic ring or a substituted aromatic ring, wherein the substituent is selected from hydrogen, alkyl, substituted alkyl, halide, cyano- or nitro-group, a hydrophilic group, like amino, substituted amino, alkylamino, substituted alkylamino, alkylammonium, substituted alkylammonium, carboxy, carboxylate, carboxylic acid ester, carbamoyl, hydroxy, substituted or unsubstituted alkyloxy, substituted or unsubstituted aryloxy, sulfanyl, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, sulfo, sulfino, sulfeno, sulfonate, sulfinate, sulfenate, sulfamoyl, sulfoxide, phosphono, hydroxyphosphinoyl, hydroxyl-alkyl-phosphinoyl, phosphonate, phosphinate or,
wherein within R1-R12, or/and within R13-R16, or/and within R17-R19, or/and between R16 and R19, respectively, two adjacent Rs can form an aliphatic ring or a substituted aliphatic ring, wherein the substituent is selected from hydrogen, alkyl, substituted alkyl, halide, cyano- or nitro-group, a hydrophilic group, like amino, substituted amino, alkylamino, substituted alkylamino, alkylammonium, substituted alkylammonium, carboxy, carboxylate, carboxylic acid ester, carbamoyl, hydroxy, substituted or unsubstituted alkyloxy, substituted or unsubstituted aryloxy, sulfanyl, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, sulfo, sulfino, sulfeno, sulfonate, sulfinate, sulfenate, sulfamoyl, sulfoxide, phosphono, hydroxyphosphinoyl, hydroxyl-alkyl-phosphinoyl, phosphonate, phosphinate, wherein, if in any of R1-R19 a substitution is present, the substituent in R1-R19 is each independently selected from a halide, cyano- or nitro-group, a hydrophilic group, like an amino, alkylamino, alkylammonium, carboxy, carboxylate, carboxylic acid ester, carbamoyl, hydroxy, alkyloxy, arylalkyloxy, aryloxy, alkylaryloxy, polyethylenoxy, polypropylenoxy, sulfanyl, alkylsulfonyl, arylsulfonyl, sulfo, sulfino, sulfeno, sulfonate, sulfinate, sulfenate, sulfamoyl, sulfoxide, phosphono, hydroxyphosphinoyl, hydroxyl-alkyl-phosphinoyl, phosphonate, phosphinate,
wherein alkyl as used herein is a linear or branched alkyl chain with a length of 1-20 carbon atoms or a heteroalkyl chain with the length of 1-20 atoms comprising 1-4 heteroatoms selected from O, N, P, and S, wherein aryl is a 5, 6, or 7 member aryl ring system, or a 5, 6, or 7 member heteroaryl ring system comprising 1-3 heteroatoms selected from O, S and N,
wherein at least one of R13-R19 is -Q-Z, wherein Q is a linker or a covalent bond, and wherein Z is a functional group.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein Q is a covalent bond or has as a backbone a straight or branched saturated, unsaturated, unsubstituted or substituted C1-C200 alkyl chain, or a 1 to 200 atom chain consisting of carbon atoms, substituted carbon atoms and/or one or more atoms selected from O, N, P and S, or substituted N, P, S atoms, or a chain as described before with the backbone containing one or more cyclic or heterocyclic aromatic or non-aromatic ring systems.

### Claim 3 (depends on 2)

The compound according to claim 2, wherein Q is a covalent bond or has as a backbone a straight or branched saturated, unsaturated, unsubstituted or substituted C1-C100 alkyl chain, or a 1 to 100 atom chain consisting of carbon atoms, substituted carbon atoms and/or one or more atoms selected from O, N, P and S, or substituted N, P, or S atoms, or a chain as described before with the backbone containing one or more cyclic or heterocyclic aromatic or non-aromatic ring systems.

### Claim 4 (depends on 3)

The compound according to claim 3, wherein Q is a covalent bond or has as a backbone a straight or branched saturated, unsaturated, unsubstituted or substituted C1-050 alkyl chain, or a 1 to 50 atom chain consisting of carbon atoms, substituted carbon atoms and/or one or more atoms selected from O, N, P and S, or substituted N, P, or S atoms, or a chain as described before with the backbone containing one or more cyclic or heterocyclic aromatic or non-aromatic ring systems.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein Q is a covalent bond or has as a backbone a straight or branched saturated, unsaturated, unsubstituted or substituted C1-C20 alkyl chain, or a 1 to 20 atom chain consisting of carbon atoms, substituted carbon atoms and/or one or more atoms selected from O, N and S, or a chain as described before with the backbone containing one or more cyclic or heterocyclic aromatic or non-aromatic ring systems.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein the functional group Z is selected from the group consisting of aldehyde, carboxylic acid, carboxylic acid ester, epoxide, N-hydroxysuccinimide ester, amino group, halogen, hydrazine, hydroxyl, sulfhydryl, maleimido, alkynyl, azide, isocyanate, isothiocyanate and phosphoramidite.

### Claim 7 (depends on 1)

The compound of claim 1, further comprising an affinity binding agent covalently bound thereto.

### Claim 8 (depends on 7)

The compound of claim 7, wherein the affinity binding agent is selected from the group consisting of antigen and antibody, biotin or biotin analogue and avidin or streptavidin, sugar and lectin, nucleic acid or nucleic acid analogue and complementary nucleic acid and receptor and ligand.

### Claim 9 (depends on 7)

The compound of claim 7, wherein said affinity binding agent is a nucleic acid or an antibody.

### Claim 10 (depends on 7)

A method for measuring an analyte by an in vitro method, the method comprising the steps of
a) providing a sample suspected or known to comprise the analyte,
b) contacting said sample with a conjugate according to claim 7 under conditions appropriate for formation of an analyte conjugate complex, and
c) measuring the complex formed in step (b) and thereby obtaining a measure of the analyte.

### Claim 11 (depends on 1)

A compound according to Formula II
wherein R1 to R20 are as defined for Formula I in claim 1 with the exception that Q of Formula I is Q1 or Q2 in Formula II, respectively, wherein Q1 is a linker, wherein at least one of R13-R20 in Formula I (b) is Q2 and each Q2 independently is a linker or a covalent bond, wherein (n) is an integer from 1 to 50 and wherein Z is a functional group.

### Claim 12 (depends on 11)

The compound according to claim 11, wherein Formula I (a) and Formula I (b) are the same, except for Q1-Z in Formula I (a) and Q2 in Formula I (b), respectively.