# US 2014/0154716 A1 · Luminogenic and fluorogenic compounds and methods to detect molecules or conditions

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0154716 A1
- Document ID: US20140154716A1
- Status: Published application
- Kind: A1
- Application number: 13/913,919
- Filed: 2013-06-10
- Published: 2014-06-05
- Earliest claimed: 2005-05-31
- Assignees: Promega Corporation
- Applicants: Promega Corporation
- Inventors: James J. Cali; William Daily; Erika Hawkins; Dieter Klaubert; Jianquan Liu; Poncho Meisenheimer; Michael Scurria; John W. Shultz; James Unch; Michael P. Valley; Keith V. Wood; Wenhui Zhou
- Web page: https://patentgrep.com/patent/US20140154716A1

## CPC

- C07D 277/66: with aromatic rings or ring systems directly attached in position 2
- C07D 277/68: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D 311/16: substituted in position 7
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/14: containing three or more hetero rings
- C07D 493/10: Spiro-condensed systems
- C07F 9/65583: {each of the hetero rings containing nitrogen as ring hetero atom}
- C09B 11/24: Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes}
- C09B 19/00: Oxazine dyes
- C09B 57/00: Other synthetic dyes of known constitution
- C09B 57/02: Coumarine dyes
- C12Q 1/66: involving luciferase
- G01N 2500/00: Screening for compounds of potential therapeutic value
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C12Q: MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS (immunoassay G01N33/53); COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- 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

A method to detect the presence or amount of at least one molecule in a sample which employs a derivative of luciferin or a derivative of a fluorophore is provided. Compounds and compositions for carrying out the methods of the invention are also provided.

## Claims

### Claim 1

A compound of formula (X) or a salt thereof:
wherein
R1 is H, C1-6alkyl, phenylC1-6alkyl, or hydroxyC1-6alkyl;
R2 is C1-6alkyl, phenylC1-6alkyl, or hydroxyC1-6alkyl;
wherein any alkyl or phenyl group of R1 and R2 can optionally be substituted with one or two amino groups; and
wherein any amino group substituent of R1 and R2 can be substituted with one or two optionally substituted C1-6alkyl, C1-6alkylcarbonyl, or C1-6alkoxycarbonyl groups.

### Claim 2 (depends on 1)

The compound or salt thereof of claim 1, wherein the —CO2H substituent on the thiazole ring of formula (X) is in the (S) stereochemical configuration.

### Claim 3 (depends on 2)

The compound or salt thereof of claim 2, wherein R1 is H and R2 is unsubstituted phenylC1-6alkyl.

### Claim 4 (depends on 2)

The compound or salt thereof of claim 2, wherein R1 is H and R2 is phenylC1-6alkyl, and phenyl is substituted with amino, optionally substituted C1-6alkylamino, or optionally substituted di-C1-6alkylamino.

### Claim 5 (depends on 2)

The compound or salt thereof of claim 2, wherein R1 is H and R2 is phenylC1-6alkyl, wherein phenyl is substituted with amino, and the amino group is substituted with optionally substituted C1-6alkylcarbonyl or C1-6alkoxycarbonyl.

### Claim 6 (depends on 2)

A luciferase substrate comprising a compound of claim 2.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R1 is H and R2 is methyl, ethyl, propyl, butyl, pentyl, or hexyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R1 is methyl, ethyl, propyl, butyl, pentyl, or hexyl, and R2 is methyl, ethyl, propyl, butyl, pentyl, or hexyl.

### Claim 9 (depends on 1)

The compound of claim 1, wherein R1 is H and R2 is benzyl, phenethyl, phenylpropyl, phenylbutyl, phenylpentyl, or phenylhexyl.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R1 is H and R2 is benzyl, phenethyl, phenylpropyl, phenylbutyl, phenylpentyl, or phenylhexyl wherein the benzene ring of R2 is substituted with an amino group.

### Claim 11 (depends on 1)

The compound of claim 1 having any one of the following structures:

### Claim 12

A compound represented by the following general formula (I) or a salt thereof:
wherein
R1 and R2 independently represent hydrogen, a C1-6alkyl group which may be substituted, or a group represented by formula (A):
wherein X1 and X2 independently represent hydrogen or —N(R3)(R4), wherein R3 and R4 independently represent hydrogen a C1-6 alkyl group which may be substituted, a C1-6 alkylcarbonyl group which may be substituted, or a C1-6 alkoxycarbonyl group which may be substituted; and
n represents an integer of 1 to 6;
provided that R1 and R2 do not simultaneously represent hydrogen.

### Claim 13 (depends on 12)

The compound or a salt thereof according to claim 12, wherein either one of R1 and R2 is hydrogen, and the other is a group represented by the formula (A), and in the formula (A), X1 and X2 both are hydrogen atoms, and n is an integer of 1 to 6.

### Claim 14 (depends on 12)

The compound or a salt thereof according to claim 12, wherein either one of R1 and R2 is hydrogen, and the other is a group represented by the formula (A), and in the formula (A), X1 is hydrogen, and X2 is a group represented as —N(R3)(R4), wherein R3 and R4 independently represent hydrogen, or a C1-6 alkyl group which may be substituted.

### Claim 15 (depends on 12)

The compound or a salt thereof according to claim 12, wherein either one of R1 and R2 is hydrogen, and the other is a group represented by the formula (A), and in the formula (A), X1 is hydrogen, and X2 is a group represented as —N(R3)(R4), wherein either one of R3 and R4 is hydrogen, and the other is a C1-6alkylcarbonyl group which may be substituted, or a C1-6alkyloxycarbonyl group which may be substituted.

### Claim 16 (depends on 12)

A composition comprising a luciferase substrate and an aqueous carrier, wherein the luciferase substrate is a compound of claim 12.