WO2025187876A1 - Compound which changes color by reacting with bodily substance - Google Patents

Abstract

The present specification discloses a compound. The present specification may disclose, as a colored compound or a composition comprising same, a compound having no or negligible color change or a composition comprising same. In addition, the present specification may disclose a compound which visibly turns red when reacting with a bodily substance, or a composition comprising same.

Description

A compound that changes color by reacting with body components

This specification discloses a compound. More specifically, the compound disclosed herein may be a colored compound, meaning that it may exhibit no or negligible color change over time. Furthermore, even more specifically, the compound disclosed herein may be a compound that undergoes a color change upon reaction with a component of the body.

Typically, urine tests are performed as a method of in vitro diagnostics to detect information about the animals' internal organs.

For example, a compound containing a component that can react with various components contained in urine is applied to a substrate, and then urine is sprayed onto the substrate during diagnosis, thereby reacting the applied compound with the urine, thereby detecting biological information.

However, these conventional methods have been problematic, with compounds or compositions containing them applied to the substrate turning brown after a certain period of time. These phenomena raise doubts about the quality or accuracy of the substrate (or detection equipment) and can lower the reliability of detection results for those detecting body information.

Accordingly, it is necessary to provide a compound that exhibits little color change in the compound or substrate at the time of provision and use, and exhibits a distinct color change at the time of use, thereby enabling the acquisition of information in the body.

The present specification discloses a compound.

Additionally, the present specification may disclose a colored compound or a composition containing the same, wherein the color change is negligible or absent.

Additionally, the present specification may disclose a compound or a composition containing the compound that exhibits a distinct red color change when reacting with a component in the body.

In order to solve the above problem, a compound including a tertiary amine group is disclosed, wherein each of the first substituent and the second substituent includes a unit derived from an alkyl group or an acyl group having 1 to 5 carbon atoms and including at the terminal any one of a benzene group, a benzene group substituted with ethoxy or methoxy, and a naphthalene group, and the third substituent includes a compound represented by the following general formula 1.

[General Formula 1]

C _n H _2n NR ₁ R ₂

In general formula 1, R ₁ and R ₂ are each independently a phenyl group, a naphthalene group, a monovalent hydrocarbon group, or hydrogen, and n is a number in the range of 1 to 10.

In addition, the present invention may disclose a compound in which the first substituent and the second substituent equally include a unit derived from an alkyl group or an acyl group having 1 to 5 carbon atoms, which includes at the terminal any one of a benzene group, a benzene group substituted with ethoxy or methoxy, and a naphthalene group.

In addition, the present invention may disclose a compound in which, in the general formula 1, either one of R ₁ and R ₂ essentially contains a naphthalene group.

In addition, the present invention may disclose a compound comprising a chemical formula derived from the following general formula 2.

[General Formula 2]

H ₂ NR ₃ SO ₂ NR ₄ R ₅

In general formula 3, R ₃ is an alkyl group having 1 to 10 carbon atoms, an alkylene group having 2 to 10 carbon atoms, or a benzene group, and R ₄ and R ₅ are each independently a monovalent hydrocarbon group, an alkyl group having 1 to 5 carbon atoms, or hydrogen.

In addition, the present invention may disclose a compound further comprising the following chemical formula 1, wherein the chemical formula 1 is a compound formed under acidic conditions, wherein the chemical formula derived from the general formula 2 is a compound.

[Chemical Formula 1]

In chemical formula 1, R ₆ and R ₇ are each independently a monovalent hydrocarbon group, an alkyl group having 1 to 5 carbon atoms, or hydrogen.

In addition, the present invention may disclose a compound wherein the acidic condition includes at least one of nitrous acid (HNO ₂ ), fluoroboric acid (HBF ₄ ), sulfuric acid (H ₂ SO ₄ ), and hydrochloric acid (HCl).

The present invention may also disclose a compound further comprising a compound corresponding to a diazonium salt.

The present invention may also disclose a composition comprising the compound described above.

The present specification discloses a compound. The present specification may disclose a colored compound or a composition comprising the same, wherein the color change is negligible or absent. The present specification may also disclose a compound or a composition comprising the same, which exhibits a distinct red color change upon reaction with a component of the body.

Meanwhile, the effects that can be obtained from the present invention are not limited to the effects mentioned above, and other effects that are not mentioned can be clearly understood by a person having ordinary skill in the technical field to which the present invention belongs from the description below.

Figures 1a and 1b are NMR of compound B.

Figures 2a and 2b are NMR of compound C.

Figures 3a and 3b are NMR of compound D.

Figure 4 shows the results of observing the color and color change of an embodiment according to the present invention.

Hereinafter, the compounds according to the present invention will be described in detail. However, the scope of the compounds is not limited by the following description.

Among the properties mentioned in this specification, properties whose results are affected by the measurement temperature are the results measured at room temperature, unless otherwise specifically stated.

Among the properties mentioned in this specification, properties whose results are affected by the measurement temperature are the results measured at room temperature, unless otherwise specifically stated.

The term room temperature means a natural temperature that has not been artificially heated or cooled, for example, a temperature within the range of 10°C to 30°C, or about 23°C or about 25°C.

Unless otherwise specified in this specification, the unit of temperature is ℃.

Among the properties mentioned in this specification, if pressure affects the results, unless otherwise specified, the properties are measured at atmospheric pressure. The term atmospheric pressure refers to natural pressure that has not been artificially pressurized or depressurized, and is typically within the range of approximately 700 mmHg to 800 mmHg.

Among the properties mentioned in this specification, if humidity affects the results, unless otherwise specified, the properties are measured at standard humidity. Standard humidity means any humidity within the range of 40% to 60% relative humidity, for example, a relative humidity of approximately 40% or 60%.

The present invention relates to a compound.

The present specification discloses a compound comprising a tertiary amine group. A tertiary amine group means an amine having three substituents, or an ammonia (NH3) in which all three hydrogens are replaced by substituents other than hydrogen.

In this specification, for the convenience of description, each substituent of the tertiary amine group is described as a first substituent, a second substituent, and a third substituent. However, these first to third substituents are for the convenience of description, and so their positions or orders are not particularly limited as long as they satisfy the first to third substituents disclosed in this specification.

For example, the compound comprising the tertiary amine group may include a unit derived from an alkyl group or an acyl group having 1 to 5 carbon atoms, each of which includes, as the first substituent and the second substituent, one of a benzene group, a benzene group substituted with ethoxy or methoxy, and a naphthalene group at the terminal.

For example, if the first substituent or the second substituent is a unit derived from an alkyl group or acyl group having 1 to 5 carbon atoms and including a benzene group at the terminal, it may mean a structure in which the terminal of an alkyl group or acyl group having 1 to 5 carbon atoms and directly connected to nitrogen (N) is substituted with a benzene group.

Also, for example, when the first substituent or the second substituent is a unit derived from an alkyl group or acyl group having 1 to 5 carbon atoms and including a benzene group substituted with ethoxy or methoxy at the terminal, it means a structure in which the terminal of the alkyl group or acyl group having 1 to 5 carbon atoms and directly connected to nitrogen (N) is substituted with a benzene group, and the benzene group substituted at the terminal of the alkyl group or acyl group having 1 to 5 carbon atoms and directly connected to nitrogen (N) can mean that the para-position is substituted with ethoxy or methoxy.

The compound disclosed herein may be a compound in which the first substituent and the second substituent identically include a unit derived from an alkyl group or an acyl group having 1 to 5 carbon atoms, which includes at the terminal any one of a benzene group, a benzene group substituted with ethoxy or methoxy, and a naphthalene group.

The meaning that the first substituent and the second substituent include the same unit derived from an alkyl group or acyl group having 1 to 5 carbon atoms is that the structural formula on the plane is the same regardless of the chemical stereostructure, for example, regardless of the RS system or the chiral structure.

In addition, for example, when the first substituent and the second substituent include the same unit derived from an acyl group having at least one of a benzene group, a benzene group substituted with ethoxy or methoxy, and a naphthalene group at the end, one of the benzene group, the benzene group substituted with ethoxy or methoxy, and the naphthalene group contained in the acyl group may be included as one at the end of the acyl group of the first substituent and the end of the acyl group of the second substituent, so that the first substituent and the second substituent may form a structure in which the benzene group, the benzene group substituted with ethoxy or methoxy, and the naphthalene group are connected. For example, when the first substituent and the second substituent are units derived from an acyl group having at least one benzene group at the end, the tertiary amine may correspond to a phthalimide group.

Additionally, the third substituent may be a compound represented by the following general formula 1.

[General Formula 1]

CnH2nNR1R2

In general formula 1, R1 and R2 can each independently be a phenyl group, a naphthalene group, a monovalent hydrocarbon group, or hydrogen.

For example, if at least one of R1 and R2 is a phenyl group or a naphthalene group, the compound may be a dye compound and thus advantageous in color change. More specifically, in the compounds disclosed herein, at least one of R1 and R2 may essentially include a naphthalene group. This naphthalene group has a structure in which two benzene groups are fused, and may be advantageous in immediately exhibiting a color change when reacted with a compound that reacts with the compounds disclosed herein.

Also, in general formula 1, n is a number within the range of 1 to 10. Preferably, n may be a number within the range of 1 to 6, and more preferably, 2 to 5.

The compound disclosed in this specification may be a compound having a chemical formula derived from the following general formula 2.

[General Formula 2]

H2NR3SO2NR4R5

In general formula 2, R3 can be an alkyl group, an alkylene group, or a benzene group.

When the above R3 is an alkyl group, the lower limit of the carbon number of the alkyl group may be about 1, 2, 3, 4, 5 or 6, and the upper limit may be about 10, 9, 8, 7, 6 or 5. The carbon number of the alkyl group may be within a range exceeding or equal to the aforementioned lower limit or less than or equal to the aforementioned upper limit.

In addition, when the above R3 is an alkylene group, the lower limit of the carbon number of the alkylene group may be about 2, 3, 4, 5, or 6, and the upper limit may be about 10, 9, 8, 7, 6, 5, or 4. The carbon number of the alkylene group may be in a range exceeding or equal to the aforementioned lower limit or less than or equal to the aforementioned upper limit. The alkylene group is in a form in which one hydrogen is removed from the carbons at both ends, and is different from an arylene group in which two hydrogens are removed from one carbon.

In the general formula 2 above, the meaning that R3 is an alkyl group, an alkylene group, or a benzene group may mean that in the chemical formula derived from the general formula 2, N and SO2 are connected (or bonded) as an alkyl group, an alkylene group, or a benzene group.

Also, in general formula 2, R4 and R5 can each independently be a monovalent hydrocarbon group, an alkyl group, or hydrogen.

When at least one of the above R4 and R5 is an alkyl group, the lower limit of the carbon number of the alkyl group may be 1, and the upper limit may be about 5, 4, 3, or 2. The carbon number of the alkyl group may be in a range exceeding or equal to the aforementioned lower limit or less than or equal to the aforementioned upper limit.

The compound disclosed in this specification may be a compound further comprising the following chemical formula 1, wherein the chemical formula 1 is a compound formed under acidic conditions with a chemical formula derived from the general formula 2.

[Chemical Formula 1]

In chemical formula 1, R6 and R7 are each independently a monovalent hydrocarbon group, an alkyl group having 1 to 5 carbon atoms, or hydrogen. Since chemical formula 4 corresponds to a chemical formula derived from the aforementioned general formula 2, the description of R6 and R7 is the same as R4 and R5 of the aforementioned general formula 2.

The compound disclosed herein may be a compound in which the acidic condition under which the chemical formula 1 is formed includes at least one of nitrous acid (HNO2), fluoroboric acid (HBF4), sulfuric acid (H2SO4), and hydrochloric acid (HCl).

The compound disclosed herein may be a compound further comprising a compound corresponding to a diazonium salt.

In addition, the diazonium salt may be a salt formed by losing electrons under acidic conditions, having a chemical formula derived from the general formula 2 described above.

The compounds disclosed herein or compositions containing the compounds may exhibit a certain level of color or more. As used herein, color refers to the degree to which the compound or composition containing the compound itself exhibits color when observed with the naked eye.

A color can be produced by reacting a compound containing the tertiary amine group described above with a compound containing a chemical formula derived from the general formula 2 described above.

For example, it is difficult to visually detect a color change in a colored compound or a composition containing the same during the storage process compared to a colorless compound or a composition containing the same.

Accordingly, the colored compound or the composition containing it or the substrate on which the compound or the composition containing it is applied may have the advantage of showing little change in color over time as seen with the naked eye, thereby preventing quality deterioration or a decrease in the reliability of the results.

Additionally, the compounds disclosed herein or compositions containing them may exhibit a red color upon reaction with a component within the body. As used herein, the color red encompasses all colors in the red family, including pink, scarlet, purple, and red. Furthermore, the component within the body may be, for example, sodium nitrite (NaNO2).

When the compound or composition containing the compound reacts with a component in the body, a red color appears, and the red color may become darker over time.

The compounds or compositions containing the compounds disclosed herein may be used to detect biometric information. Methods for detecting biometric information using saliva, such as urine, are known.

The method by which the compound disclosed herein or the composition containing the compound may react with sodium nitrite, such as adding sodium nitrite to the compound disclosed herein or the composition containing the compound, or adding the compound disclosed herein or the composition containing the compound to sodium nitrite, is not particularly limited. In addition, in addition to addition, a method may be used in which the compound or the composition containing the compound is applied to a substrate and then reacted with sodium nitrite, and such a reaction method is also not particularly limited. In addition, the substrate may be exemplified by glass, a resin film, and natural cotton, but is not particularly limited as long as it is a method that can be considered by a person skilled in the art.

Hereinafter, the present invention will be described in more detail through specific experimental examples. However, these experimental examples are intended to exemplify the present invention and the scope of the present invention is not limited to these experimental examples.

Manufacturing Example 1 - Compound A

Compound A having a chemical formula derived from general formula 2 was prepared. Compound A is the following compound in which R5 is a benzene group and R6 and R7 are hydrogen in general formula 2.

[Compound A]

Manufacturing Example 2 - Compound B

Compound B containing a tertiary amine group was prepared by adding 103.6 mg of 1-naphthylethylenediamine dihydrochloride, 44.8 mg of KOH, and 108.9 μL of 4-Methoxybenzyl chloride to 4 mL of DMSO solvent at 0 °C and synthesizing for 5 hours. The molar mass of compound B is 426.56 g/mol. The NMR of compound B is as shown in Figures 1a and 1b.

Here, Fig. 1a and Fig. 1b are representations of a single drawing separated by line A, with Fig. 1a representing the left side and Fig. 1b representing the right side.

[Compound B]

Manufacturing Example 3 - Compound C

At 0°C, 103.6 mg of 1-naphthylethylenediamine dihydrochloride and 57.0 μL of benzyl bromide were added to 4 mL of THF solvent, stirred for 10 hours, and then 165.8 mg of K2CO3 was added. Compound C containing a tertiary amine group was synthesized at room temperature (approximately 25°C) for 12 hours. The molar mass of compound C is 366.51 g/mol. The NMR of compound C is as shown in Figures 2a and 2b.

Here, FIG. 2a and FIG. 2b are representations of a single drawing separated by line B, with FIG. 2a representing the left side and FIG. 2b representing the right side.

[Compound C]

Manufacturing Example 4 - Compound D

At room temperature (approximately 25°C), 103.6 mg of 1-naphthylethylenediamine dihydrochloride and 80 μL of Et3N were added to 4 mL of MeOH solvent, stirred for 20 minutes, 71.1 mg of phthalic anhydride was added, and then synthesized in a reflux apparatus at approximately 115°C for 6 hours to prepare compound D containing a tertiary amine group. The molar mass of compound D is 316.36 g/mol. The NMR of compound D is as shown in Figures 3a and 3b.

Here, Figures 3a and 3b represent a single drawing divided by line C, with Figure 3a representing the left side and Figure 3b representing the right side.

[Compound D]

Color before reaction

Example 1

5 mg of compound A prepared in Manufacturing Example 1 was mixed with 1 mL of 5% sulfuric acid to prepare 4 mL of composition A, and compound B prepared in Manufacturing Example 2 was mixed with the composition A at a ratio of 1:1.

Example 2

The mixture was mixed in the same manner as in Example 1, except that Compound C prepared in Manufacturing Example 3 was included instead of Compound B.

Example 3

The mixture was mixed in the same manner as in Example 1, except that Compound D prepared in Manufacturing Example 4 was included instead of Compound B.

Color change after NaNO ₂ reaction

A composition containing 0.1 mg of NaNO ₂ diluted with 1 mL of H ₂ O was dropped into the mixture of Examples 1 to 3, which confirmed the colorability before the above reaction, and the color change was observed immediately thereafter. In addition, the color change was observed 10 minutes after the addition of NaNO ₂ .

NO ⁺ formed by NaNO ₂ reacts with -NH ₂ of compound A prepared in Manufacturing Example 1 to form a diazonium salt, and the diazonium salt thus formed reacts with any one of compounds B to D prepared in Manufacturing Examples 2 to 4 to form an Azo dye containing a naphthalene group and a benzene group with an N≡N bond therebetween, thereby expressing a red color.

Figure 4 shows the results of observing the color and color change of the example.

The mixtures of Examples 1 to 3 are colored even before reacting with NaNO _2. In addition, when NaNO ₂ is added and the reaction proceeds, an Azo dye is quickly formed, causing a color change, and when the reaction has elapsed for about 10 minutes, an even darker color is exhibited. Through this, it was confirmed that the compound disclosed in the present specification or a composition containing the same may be a compound or a composition containing the same that is colored before reacting with a biological component and does not or cannot detect a color change.

In addition, it was confirmed that the compound disclosed in the present specification or a composition containing the same can be a compound or a composition containing the same that can identify a biological component by exhibiting a color change after reaction with the biological component.

The above description of the present invention is for illustrative purposes only, and those skilled in the art will readily appreciate that the present invention can be readily modified into other specific forms without altering the technical spirit or essential characteristics of the present invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

The scope of the present invention is indicated by the claims described below rather than the detailed description above, and all changes or modifications derived from the meaning and scope of the claims and their equivalent concepts should be interpreted as being included in the scope of the present invention.

Claims (8)

As a compound containing a tertiary amine group, Each of the first substituent and the second substituent comprises a unit derived from an alkyl group or an acyl group having 1 to 5 carbon atoms, which includes at the terminal any one of a benzene group, a benzene group substituted with ethoxy or methoxy, and a naphthalene group, The third substituent is a compound including a compound represented by the following general formula 1: [General Formula 1] C _n H _2n NR ₁ R ₂ In general formula 1, R ₁ and R ₂ are each independently a phenyl group, a naphthalene group, a monovalent hydrocarbon group, or hydrogen, and n is a number in the range of 1 to 10. In the first paragraph, A compound in which the first substituent and the second substituent identically contain a unit derived from an alkyl group or an acyl group having 1 to 5 carbon atoms, which includes at the terminal any one of a benzene group, a benzene group substituted with ethoxy or methoxy, and a naphthalene group. In the first paragraph, A compound in which, in the above general formula 1, either R ₁ or R ₂ essentially contains a naphthalene group. In the first paragraph, A compound comprising a chemical formula derived from the following general formula 2: [General Formula 2] H ₂ NR ₃ SO ₂ NR ₄ R ₅ In general formula 3, R ₃ is an alkyl group having 1 to 10 carbon atoms, an alkylene group having 2 to 10 carbon atoms, or a benzene group, and R ₄ and R ₅ are each independently a monovalent hydrocarbon group, an alkyl group having 1 to 5 carbon atoms, or hydrogen. In paragraph 4, A compound further comprising the following chemical formula 1, The above chemical formula 1 is a compound in which the chemical formula derived from the above general formula 2 is formed under acidic conditions: [Chemical Formula 1] In chemical formula 1, R ₆ and R ₇ are each independently a monovalent hydrocarbon group, an alkyl group having 1 to 5 carbon atoms, or hydrogen. In paragraph 5, A compound wherein the acidic condition includes at least one of nitrous acid (HNO ₂ ), fluoroboric acid (HBF ₄ ), sulfuric acid (H ₂ SO ₄ ), and hydrochloric acid (HCl). In the first paragraph, A compound further comprising a compound corresponding to a diazonium salt. A composition comprising a compound of any one of claims 1 to 7.