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KR-20260067981-A - NOVEL COMPOUNDS

KR20260067981AKR 20260067981 AKR20260067981 AKR 20260067981AKR-20260067981-A

Abstract

The present invention relates to a compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, R is a substitutable linear or branched C1 - C20 alkyl group, a substitutable C3 - C20 cycloalkyl group, or a substitutable C6 - C20 aryl group, and The above substitution is by oxygen, nitrogen, sulfur, hydroxyl, linear or branched C1 - C6 alkyl groups, C3 - C20 cycloalkyl groups, C6 - C20 aryl groups, halogens, or combinations thereof).

Inventors

  • 김경민
  • 김은하
  • 하지선
  • 송찬호
  • 사자드 무하마드 아자르

Assignees

  • 아주대학교산학협력단
  • 대한민국(질병관리청 국립보건연구원장)

Dates

Publication Date
20260513
Application Date
20251014
Priority Date
20241106

Claims (9)

  1. Compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, R is a substitutable linear or branched C1 - C20 alkyl group, a substitutable C3 - C20 cycloalkyl group, or a substitutable C6 - C20 aryl group, and The above substitution is by oxygen, nitrogen, sulfur, hydroxyl, linear or branched C1 - C6 alkyl groups, C3 - C20 cycloalkyl groups, C6 - C20 aryl groups, halogens, or combinations thereof).
  2. In Article 1, A compound represented by the above chemical formula 1, comprising any one of the following compounds: ; ; ; ; ; ; ; ; ; ; ; .
  3. A step of preparing a compound represented by the following chemical formula 4 by reacting a compound represented by the following chemical formula 2 and a compound represented by the following chemical formula 3; A step of preparing a compound represented by the following chemical formula 6 by reacting a compound represented by the above chemical formula 4 with a compound represented by the following chemical formula 5; and A step of preparing a compound represented by Chemical Formula 1 of Claim 1 by substituting a hydroxyl group of a compound represented by Chemical Formula 6 above; including, Method for preparing a compound according to claim 1: [Chemical Formula 2] (In the above Chemical Formula 2, X1 is a halogen or B(OH) 2 ) [Chemical Formula 3] (In the above Chemical Formula 3, X₂ is a halogen or B(OH) ₂ ) [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] .
  4. In Paragraph 3, Of the above X1 and X2 , one is a halogen and the other is B(OH) 2 , Method for manufacturing a compound according to claim 1.
  5. A pharmaceutical composition for preventing or treating HBV infection, comprising a compound according to claim 1 as an active ingredient.
  6. In Article 5, The above pharmaceutical composition comprises a pharmaceutically acceptable carrier.
  7. In Article 6, A pharmaceutical composition comprising the carrier selected from the group consisting of lactose, dextrose, sucrose, sorbitol, mannitol, starch, acacia gum, calcium phosphate, alginate, gelatin, calcium silicate, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup, methyl cellulose, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, menthol, mineral oil, and combinations thereof.
  8. In Article 5, The above pharmaceutical composition further comprises a component selected from the group consisting of preservatives, solubilizers, stabilizers, humectants, sweeteners, coloring agents, flavoring agents, salts, buffers, antioxidants, lubricants, emulsifiers, suspending agents, preservatives, and combinations thereof.
  9. In Article 5, The above pharmaceutical composition is administered by a method selected from the group consisting of intraperitoneal administration, oral administration, inhalation administration, intravenous administration, intramuscular administration, subcutaneous administration, dermal administration, intrauterine administration, tumor administration, rectal administration, and combinations thereof.

Description

Novel Compounds The present invention relates to a novel compound. Hepatitis B virus (HBV) is one of the major pathogens causing serious health problems worldwide. According to the World Health Organization (WHO), approximately 250 million people are infected with chronic hepatitis B, and about 900,000 people die each year from hepatitis B-related complications. Currently, nucleoside/nucleotide analogs and interferon-alpha are primarily used to treat hepatitis B. However, these treatments have drawbacks, such as difficulty in achieving complete viral elimination, the development of resistance with long-term administration, and side effects. Therefore, there is an urgent need for the development of anti-HBV drugs with novel mechanisms of action. Recent studies have revealed that the sirtuin protein family plays a crucial role in the HBV life cycle. In particular, Sirtuin 2 (SIRT2) is known to act as an important regulator in the process of HBV replication. Consequently, interest in developing inhibitors targeting SIRT2 is growing. AGK2 is one of the well-known SIRT2 inhibitors that demonstrated an inhibitory effect on HBV proliferation in in vitro experiments; however, its clinical application has been limited due to low selectivity and side effects. Therefore, there is a need to develop new variants based on the structure of AGK2. Korean Public Patent No. 10-2020-0123392, which is the background technology of the present invention, relates to a composition for inhibiting the proliferation of hepatitis B virus and a method thereof. Figure 1 is the NMR spectrum of a compound according to Example 1 of the present invention. Figure 2 is the NMR spectrum of a compound according to Example 2 of the present invention. Figure 3 is the NMR spectrum of a compound according to Example 3 of the present invention. Figure 4 is the NMR spectrum of a compound according to Example 4 of the present invention. Figure 5 is the NMR spectrum of a compound according to Example 5 of the present invention. Figure 6 is the NMR spectrum of a compound according to Example 6 of the present invention. Figure 7 is the NMR spectrum of a compound according to Example 7 of the present invention. Figure 8 is the NMR spectrum of a compound according to Example 8 of the present invention. Figure 9 is the NMR spectrum of a compound according to Example 9 of the present invention. Figure 10 is the NMR spectrum of a compound according to Example 10 of the present invention. Figure 11 is the NMR spectrum of a compound according to Example 11 of the present invention. Figure 12 is the NMR spectrum of a compound according to Example 12 of the present invention. Figure 13 is the result of a cytotoxicity test according to an experimental example of the present invention. Figure 14 is the result of an HBV proliferation inhibition experiment according to an experimental example of the present invention. Figure 15 is the ELISA result of a compound according to Example 1 (ACTC-004) of the present invention. Figure 16 is the ELISA result of a compound according to Example 3 (ACTC-024) of the present invention. Figure 17 is the ELISA result of a compound according to Example 4 (ACTC-025) of the present invention. Figure 18 is the ELISA result of a compound according to Example 9 (ACTC-047) of the present invention. Figure 19 is the ELISA result of a compound according to Example 11 (ACTC-054) of the present invention. Embodiments of the present invention are described below with reference to the attached drawings to enable those skilled in the art to easily implement the invention. However, the present invention may be embodied in various different forms and is not limited to the embodiments described herein. Furthermore, in order to clearly explain the present invention in the drawings, parts unrelated to the explanation have been omitted, and similar parts throughout the specification are denoted by similar reference numerals. Throughout this specification, when a part is described as being "connected" to another part, this includes not only cases where they are "directly connected," but also cases where they are "electrically connected" with other elements interposed between them. Throughout the entire specification, when a component is described as being located "on," "on top," "on top," "under," "on bottom," or "on bottom" of another component, this includes not only cases where the component is in contact with the other component but also cases where another component exists between the two components. Throughout this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components. As used herein, terms of degree such as “about,” “substantially,” etc., are used to mean at or near the stated value when inherent manufacturing and material tolerances are presented in the stated meaning, and are used to prevent uns