KR102530415B1 - Composition for preventing and treating gastrointestinal diseases, effective for killing Helicobacter pylori - Google Patents
Composition for preventing and treating gastrointestinal diseases, effective for killing Helicobacter pylori Download PDFInfo
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- KR102530415B1 KR102530415B1 KR1020200144574A KR20200144574A KR102530415B1 KR 102530415 B1 KR102530415 B1 KR 102530415B1 KR 1020200144574 A KR1020200144574 A KR 1020200144574A KR 20200144574 A KR20200144574 A KR 20200144574A KR 102530415 B1 KR102530415 B1 KR 102530415B1
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- acid
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- helicobacter pylori
- preventing
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Abstract
본 발명은 하기 화학식 1로 표시되는 화합물을 포함하는 위장 관련 질환 예방 또는 치료를 위한 조성물에 관한 것으로서, 보다 상세하게는 하기 화학식 1로 표시되는 화합물은 그람음성균인 H.pylori에 대해 적은 용량으로 현저한 항균 활성을 가지고, 생체이용률이 높고, 독성이 낮으며, 대량 생산이 용이하여 위암 발생률을 낮추고 위염 억제에 효과적인 의약, 건강보조식품, 식품군에 기능성 원료로 유용하게 사용될 수 있다.
[화학식 1]
[Formula 1]
Description
본 발명은 헬리코박터 파일로리 균 사멸에 효과적인 위장 질환 예방 및 치료용 조성물에 관한 것으로서, 보다 상세하게는 [화학식 1]로 표시되는 화합물, 이의 이성질체, 또는 이의 약학적으로 허용가능한 염을 포함하는 위장 질환 예방 및 치료용 조성물에 관한 것이다.The present invention relates to a composition for preventing and treating gastrointestinal diseases effective in killing Helicobacter pylori bacteria, and more particularly, to a composition for preventing gastrointestinal diseases comprising a compound represented by [Formula 1], an isomer thereof, or a pharmaceutically acceptable salt thereof and therapeutic compositions.
위장 질환의 원인은 다양하며, 헬리코박터 파이로리 균을 비롯한 위산, 펩신, 과로, 스트레스, 알콜 등의 공격인자와 점액, 조직 재생능력, 혈행 개선능력 등 방어인자의 불균형으로 기인한다고 알려져 있다. 과로나 스트레스, 헬리코박터 파이로리 감염 등으로 인한 위염의 발생은 누구나 흔히 경험하는 질병으로서 이를 방치하게 되면 만성위염, 위궤양 등으로 진행되고 결국 위암으로 발전 될 가능성이 있다. 알콜에 의한 위점막의 손상은 자극요인을 배제시킴으로써 수일 내에 정상으로 회복되기도 하나, 심한 경우는 위장관 출혈, 위천공 등이 발생할 수도 있다(오태영 등, 응용약물학회지, 제5권, pp202-210, 1997). 지금까지 시메티딘, 라니티딘, 파모티딘, 오메프라졸이나 비스무스제제 등 다양한 위장질환 치료제들이 개발되어 사용되고 있으나, 이들은 투약 중지시 재발률이 높다는 단점이 있어 새로운 약물의 개발이 필요하다.The causes of gastrointestinal diseases are diverse, and it is known that they are caused by an imbalance of attack factors such as Helicobacter pylori, gastric acid, pepsin, overwork, stress, and alcohol, and defense factors such as mucus, tissue regeneration ability, and blood circulation improvement ability. Occurrence of gastritis due to overwork, stress, Helicobacter pylori infection, etc. is a disease that everyone commonly experiences, and if left unattended, it progresses to chronic gastritis, gastric ulcer, etc., and eventually develops into gastric cancer. Damage to the gastric mucosa caused by alcohol can be restored to normal within a few days by excluding irritating factors, but in severe cases, gastrointestinal bleeding and gastric perforation may occur (Oh Tae-young et al., Journal of Applied Pharmacology, Vol. 5, pp202-210, 1997). Until now, various gastrointestinal disease treatments such as cimetidine, ranitidine, famotidine, omeprazole, or bismuth preparations have been developed and used, but they have a disadvantage in that they have a high recurrence rate when medication is discontinued, requiring the development of new drugs.
헬리코박터 파이로리(Helicobacter pylori)균은 1982년 호주의 Marshall과 [0006] Warren에 의하여 인체의 위점막에서 처음 분리된 이래, 만성위염 및 소화성 궤양의 주요 원인균임이 밝혀졌으며, 1994년에는 세계보건기구 산하 국제 암연구기관에서 발암인자의 하나로 규명되었다. 이 균은 몇 개의 편모를 가진 그람음성 간균으로 위점막층의 표층이나 점액 내에 증식하며 가장 특징적인 미생물학적 성상으로서 강력한 운동성과 유레아제(urease)효소 활성을 가지고 있다.Since Helicobacter pylori was first isolated from the gastric mucosa of the human body by Marshall and Warren in Australia in 1982, it has been found to be a major cause of chronic gastritis and peptic ulcer disease, and in 1994, an international It has been identified as one of the carcinogens by cancer research institutes. This bacterium is a gram-negative bacillus with several flagella, proliferates in the surface layer of the gastric mucosa layer or in the mucus, and has strong motility and urease enzyme activity as the most characteristic microbiological characteristics.
헬리코박터 파이로리균은 강력한 요소 분해효소인 우레아제(urease)를 분비하여 위액내의 요소(H2NCONH2, urea) 1분자를 가수분해하여 2분자의 암모니아(NH3)를 형성한다. 이 세균의 우레아제는 인체 위장관 표피세포에 헬리코박터 파이로리균을 감염시키고, 콜로니화(집락화, colonization)를 돕는 것에 대한 밀접한 관련성이 있다고 보고된다. 구체적으로, 우레아제를 불활성화시킨 헬리코박터 파이로리 균주는 위 점막세포에서 콜로니화하지 못하며, 우레아제 활성이 헬리코박터 파이로리의 콜로니화에 필수적이라는 보고가 있으며(Eaton K.A., et al., Infect Immun., 59, pp2470-2475, 1991), 헬리코박터 파이로리 우레아제에 의해 생성된 암모니아는 위액내 pH를 증가시키고, 위 점액층을 손상시키며(Sidebotham R.L., et al., J. Clin. Pathol., 44, pp52-57, 1991), 암모니아 자체가 위 점액층 세포의 산소소비와 미토콘드리아의 ATP 생성을저해하고(Tsujii M., et al., Gastroenterology, 102, pp1881-1888, 1992), 궁극적으로 암모니아는 모노클로로아민 (monochloroamine)을 형성하여 반응성 산소종(reactive oxygen species)을 생성하기 때문에 세포손상을 유발하여 만성염증을 일으키고, 나아가 DNA 손상을 일으켜 암발생 과정을 촉진시킨다는 보고가 있다(Hahm K.B., et al., Am. J.Gastroenterol., 92, pp1853-1857, 1997).Helicobacter pylori secretes urease, a strong urease, to hydrolyze one molecule of urea (H2NCONH2, urea) in gastric juice to form two molecules of ammonia (NH3). It is reported that urease of this bacterium is closely related to infecting human gastrointestinal epidermal cells with Helicobacter pylori and helping colonization. Specifically, Helicobacter pylori strains inactivated urease fail to colonize in gastric mucosal cells, and it has been reported that urease activity is essential for colonization of Helicobacter pylori (Eaton K.A., et al., Infect Immun., 59, pp2470 -2475, 1991), and ammonia produced by Helicobacter pylori urease increases the pH of gastric juice and damages the gastric mucus layer (Sidebotham R.L., et al., J. Clin. Pathol., 44, pp52-57, 1991). , Ammonia itself inhibits the oxygen consumption of gastric mucus layer cells and mitochondrial ATP production (Tsujii M., et al., Gastroenterology, 102, pp1881-1888, 1992), and ultimately ammonia forms monochloroamine. It has been reported that reactive oxygen species are generated, causing cell damage, causing chronic inflammation, and furthermore, causing DNA damage to accelerate the process of cancer development (Hahm K.B., et al., Am. J. Gastroenterol ., 92, pp1853-1857, 1997).
상기와 같은 헬리코박터 파이로리 균을 억제하기 위해 다양한 항생제 요법이 사용되고 있으나, 항생제 내성 균주의 출현으로 인해 효율성이 떨어지는 문제가 있으며, 이에 헬리코박터 파이로리균에 대한 항균 효과를 가지는 새로운 물질의 발굴이 필요한 실정이다.Although various antibiotic therapies are used to suppress Helicobacter pylori as described above, there is a problem in that efficiency is reduced due to the emergence of antibiotic-resistant strains, and thus, there is a need to discover new substances having an antibacterial effect against Helicobacter pylori.
한편, 양이온성 항균 펩타이드는 보통 20개 내외의 아미노산으로 구성되고, 양전하를 띠는 아미노산들에 의한 양이온성은 박테리아의 외막 또는 세포질막과의 상호작용에 있어서 중요한 역할을 한다. 소수성 그룹의 도입에 의한 소수성은 펩타이드의 소수성 헬릭스 코어 부분이 막지질 아실기 사슬(membrane lipid acylchain)들과 소수성 상호작용(hydrophobic interaction)하여 안정하게 달라붙을 수 있도록 한다. 소수성 그룹이 제거된 변형체의 경우 그람 음성균에 대한 활성이 저하되는 것으로 보고된 바 있다. 반면, 양이온성 항균 펩타이드는 그 구조가 복잡하여 합성 및 구조 활성 상관관계 연구에 고비용이 따르며, 용혈작용(적혈구의 파괴)과 같은 심각한 단점을 가지고 있다.On the other hand, cationic antibacterial peptides are usually composed of about 20 amino acids, and cationicity by positively charged amino acids plays an important role in interaction with the bacterial outer membrane or cytoplasmic membrane. Hydrophobicity by the introduction of a hydrophobic group enables the hydrophobic helix core portion of the peptide to stably attach to membrane lipid acyl chains through hydrophobic interaction. It has been reported that activity against Gram-negative bacteria is reduced in the case of variants in which the hydrophobic group is removed. On the other hand, cationic antibacterial peptides have a complicated structure, so they are expensive for synthesis and structure-activity correlation studies, and have serious disadvantages such as hemolysis (destruction of red blood cells).
본 발명자들은 항균 펩타이드의 문제점을 해결하기 위한 대안으로, 양이온성 그룹과 소수성 그룹을 포함하는 양친매성 저분자 화합물에 대한 연구를 거듭하여, 그 결과, 트리아진 모핵에 아민 또는 구아니딘을 포함하는 양이온성 그룹과 소수성 잔기를 도입하여, 조절된 용혈작용은 물론 높은 항균 활성을 갖는 펩티도미메틱 물질을 고안한 바 있다(대한민국 등록특허 제10-2022323호).As an alternative to solving the problems of antimicrobial peptides, the present inventors have repeatedly studied amphiphilic low-molecular compounds containing cationic and hydrophobic groups, and as a result, cationic groups containing amines or guanidines in the triazine moiety A peptidomimetic substance having controlled hemolysis as well as high antibacterial activity has been designed by introducing hydrophobic residues (Korean Patent Registration No. 10-2022323).
이에, 본 발명자들은 이런 항균 펩티도미메틱 중 특정 물질이 그람 양성균에서도 효과적인 세균 사멸을 보일 뿐만 아니라, 그람 음성균인 H. pylori에서 훨씬 더 뛰어난 항균 효과를 보이는 것을 확인함으로써, 본 발명을 완성하였다. Accordingly, the inventors of the present invention completed the present invention by confirming that a specific substance among these antibacterial peptidomimetics not only shows effective bacterial killing even in Gram-positive bacteria, but also shows a much superior antibacterial effect in Gram-negative bacteria, H. pylori .
본 발명의 목적은 하기 화학식 1로 표시되는 화합물을 이용한 위장 질환의 예방, 개선 또는 치료용 조성물을 제공하는 것이다.An object of the present invention is to provide a composition for preventing, improving or treating gastrointestinal diseases using a compound represented by Formula 1 below.
본 발명의 또다른 목적은 상기 화학식 1로 표시되는 화합물을 이용한 헬리코박터 파이로리 균의 감염 또는 증식 억제용 조성물을 제공하는 것이다.Another object of the present invention is to provide a composition for inhibiting the infection or growth of Helicobacter pylori bacteria using the compound represented by Formula 1.
상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 위장 질환의 예방 및 치료용 약학적 조성물을 제공한다:In order to achieve the above object, the present invention provides a pharmaceutical composition for preventing and treating gastrointestinal diseases containing a compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient:
[화학식 1][Formula 1]
또한, 본 발명은 상기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 염을 유효성분으로 함유하는 위장 질환의 예방 및 개선용 건강기능식품 조성물을 제공한다.In addition, the present invention provides a health functional food composition for preventing and improving gastrointestinal diseases containing the compound represented by Formula 1, its isomers or salts thereof as an active ingredient.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 염을 유효성분으로 함유하는 위장 질환의 예방 및 개선용 식품 조성물을 제공한다.In addition, the present invention provides a food composition for preventing and improving gastrointestinal diseases containing the compound represented by Formula 1, an isomer thereof, or a salt thereof as an active ingredient.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 헬리코박터 파이로리 균의 감염 또는 증식 억제용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for inhibiting the infection or growth of Helicobacter pylori bacteria containing the compound represented by Formula 1, its isomers or pharmaceutically acceptable salts thereof as an active ingredient.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 헬리코박터 파이로리 균의 감염 또는 증식 억제용 건강기능식품 조성물을 제공한다.In addition, the present invention provides a health functional food composition for inhibiting the infection or growth of Helicobacter pylori bacteria, which contains the compound represented by Formula 1, its isomers or pharmaceutically acceptable salts thereof as an active ingredient.
아울러, 본 발명은 상기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 염을 유효성분으로 함유하는 헬리코박터 파이로리 균의 감염 또는 증식 억제용 식품 조성물을 제공한다.In addition, the present invention provides a food composition for inhibiting the infection or growth of Helicobacter pylori bacteria containing the compound represented by Formula 1, an isomer thereof, or a salt thereof as an active ingredient.
본 발명에 따른 화합물은 그람음성균인 H.pylori에 탁월하고 유효한 항균효과를 가져 위암 발생률을 낮추고 위염억제에 효과적이며, 생체이용률이 높고, 독성이 낮으며, 대량 생산이 용이하여 위염, 위점막 손상, 위궤양, 위궤양 장염, 십이지장궤양, 위암 또는 급성 위장관 출혈 등의 위장 관련 질환의 예방, 개선 또는 치료에 유용하게 사용할 수 있다.The compound according to the present invention has an excellent and effective antibacterial effect against Gram-negative bacteria, H.pylori , lowers the incidence of gastric cancer, is effective in suppressing gastritis, has high bioavailability, low toxicity, and is easy to mass-produce, thereby preventing gastritis and gastric mucosal damage. , It can be usefully used for the prevention, improvement, or treatment of gastric-related diseases such as gastric ulcer, gastric ulcer enteritis, duodenal ulcer, gastric cancer, or acute gastrointestinal bleeding.
도 1은 본 발명에 따른 화학식 1의 화합물의 H.pylori에 대한 항균 시험으로서 디스크확산법으로 지름환을 측정한 결과를 보여주는 그림이다.
도 2는 본 발명에 따른 화학식 1의 화합물의 H.pylori에 대한 항균 시험으로서 고체배지 희석법으로 최소살균농도(minimum bactericidal concentration, MBC)를 측정한 결과를 보여주는 그림이다.
도 3은 본 발명에 따른 화학식 1의 화합물의 H.pylori에 대한 항균 시험으로서 액체배지 희석법으로 최소저해농도(minimum inhibitory concentration, MIC)를 측정한 결과를 보여주는 그림이다.1 is a picture showing the results of measuring the ring diameter by the disk diffusion method as an antibacterial test for H. pylori of the compound of
Figure 2 is a picture showing the results of measuring the minimum bactericidal concentration (MBC) by the solid medium dilution method as an antibacterial test for H. pylori of the compound of
Figure 3 is a picture showing the results of measuring the minimum inhibitory concentration (MIC) by liquid medium dilution method as an antibacterial test for H. pylori of the compound of
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명은 하기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 위장 질환의 예방 및 치료용 약학적 조성물을 제공한다:The present invention provides a pharmaceutical composition for preventing and treating gastrointestinal diseases containing a compound represented by Formula 1, an isomer thereof or a pharmaceutically acceptable salt thereof as an active ingredient:
[화학식 1][Formula 1]
상기 조성물은 헬리코박터 파이로리(Helicobacter pylori)균의 증식을 억제하는 활성을 가진다.The composition has an activity of inhibiting the proliferation of Helicobacter pylori bacteria.
상기 조성물은 상기 화합물을 조성물 총 중량을 기준으로 0.0001 ~ 10 중량%의 양으로 함유할 수 있고, 조성물 총 중량을 기준으로 0.001 ~ 1 중량%의 양으로 함유할 수 있다.The composition may contain the compound in an amount of 0.0001 to 10% by weight based on the total weight of the composition, and may be contained in an amount of 0.001 to 1% by weight based on the total weight of the composition.
상기 "이성질체"는 특히 광학 이성질체(예를 들어 필수적으로 순수한 거울상 이성질체(enantiomer), 필수적으로 순수한 부분 입체이성질체(diastereomer), 및 이들의 혼합물) 뿐 아니라, 구조 이성질체(즉, 하나 이상의 화학 결합의 각도에만 차이가 있는 이성질체), 위치 이성질체(특히, 호변 이성질체(tautomer)) 및 기하 이성질체(예를 들어, 시스-트랜스 이성질체)를 모두 포함하는 의미이다.The "isomer" refers in particular to optical isomers (e.g., essentially pure enantiomers, essentially pure diastereomers, and mixtures thereof) as well as structural isomers (i.e., the angle of one or more chemical bonds). Isomers differing only in), positional isomers (particularly, tautomers), and geometric isomers (eg, cis-trans isomers) are meant to be included.
예를 들어, 거울상 이성질체 및 입체이성질체와 관련된 "필수적으로 순수한"은 구체적인 화합물, 예를 들어 약 90% 이상, 바람직하게 약 95% 이상, 더욱 바람직하게 약 97% 이상, 더욱 바람직하게 약 98% 이상, 더욱 바람직하게 약 99% 이상, 더욱 바람직하게 약 99.5% (w/w)의 거울상 이성질체 또는 입체이성질체를 의미한다.For example, "essentially pure" in relation to enantiomers and stereoisomers refers to a specific compound, e.g., about 90% or greater, preferably about 95% or greater, more preferably about 97% or greater, even more preferably about 98% or greater. , more preferably about 99% or more, more preferably about 99.5% (w/w) of enantiomers or stereoisomers.
상기 "약학적으로 허용 가능한 염"은 약학적으로 허용 가능한 본 발명에 따른 화합물의 염을 의미하며, 모화합물의 목적하는 약성을 보유한다. 이러한 염은 (1) 염화수소산, 브롬화수소산, 황산, 질산, 인산 등과 같은 무기산에 의해 형성된 산 부가염; 또는 아세트산, 프로피온산, 헥산산, 사이클로펜탄프로피온산, 글리콜산, 피루빈산, 젖산, 말론산, 숙신산, 말산, 말레산, 푸마르산, 타르타르산, 구연산, 벤조산, 3-(4-하이드록시벤조일)벤조산, 신남산(cinnamic acid), 만델린산(mandelic acid), 메탄설폰산, 에탄설폰산, 1,2-에탄-디설폰산, 2-하이드록시에탄설폰산, 벤젠설폰산, 4-클로로벤젠설폰산, 2-나프탈렌설폰산, 4-톨루엔설폰산, 캄포술폰산(camphorsulfonic acid), 4-메틸바이사이클로 [2.2.2]-옥트-2-엔-1-카르복시산, 글루코헵톤 산(glucoheptonic acid), 3-페닐프로피온산, 트리메틸아세트산, 터셔리 부틸아세트산, 라우릴 황산, 글루콘산, 글루탐산, 하이드록시나프토산(hydroxynaphthoic acid), 살리실산, 스테아르산, 뮤코닉산(muconic acid) 등과 같은 유기산에 의해 형성된 산 부가염; 또는 (2) 모화합물에 존재하는 산성 양성자가 치환되는 경우 형성되는 염을 포함한다.The "pharmaceutically acceptable salt" means a pharmaceutically acceptable salt of the compound according to the present invention, and possesses the desired medicinal properties of the parent compound. These salts include (1) acid addition salts formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like; or acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl)benzoic acid, Cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 4-chlorobenzenesulfonic acid , 2-naphthalenesulfonic acid, 4-toluenesulfonic acid, camphorsulfonic acid, 4-methylbicyclo[2.2.2]-oct-2-ene-1-carboxylic acid, glucoheptonic acid, 3 -Acid addition formed by organic acids such as phenylpropionic acid, trimethylacetic acid, tertiary butylacetic acid, lauryl sulfate, gluconic acid, glutamic acid, hydroxynaphthoic acid, salicylic acid, stearic acid, muconic acid, etc. salt; or (2) a salt formed when an acidic proton present in the parent compound is substituted.
상기 "예방"은 질병 또는 질환의 획득 위험을 감소시키는 것을 의미한다(즉, 하나 이상의 질병에 대한 임상적 징후가 개체에서 발달하지 않도록 유도하는 것으로, 질병이 노출 또는 예치될 수 있으나, 아직 질병의 징후들을 경험하지 않거나 또는 노출되지 않는 것이다).The "prevention" means reducing the risk of acquiring a disease or condition (i.e., inducing clinical signs of one or more diseases to not develop in a subject, to which the disease may be exposed or deposited, but not yet of the disease). not experiencing or not being exposed to symptoms).
상기 조성물은 상기 화합물을 예방 또는 치료에 유효한 양으로 포함할 수 있다. The composition may contain the compound in an amount effective for prophylaxis or treatment.
상기 "유효한 양"은 질병을 개선 또는 치료하기 위하여 개체에 투여하는 경우, 화합물의 양이 질병에 대한 예방, 개선 또는 치료 효과를 내기에 충분한 것을 의미한다. 상기 "유효한 양"은 질병과 질병의 심각도 및 치료받는 개체의 연령 및 체중 등에 따라 다양할 수 있다.The "effective amount" means that when administered to a subject to improve or treat a disease, the amount of the compound is sufficient to produce a preventive, ameliorative or therapeutic effect on the disease. The "effective amount" may vary depending on the disease, the severity of the disease, and the age and weight of the individual being treated.
상기 조성물은 약학적으로 허용 가능한 담체를 더 포함할 수 있다.The composition may further include a pharmaceutically acceptable carrier.
상기 "약학적으로 허용 가능한 담체"는 본 발명에 따른 화합물과 함께 희석제, 보조제, 부형제 또는 담체가 투여됨을 의미한다.The "pharmaceutically acceptable carrier" means that a diluent, adjuvant, excipient or carrier is administered together with the compound according to the present invention.
예를 들어, 본 발명의 화합물은 오일, 프로필렌 글리콜 또는 통상 사용되는 기타 용매 중에 용해되어 주사제로 제조될 수 있다. 담체의 적합한 예에는 생리적 염류 용액 (physiological saline), 폴리에틸렌글리콜, 에탄올, 식물성 오일, 이소프로필 미리스테이트(isopropyl myristate)등이 포함되나, 이에 제한되지 않는다. 국소 투여를 위해, 본 발명의 화합물들은 연고 또는 크림 형태로 제형화될 수 있다.For example, the compound of the present invention can be prepared as an injection by dissolving in oil, propylene glycol or other commonly used solvents. Suitable examples of the carrier include, but are not limited to, physiological saline, polyethylene glycol, ethanol, vegetable oil, isopropyl myristate, and the like. For topical administration, the compounds of the present invention may be formulated in ointment or cream form.
상기 조성물은 단독 또는 다른 약제학적 활성 화합물과 혼합하여 사용될 수 있다.The composition may be used alone or in admixture with other pharmaceutically active compounds.
상기 조성물은 식염수 및 5% 덱스트로스와 같은 수용성 용매 또는 식물성 오일, 합성 지방산 글리세리드, 더 높은 정도의 지방산 에스테르 및 프로필렌 글리콜과 같은 수불용성 용매 중에 용해, 현탁 또는 유화하여 주사제로 제형화될 수 있다. 본 발명의 제형들은 용해제, 등장화제, 현탁화제(suspending agent), 유화제(emulsifier), 안정화제 및 보존제와 같은 통상의 어떠한 첨가제라도 포함할 수 있다.The composition can be formulated as an injectable by dissolving, suspending or emulsifying in water-soluble solvents such as saline and 5% dextrose or in water-insoluble solvents such as vegetable oils, synthetic fatty acid glycerides, higher degree fatty acid esters and propylene glycol. The formulations of the present invention may contain any conventional additives such as solubilizers, tonicity agents, suspending agents, emulsifiers, stabilizers and preservatives.
상기 조성물의 바람직한 투여량은 환자의 상태 및 체중을, 특정 질환의 심각성, 투약 형태 및 경로와 투여 기간을 포함하여 다양한 요소에 따라 달라질 수 있으나, 당업자는 적절하게 선택할 수 있다. 바람직하게 일당 체중의 0.001 내지 100 mg/kg 범위의 양으로, 더욱 바람직하게 일당 체중의 0.01 내지 30 mg/kg 범위의 양으로 투여될 수 있다. 투여량은 일당 1회, 또는 각각 나누어진 부분과 함께 1일 수회로 투여될 수 있다. 본 발명의 화합물은 약학 조성물에서 조성물의 총량을 기준으로 0.0001~10 중량%, 바람직하게 0.001~1 중량%의 양으로 사용된다.The preferred dosage of the composition may vary depending on various factors, including the patient's condition and body weight, the severity of a particular disease, dosage form and route and administration period, but those skilled in the art can appropriately select it. It may be preferably administered in an amount ranging from 0.001 to 100 mg/kg of body weight per day, more preferably in an amount ranging from 0.01 to 30 mg/kg of body weight per day. The dosage can be administered once per day or several times per day with each divided portion. The compound of the present invention is used in the pharmaceutical composition in an amount of 0.0001 to 10% by weight, preferably 0.001 to 1% by weight, based on the total amount of the composition.
상기 조성물은 임상투여 시에 다양한 하기의 경구 또는 비경구 투여 형태로 제제화되어 투여될 수 있으나, 이에 한정되는 것은 아니다. The composition may be formulated and administered in various oral or parenteral dosage forms at the time of clinical administration, but is not limited thereto.
상기 경구 투여용 제형으로는 예를 들면 정제, 환제, 경/연질 캅셀제, 액제, 현탁제, 유화제, 시럽제, 과립제, 엘릭시르제 등이 있는데, 이들 제형은 유효성분 이외에 희석제(예: 락토즈, 덱스트로즈, 수크로즈, 만니톨, 솔비톨, 셀룰로즈 및/ 또는 글리신), 활택제(예: 실리카, 탈크, 스테아르산 및 그의 마그네슘 또는 칼슘염 및/또는 폴리에틸렌 글리콜)를 함유하고 있다. 정제는 또한 마그네슘 알루미늄 실리케이트, 전분 페이스트, 젤라틴, 메틸셀룰로즈, 나트륨 카복시메틸셀룰로즈 및/또는 폴리비닐피롤리딘과 같은 결합제를 함유할 수 있으며, 경우에 따라 전분, 한천, 알긴산 또는 그의 나트륨 염과 같은 붕해제 또는 비등 혼합물 및/또는 흡수제, 착색제, 향미제, 및 감미제를 함유할 수 있다.Formulations for oral administration include, for example, tablets, pills, hard/soft capsules, solutions, suspensions, emulsifiers, syrups, granules, elixirs, etc. trorose, sucrose, mannitol, sorbitol, cellulose and/or glycine), lubricants (eg silica, talc, stearic acid and its magnesium or calcium salts and/or polyethylene glycol). Tablets may also contain binders such as magnesium aluminum silicate, starch paste, gelatin, methylcellulose, sodium carboxymethylcellulose and/or polyvinylpyrrolidine, optionally starch, agar, alginic acid or its sodium salt. may contain disintegrants or effervescent mixtures and/or absorbents, colorants, flavors, and sweeteners.
상기 비경구 투여 제형으로는 피하주사, 정맥주사, 근육 내 주사 또는 흉부 내 주사를 주입하는 주사제 등이 있다. 이때, 비경구 투여용 제형으로 제제화하기 위하여 상기 화합물을 안정제 또는 완충제와 함께 물에 혼합하여 용액 또는 현탁액으로 제조하고, 이를 앰플 또는 바이알 단위 투여형으로 제조할 수 있다. 상기 조성물은 멸균되고/되거나 방부제, 안정화제, 수화제 또는 유화 촉진제, 삼투압 조절을 위한 염 및/또는 완충제 등의 보조제, 및 기타 치료적으로 유용한 물질을 함유할 수 있다.Examples of the parenteral dosage form include injections for subcutaneous injection, intravenous injection, intramuscular injection, or intrathoracic injection. At this time, in order to formulate a formulation for parenteral administration, the compound may be mixed with water along with a stabilizer or buffer to prepare a solution or suspension, which may be prepared in an ampoule or vial unit dosage form. The composition may be sterile and/or contain adjuvants such as preservatives, stabilizers, hydration or emulsification accelerators, salts and/or buffers for osmotic pressure control, and other therapeutically useful substances.
상기 위장 질환은 위염, 위점막 손상, 위점막의 미란, 출혈, 발적 및 부종, 위궤양, 위궤양 장염, 역류성식도염, 십이지장염, 십이지장궤양, 위암 및 급성 위장관 출혈로 구성된 군으로부터 선택되는 어느 하나 이상일 수 있다.The gastrointestinal disease may be any one or more selected from the group consisting of gastritis, gastric mucosal damage, gastric mucosal erosion, hemorrhage, redness and edema, gastric ulcer, gastric ulcerative colitis, reflux esophagitis, duodenitis, duodenal ulcer, gastric cancer, and acute gastrointestinal bleeding. there is.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 염을 유효성분으로 함유하는 위장 질환의 예방 및 개선용 건강기능식품 조성물을 제공한다.In addition, the present invention provides a health functional food composition for preventing and improving gastrointestinal diseases containing the compound represented by
상기 조성물은 헬리코박터 파이로리(Helicobacter pylori)균의 증식을 억제하는 활성을 가진다.The composition has an activity of inhibiting the proliferation of Helicobacter pylori bacteria.
상기 조성물은 상기 화합물을 조성물 총 중량을 기준으로 0.0001 ~ 10 중량%의 양으로 함유할 수 있고, 조성물 총 중량을 기준으로 0.001 ~ 1 중량%의 양으로 함유할 수 있다.The composition may contain the compound in an amount of 0.0001 to 10% by weight based on the total weight of the composition, and may be contained in an amount of 0.001 to 1% by weight based on the total weight of the composition.
상기 위장 질환은 위염, 위점막 손상, 위점막의 미란, 출혈, 발적 및 부종, 위궤양, 위궤양 장염, 역류성식도염, 십이지장염, 십이지장궤양, 위암 및 급성 위장관 출혈로 구성된 군으로부터 선택되는 어느 하나 이상일 수 있다.The gastrointestinal disease may be any one or more selected from the group consisting of gastritis, gastric mucosal damage, gastric mucosal erosion, hemorrhage, redness and edema, gastric ulcer, gastric ulcerative colitis, reflux esophagitis, duodenitis, duodenal ulcer, gastric cancer, and acute gastrointestinal bleeding. there is.
상기 건강기능식품 조성물은 건강기능식품에 관한 법률 제6722호에 따른 인체에 유용한 기능성을 가진 원료나 성분을 사용하여 제조 및 가공한 식품을 의미하며, 인체의 구조 및 기능에 대하여 영양소를 조절하거나 생리학적 작용 등과 같은 보건 용도에 유용한 효과를 얻을 목적으로 섭취하는 식품을 의미한다.The health functional food composition refers to a food manufactured and processed using raw materials or ingredients having useful functionalities for the human body in accordance with the Health Functional Food Act No. 6722, and regulates nutrients for the structure and function of the human body or physiological It refers to food consumed for the purpose of obtaining useful effects for health purposes, such as medical action.
상기 건강기능식품 조성물은 당해 기술분야에 공지되어 있는 통상적인 건강기능식품의 제형으로 제제화될 수 있고, 과립제, 정제, 환제, 현탁액, 에멀젼, 시럽제, 드링크제 등으로 제조될 수 있으며, 상기 건강기능식품의 종류에는 특별한 제한이 없다.The health functional food composition may be formulated into a conventional health functional food formulation known in the art, and may be prepared as granules, tablets, pills, suspensions, emulsions, syrups, drinks, etc., and the health functional food There is no particular limitation on the type of
상기 건강기능식품 조성물은 유효성분 이외에 식품학적으로 허용 가능한 첨가제를 포함할 수 있고, 예로는 여러 가지 영양제, 비타민, 광물(전해질), 합성 풍미제 및 천연 풍미제 등의 풍미제, 착색제 및 충진제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산화제 등이 포함되지만, 이에 제한되는 것은 아니다.The health functional food composition may include food-acceptable additives in addition to active ingredients, examples of which include various nutrients, vitamins, minerals (electrolytes), flavors such as synthetic flavors and natural flavors, colorants and fillers, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, carbonating agents, and the like.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 염을 유효성분으로 함유하는 위장 질환의 예방 및 개선용 식품 조성물을 제공한다.In addition, the present invention provides a food composition for preventing and improving gastrointestinal diseases containing the compound represented by
상기 조성물은 헬리코박터 파이로리(Helicobacter pylori)균의 증식을 억제하는 활성을 가진다.The composition has an activity of inhibiting the proliferation of Helicobacter pylori bacteria.
상기 위장 질환은 위염, 위점막 손상, 위점막의 미란, 출혈, 발적 및 부종, 위궤양, 위궤양 장염, 역류성식도염, 십이지장염, 십이지장궤양, 위암 및 급성 위장관 출혈로 구성된 군으로부터 선택되는 어느 하나 이상일 수 있다.The gastrointestinal disease may be any one or more selected from the group consisting of gastritis, gastric mucosal damage, gastric mucosal erosion, hemorrhage, redness and edema, gastric ulcer, gastric ulcerative colitis, reflux esophagitis, duodenitis, duodenal ulcer, gastric cancer, and acute gastrointestinal bleeding. there is.
상기 식품 조성물의 종류에는 특별한 제한은 없다. 식품의 예로는 육류, 소시지류, 빵류, 초콜릿류, 캔디류, 스넥류, 과자류, 피자, 라면, 면류, 껌류, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 차, 드링크제, 알코올음료 및 비타민 복합제 등이 있으며, 통상적인 의미에서의 건강식품을 모두 포함한다.There is no particular limitation on the type of the food composition. Examples of food include meat, sausages, breads, chocolates, candies, snacks, confectionery, pizza, ramen, noodles, chewing gum, dairy products including ice cream, various soups, beverages, tea, drinks, alcoholic beverages and vitamin complexes, etc. This includes all health foods in the usual sense.
상기 식품 조성물은 여러 가지 향미제 또는 천연 탄수화물 등을 추가 성분으로서 함유할 수 있고, 여러 가지 영양제, 비타민, 전해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알코올, 탄산음료에 사용되는 탄산화제 등을 함유할 수 있다. 이러한 첨가제의 비율은 크게 중요하진 않지만 식품 조성물 100 중량부당 0.01 ~ 0.1 중량부의 범위에서 선택되는 것이 일반적이다.The food composition may contain various flavors or natural carbohydrates as additional components, various nutrients, vitamins, electrolytes, flavors, colorants, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloids It may contain thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohol, carbonation agents used in carbonated beverages, and the like. The ratio of these additives is not very important, but is generally selected in the range of 0.01 to 0.1 parts by weight per 100 parts by weight of the food composition.
또한, 본 발명은 하기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 헬리코박터 파이로리 균의 감염 또는 증식 억제용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for inhibiting the infection or growth of Helicobacter pylori bacteria, containing a compound represented by
[화학식 1][Formula 1]
또한, 본 발명은 상기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 염을 유효성분으로 함유하는 헬리코박터 파이로리 균의 감염 또는 증식 억제용 건강기능식품 조성물을 제공한다.In addition, the present invention provides a health functional food composition for inhibiting infection or growth of Helicobacter pylori bacteria, which contains the compound represented by
아울러, 본 발명은 상기 화학식 1로 표시되는 화합물, 이의 이성질체 또는 이들의 염을 유효성분으로 함유하는 헬리코박터 파이로리 균의 감염 또는 증식 억제용 식품 조성물을 제공한다.In addition, the present invention provides a food composition for inhibiting the infection or growth of Helicobacter pylori bacteria containing the compound represented by
이하, 하기 실시예 및 실험예를 통해 본 발명을 더욱 구체적으로 상술한다. 그러나 하기 실시예 및 실험예는 본 발명을 예시하기 위한 것이며, 본 발명의 범주가 이들만으로 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail through the following examples and experimental examples. However, the following Examples and Experimental Examples are intended to illustrate the present invention, and the scope of the present invention is not limited only to these.
<실시예 1> 화학식 1의 화합물의 합성 <Example 1> Synthesis of Compound of
대한민국 등록특허 제10-2022323호의 <실시예 7> 및 <실시예 12>에 기재된 방법에 따라 화학식 1의 화합물인 N2,N2-bis(3-aminopropyl)-N4,N6-bis(naphthalen-1-ylmethyl)-1,3,5-triazine-2,4,6-triamine [Chemical Formula: C31H36N8, Molecular Weight: 520.6711]을 합성하였다. According to the methods described in <Example 7> and <Example 12> of Korean Patent Registration No. 10-2022323, N 2 ,N 2 -bis(3-aminopropyl)-N 4 ,N 6 -bis( naphthalen-1-ylmethyl)-1,3,5-triazine-2,4,6-triamine [Chemical Formula: C 31 H 36 N 8 , Molecular Weight: 520.6711] was synthesized.
이하, 합성된 화학식 1의 화합물을 "PCN1905"로 나타내었다. Hereinafter, the synthesized compound of
<실험예 1> 디스크 확산법(Disc diffusion method) 분석<Experimental Example 1> Disc diffusion method analysis
멸균된 paper disc (φ 6 mm)에 0.45 μm membrane filter (Sigma Chemical Co., St. Louis, MO)로 여과한 추출물을 vacuum evaporator로 농축한 후 멸균수로 희석하여 phenol 함량이 5 ~ 20 μg/10 μL가 되도록 조절한 상기 PCN1905를 10 μL를 paper disc에 흡수시켰다. 대조군으로 PCN1905 대신 용매인 멸균수를 흡수시킴. Disc paper는 37℃ 배양기에서 3 ~ 5시간 동안 건조하여 용매를 제거하였다.The extract filtered with a 0.45 μm membrane filter (Sigma Chemical Co., St. Louis, MO) on a sterilized paper disc (φ 6 mm) was concentrated with a vacuum evaporator and diluted with sterile water to obtain a phenol content of 5 to 20 μg/ml. 10 μL of the PCN1905 adjusted to be 10 μL was absorbed onto a paper disc. As a control, sterilized water as a solvent was absorbed instead of PCN1905. Disc paper was dried in a 37°C incubator for 3 to 5 hours to remove the solvent.
배양한 H.pylori 균의 집락을 취하여 멸균 생리식염수로 옮겨 각각의 균수를 McFarland 탁도 2 (6 X 108/mL)를 맞추어 세균 부유액을 준비하였다. 10% fetal bovine serum이 포함된 Mueller-Hinton agar 표면에 세균 부유액 100 μL를 분주하여 멸균된 면봉으로 3회 반복하여 도말하였다.Colonies of cultured H.pylori bacteria were taken and transferred to sterile physiological saline, and a bacterial suspension was prepared by adjusting the number of bacteria to McFarland turbidity 2 (6 X 10 8 /mL). 100 μL of the bacterial suspension was dispensed on the surface of Mueller-Hinton agar containing 10% fetal bovine serum and smeared three times with a sterile cotton swab.
PCN1905가 흡수된 paper disc를 H.pylori 균을 도말한 배지에 올려놓고 밀착시켰다. 37℃에서 72 ~ 120시간 동안 배양한 후 disc 주변에 생성된 생육저해환(clear zone)의 지름을 측정하였다. The paper disc on which PCN1905 was absorbed was placed on the H.pylori- smeared medium and adhered closely. After incubation at 37°C for 72 to 120 hours, the diameter of the clear zone generated around the disc was measured.
그 결과, 도 1에 나타난 바와 같이 PCN1905가 H.pylori 균에 대해 우수한 항균 활성을 가지는 것을 알 수 있었다(도 1).As a result, as shown in FIG. 1, it was found that PCN1905 has excellent antibacterial activity against H. pylori bacteria (FIG. 1).
<실험예 2> 고체배지 희석법(Agar dilution method) 분석<Experimental Example 2> Solid medium dilution method (Agar dilution method) analysis
농도별(2배 단계 희석) PCN1905와 10% fetal bovine serum이 포함된 Mueller-Hinton agar를 제작하였다. 대조군 배지에는 최고 농도와 동일한 용매의 양을 첨가하여 제작하였다. 배양된 H. pylori 균의 집락을 취하여 McFarland 탁도 2 (6 X 108 CFU/mL)가 되도록 멸균 생리식염수에 세균 부유액을 준비하였다. 제작한 배지 표면에 세균 부유액 10 μL를 분주한 뒤 미호기성의 37℃ 배양기에서 배양하였다. 72시간 후, 세균의 성장 유무를 육안으로 확인하였다.Mueller-Hinton agar containing PCN1905 and 10% fetal bovine serum by concentration (2-fold dilution) was prepared. The control medium was prepared by adding the same amount of solvent as the highest concentration. Colonies of the cultured H. pylori were taken and a bacterial suspension was prepared in sterile physiological saline to have a McFarland turbidity of 2 (6 X 10 8 CFU/mL). After dispensing 10 μL of the bacterial suspension on the surface of the prepared medium, it was cultured in a microaerobic 37°C incubator. After 72 hours, the presence or absence of bacterial growth was visually confirmed.
그 결과, 도 2에 나타난 바와 같이 최소살균농도(minimum bactericidal concentration, MBC)가 6.25 uM인 것을 알 수 있었다(도 2).As a result, as shown in FIG. 2, it was found that the minimum bactericidal concentration (MBC) was 6.25 uM (FIG. 2).
<실험예 3> 액체배지 희석법(Broth dilution method) 분석<Experimental Example 3> Broth dilution method analysis
배양된 H. pylori 균의 집락을 취하여 각각의 균수를 최종 1 X 108/mL가 되도록 10% fetal bovine serum이 포함된 Mueller-Hinton broth에 세균 부유액을 준비하였다. PCN1905의 농도는 고체배지 희석법의 결과를 참조하여 적절한 농도 범위를 설정하여 Mueller-Hinton broth에 단계적으로 희석하였다. 대조군은 실험군의 최고 농도와 동일한 용매의 양이 되도록 하였다. 농도별 PCN1905와 세균 부유액을 96 well plate에 각각 100 μL씩 분주한 후 미호기성의 37℃ 배양기에서 72시간 배양하였다. 최소저해농도(minimum inhibitory concentration, MIC)는 UV-spectrophotometer를 이용하여 600 nm에서의 흡광도를 측정하여 균의 저해가 일어나는 최소 농도로 결정하였다.Colonies of cultured H. pylori were taken, and a bacterial suspension was prepared in Mueller-Hinton broth containing 10% fetal bovine serum so that the final number of each was 1 X 10 8 /mL. The concentration of PCN1905 was gradually diluted in Mueller-Hinton broth by setting an appropriate concentration range with reference to the results of the solid medium dilution method. The control group was made to have the same amount of solvent as the highest concentration of the experimental group. After dispensing 100 μL each of PCN1905 and bacterial suspension for each concentration into a 96 well plate, they were incubated for 72 hours in a microaerobic 37℃ incubator. The minimum inhibitory concentration (MIC) was determined by measuring the absorbance at 600 nm using a UV-spectrophotometer to determine the minimum concentration at which inhibition of bacteria occurs.
그 결과, 도 3에 나타난 바와 같이 최소저해농도가 3.13 uM인 것을 알 수 있었다(도 3).As a result, as shown in FIG. 3, it was found that the minimum inhibitory concentration was 3.13 uM (FIG. 3).
Claims (9)
[화학식 1]
A pharmaceutical composition for preventing and treating gastric mucosal damage caused by Helicobacter pylori containing a compound represented by Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient:
[Formula 1]
상기 조성물은 상기 화합물을 조성물 총 중량을 기준으로 0.001 ~ 1 중량%의 양으로 함유되는 것을 특징으로 하는 헬리코박터 파이로리 균에 의해 유발된 위점막 손상 예방 및 치료용 약학적 조성물.
According to claim 1,
The composition is a pharmaceutical composition for preventing and treating gastric mucosal damage caused by Helicobacter pylori, characterized in that the compound is contained in an amount of 0.001 to 1% by weight based on the total weight of the composition.
[화학식 1]
A health functional food composition for preventing and improving gastric mucosal damage caused by Helicobacter pylori containing a compound represented by Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient:
[Formula 1]
[화학식 1]
A food composition for preventing and improving gastric mucosal damage caused by Helicobacter pylori bacteria represented by Formula 1 below or containing a pharmaceutically acceptable salt thereof as an active ingredient:
[Formula 1]
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