KR20050023998A - Peptic ulcer healing agent - Google Patents
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- KR20050023998A KR20050023998A KR1020030061791A KR20030061791A KR20050023998A KR 20050023998 A KR20050023998 A KR 20050023998A KR 1020030061791 A KR1020030061791 A KR 1020030061791A KR 20030061791 A KR20030061791 A KR 20030061791A KR 20050023998 A KR20050023998 A KR 20050023998A
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Abstract
Description
[발명이 속하는 기술분야][TECHNICAL FIELD OF THE INVENTION]
본 발명은 소화성 궤양 치료제에 관한 것으로, 보다 상세하게는 프로톤 펌프를 효과적으로 억제할 수 있는 유효화합물을 주성분으로 포함하는 위산억제제 및 소화성 궤양 치료제에 관한 것이다.The present invention relates to a peptic ulcer therapeutic agent, and more particularly to a gastric acid inhibitor and a peptic ulcer therapeutic agent containing an active compound capable of effectively inhibiting the proton pump.
[종래기술][Private Technology]
소화성 궤양은 위장관벽의 점막이 위액으로 소화되어 궤양을 일으킨 상태를 통틀어 일컫는 것으로서, 위궤양과 십이지장궤양이 대표적이다. 위장관점막은 위산과 같은 강력한 소화액과 접촉하고 있기 때문에, 위산과 같이 공격인자에 대하여 견뎌낼 수 있는 방어인자가 잘 발달해 있다. 공격인자보다 방어인자가 강하거나 균형을 이루고 있으면 궤양이 생기지 않지만, 공격인자가 정상보다 강해지거나 방어인자가 약해지면 소화성 궤양이 생긴다. Peptic ulcer refers to a state in which the mucous membrane of the gastrointestinal wall is digested with gastric juice, causing ulcers, and gastric ulcer and duodenal ulcer are typical. Since the gastrointestinal mucosa is in contact with strong digestive fluids such as gastric acid, there is a well-developed defensive factor that can withstand attack agents such as gastric acid. If the defender is stronger or balanced than the attacker, no ulceration occurs, but if the attacker is stronger than normal or the defender is weaker, a peptic ulcer occurs.
이에 따라, 소화성 궤양 치료제의 개발은 공격인자를 제어하고, 방어인자를 강화하는 두 가지 측면으로 나눌 수 있다. 그 중에서도 특히 소화성 궤양 치료제의 개발은 공격인자를 제어하는 측면에 초점을 두어 발달해 왔다. 공격인자를 제어하는 대표적인 치료제의 개발은 위산을 중화시키는 제산제(anti-acid) 개발을 시작으로 하여, 항콜린성 약물(anti-choline), 및 잔탁으로 널리 알려진 H2 수용체 길항제(H2 receptor antagonist)의 개발로 이어져서, 현재에는 프로톤펌프 저해제(proton pump inhibitor)인 오메프라졸(Omeprazole)의 개발에 이르고 있다. Accordingly, the development of a peptic ulcer therapeutic agent can be divided into two aspects of controlling attack factors and strengthening defense factors. In particular, the development of peptic ulcer drugs has been developed with a focus on controlling attack factors. The development of representative therapeutic agents to control attack factors begins with the development of anti-acids that neutralize gastric acid, leading to the development of anticholinergic drugs, and H2 receptor antagonists, also known as residues. This led to the development of omeprazole, a proton pump inhibitor.
상기 오메프라졸은 소화성 궤양 치료에 우수한 효과를 나타낸다고 알려져 있다. 그러나, 산성조건에서 불안정하고, 비가역적인 장기 위산 분비를 저하시켜 위암을 발병하게 할 수도 있다는 문제점이 있다. 또한, 간에 존재하는 여러 산화효소의 작용을 저해하여 간에 손상을 입힐 수도 있으며, 드물게는 과민성을 나타낸다는 문제점이 있다.The omeprazole is known to exert an excellent effect in the treatment of peptic ulcer. However, it is unstable under acidic conditions, There is a problem that the cancer can be caused by lowering the irreversible long-term gastric acid secretion. In addition, the liver may be damaged by inhibiting the action of various oxidases present in the liver, and rarely, there is a problem of hypersensitivity.
이에 따라, 발암과 같은 부작용이 적어 인체에 안전하면서도 약리작용이 우수한 소화성 궤양 치료제에 대한 개발이 요구되는 실정이다. Accordingly, there is a need for the development of a peptic ulcer therapeutic agent that is safe for the human body and has excellent pharmacological effects due to fewer side effects such as carcinogenesis.
상기 종래기술의 문제점을 해결하기 위하여 안출된 것으로서, 본 발명은 프로톤 펌프 저해제로 작용하여 위산분비를 억제시킬 수 있는 화합물을 제공하는 목적으로 한다.In order to solve the problems of the prior art, the present invention is to provide a compound that can act as a proton pump inhibitor to suppress gastric acid secretion.
또한 본 발명은 프로톤 펌프 저해제로 작용하여 위산분비를 억제시킬 수 있는 화합물을 포함하는 위산분비 억제제 및 소화성 궤양 치료제를 제공하는 것을 목적으로 한다.It is another object of the present invention to provide a gastric acid secretion inhibitor and a peptic ulcer therapeutic agent comprising a compound capable of inhibiting gastric acid secretion by acting as a proton pump inhibitor.
상기 목적을 달성하기 위하여, 본 발명은 아아데노신, 아피올레, 부틸리덴네프탈라이드, 부틸프탈라이드, 클로로제닌산, 스니딜라이드, 코니페릴 페룰레이트, 페룰린산, 리구스틸라이드, 리구스틸리디올, 네오스니딜라이드, 프레그네노놀, 센키우놀라이드, 센키우놀라이드 B, 센키우놀라이드 C, 센키우놀라이드 D, 센키우놀라이드 F, 센키우놀라이드 G, 센키우놀라이드 H, 센키우놀라이드 I, 센키우놀라이드 J, 바닐린, 비타민 C로 이루어진 군으로부터 1종이상 선택된 화합물을 유효성분으로 포함하는 위산분비 억제용 조성물을 제공한다.In order to achieve the above object, the present invention provides adenosine, apiole, butylidene phthalide, butylphthalide, chlorogeninic acid, snidylide, coniferyl ferulate, ferulic acid, ligustilide, ligustilidiol , Neosnilide, pregnenool, senkiunolide, senkiunolide B, senkiunolide C, senkiunolide D, senkiunolide F, senkiunolide G, senkiunolide H, It provides a composition for inhibiting gastric acid secretion comprising at least one compound selected from the group consisting of senkiunolide I, senkiunolide J, vanillin, vitamin C as an active ingredient.
또한 본 발명은 아데노신, 아피올레, 부틸리덴네프탈라이드, 부틸프탈라이드, 클로로제닌산, 스니딜라이드, 코니페릴 페룰레이트, 페룰린산, 리구스틸라이드, 리구스틸리디올, 네오스니딜라이드, 프레그네노놀, 센키우놀라이드, 센키우놀라이드 B, 센키우놀라이드 C, 센키우놀라이드 D, 센키우놀라이드 F, 센키우놀라이드 G, 센키우놀라이드 H, 센키우놀라이드 I, 센키우놀라이드 J, 바닐린, 비타민 C로 이루어진 군으로부터 1종이상 선택된 화합물을 유효성분으로 포함하는 소화성 궤양 치료제를 제공한다.In addition, the present invention is adenosine, apiole, butylidenephthalide, butylphthalide, chlorogeninic acid, snidylide, coniperyl ferulate, ferulic acid, ligustilide, ligustildiol, neosnilide, pregne Nonol, Senkiunolide, Senkiunolide B, Senkiunolide C, Senkiunolide D, Senkiunolide F, Senkiunolide G, Senkiunolide H, Senkiunolide I, Sen Provided is a peptic ulcer therapeutic agent comprising at least one compound selected from the group consisting of quinolide J, vanillin and vitamin C as an active ingredient.
이하 본 발명을 상세하게 설명한다. Hereinafter, the present invention will be described in detail.
본 발명자들은 독성이 적고, 부작용이 없는 효과적인 소화성 궤양 치료제를 연구하던 중, 프로톤 펌프의 활성을 억제할 수 있는 화합물을 스크리닝하여 위산분비를 효과적으로 억제시킬 수 있는 유효 화합물들을 확인하였고, 이를 토대로 본 발명을 완성하였다.The inventors of the present invention, while studying an effective peptic ulcer treatment agent having low toxicity and no side effects, screened for compounds capable of inhibiting the activity of proton pumps and identified effective compounds capable of effectively inhibiting gastric acid secretion. Was completed.
본 발명의 유효 화합물은 하기 표 1로 나타낸 23종의 화합물들이다.The active compounds of the present invention are 23 compounds shown in Table 1 below.
(화학식 1) (화학식 2) (화학식 3) (화학식 4) (Formula 1) (Formula 2) (Formula 3) (Formula 4)
(화학식 5) (화학식 6) (화학식 7) (Formula 5) (Formula 6) (Formula 7)
(화학식 8) (화학식 9) (화학식 10) (화학식 11) (Formula 8) (Formula 9) (Formula 10) (Formula 11)
(화학식 12) (화학식 13) (화학식 14) (Formula 12) (Formula 13) (Formula 14)
(화학식 15) (화학식 16) (화학식 17) (화학식 18) (Formula 15) (Formula 16) (Formula 17) (Formula 18)
(화학식 19) (화학식 20) (화학식 21) (화학식 22) (Formula 19) (Formula 20) (Formula 21) (Formula 22)
(화학식 23) (Formula 23)
표 1에 기재한 화합물들은 H+/K+-ATPase 효소의 활성을 효과적으로 억제하는 것으로, 인 비트로 실험에서 관찰되었으며, 상기 화합물들 중 특히 아데노신, 아피올레, 부틸프탈라이드, 리구스틸라이드, 센키우놀라이드 및 바닐린은 95 % 이상의 높은 억제율을 나타내었다.The compounds listed in Table 1 have been observed in vitro to effectively inhibit the activity of the H + / K + -ATPase enzymes, and among these compounds, in particular adenosine, apiole, butylphthalide, ligustilide, and senkiu. Nolides and vanillins showed high inhibition rates of at least 95%.
이에, 본 발명에서는 아데노신, 아피올레, 부틸리덴네프탈라이드, 부틸프탈라이드, 클로로제닌산, 스니딜라이드, 코니페릴 페룰레이트, 페룰린산, 리구스틸라이드, 리구스틸리디올, 네오스니딜라이드, 프레그네노놀, 센키우놀라이드, 센키우놀라이드 B, 센키우놀라이드 C, 센키우놀라이드 D, 센키우놀라이드 F, 센키우놀라이드 G, 센키우놀라이드 H, 센키우놀라이드 I, 센키우놀라이드 J, 바닐린, 비타민 C 및 이들 각각의 유도체로 이루어진 군으로부터 1종이상 선택된 화합물을 유효성분으로 포함하는 위산분비 억제용 조성물을 제공한다. 상기 위산분비 억제용 조성물은 프로톤 펌프 억제기작을 이용한 것이다.Therefore, in the present invention, adenosine, apiole, butylidenephthalide, butylphthalide, chlorogeninic acid, snilide, coniferyl ferulate, ferulic acid, ligustilide, ligustilidiol, neosnilide, prepre Swingonol, Senkiunolide, Senkiunolide B, Senkiunolide C, Senkiunolide D, Senkiunolide F, Senkiunolide G, Senkiunolide H, Senkiunolide I, It provides a composition for inhibiting gastric acid secretion comprising at least one compound selected from the group consisting of senquiunolide J, vanillin, vitamin C and their respective derivatives as an active ingredient. The composition for inhibiting gastric acid secretion is to use a proton pump suppression mechanism.
본 발명의 위산분비 억제용 조성물은 상기 화합물 각각을 단독 또는 2종 이상으로 포함할 수 있으며, 그 외 약리학적으로 허용 가능한 담체를 더욱 포함할 수 있다. 상기 담체로는 대표적으로 물, 덱스트린, 생리식염수, 폴리에틸 글리세롤 및 카복실 메틸 셀룰로즈가 있다. 위산분비 억제용 조성물에 포함되는 화합물의 함량은 0.001 내지 70 중량%일 수 있다. 상기 화합물의 함량이 조성물에 0.001 중량% 미만으로 포함되는 경우 그 효능이 상실될 수 있으며, 70 중량% 초과하는 경우 효율대비 비경제적일 수 있다. The composition for inhibiting gastric acid secretion of the present invention may include each of the above compounds alone or two or more, and may further include a pharmacologically acceptable carrier. Such carriers are typically water, dextrin, physiological saline, polyethyl glycerol and carboxyl methyl cellulose. The content of the compound included in the composition for inhibiting gastric acid secretion may be 0.001 to 70% by weight. When the amount of the compound is included in the composition in less than 0.001% by weight may be lost its efficacy, when it exceeds 70% by weight may be uneconomical efficiency.
본 발명의 위산분비 억제용 조성물은 경구 또는 비경구로 사용할 수 있으며, 바람직하기로는 경구투여이다. 위산분비 억제용 조성물은 식품, 식품첨가제 또는 약제로 사용가능하다. 약제로 사용하는 경우 약제학적 분야에서 공지의 방법에 의하여 제조할 수 있으며, 그 형태로는 산제(POWDERS), 과립제(GRANULES), 정제(TABLETS), 유동 엑스제(FLUIDEXTRACTS), 유제 및 현탁제(EMULSIONS AND SUSPESIONS), 캅셀제(CAPSULES), 환제(PILLS), 트로키제(troche), 액제(LIQUIDS AND SOLUTIONS) 및 시럽제(SYRUPS) 일 수 있다. 식품 또는 식품첨가제로 사용하는 경우 음료나 건강식품으로 활용가능하다. Gastric acid secretion inhibiting composition of the present invention can be used orally or parenterally, preferably oral administration. Gastric acid secretion inhibiting composition can be used as food, food additives or drugs. When used as a pharmaceutical can be prepared by a method known in the pharmaceutical field, in the form of powder (POWDERS), granules (GRANULES), tablets (TABLETS), fluid extracts (FLUIDEXTRACTS), emulsions and suspensions ( EMULSIONS AND SUSPESIONS, CAPSULES, PILLS, TROCHES, LIQUIDS AND SOLUTIONS, and SYRUPS. When used as a food or food additive, it can be used as a beverage or health food.
본 발명의 위산분비 억제용 조성물은 사용용도 및 환자상태에 따라 조절하여 사용하는 것이 바람직하며, 1 회 투여시 성인 체중 1 ㎏을 기준으로 상기 표 1의 화합물을 0.001 내지 500 ㎎의 용량으로 사용할 수 있다. Composition for inhibiting gastric acid secretion of the present invention is preferably used according to the use and patient condition, the compound of Table 1 can be used in a dose of 0.001 to 500 mg based on 1 kg of adult body weight per dose have.
또한 본 발명의 위산분비 억제용 조성물은 소화성 궤양 치료제로 사용할 수 있다.In addition, the composition for inhibiting gastric acid secretion of the present invention can be used as a therapeutic agent for peptic ulcer.
이하 본 발명의 바람직한 실시예 및 비교예를 기재한다. 그러나, 하기한 실시예는 본 발명의 바람직한 일 실시예일 뿐 본 발명이 하기한 실시예에 한정되는 것은 아니다. Hereinafter, preferred examples and comparative examples of the present invention are described. However, the following examples are only preferred embodiments of the present invention and the present invention is not limited to the following examples.
(실시예) HExample H ++ /K/ K ++ -ATPase 효소에 대한 위산 분비 억제효과 -Inhibition of gastric acid secretion on -ATPase enzyme
상기 표 1로 기재한 총 23종의 화합물을 제조사(sigma, merk, difco 등)로부터 구입하고, 각각의 화합물에 대하여 인 비트로(in vitro) 위산 분비 억제효과를 측정하였다.A total of 23 compounds listed in Table 1 were purchased from manufacturers (sigma, merk, difco, etc.), and the in vitro gastric acid secretion inhibitory effect was measured for each compound.
위산을 분비하는 효소인 H+/K+-ATPase를 뉴질랜드산 흰토끼의 위조직으로부터 분리하고, 분리한 효소에 각각의 화합물을 200 ㎍/㎖로 DMSO(dimethyl sulfoxide) 용액에 녹여 제조한 혼합용액을 첨가하였다. 37 ℃에서 30 분 동안 인큐베이션하고, H+/K+-ATPase 효소의 활성 억제율을 하기 계산식 1에 따라 환산하였다. 또한, 대조군으로 DMSO 용액을 단독으로 처리하여 H+/K+-ATPase 효소의 활성 억제율을 측정하였다.A solution prepared by separating H + / K + -ATPase, a gastric acid secreting enzyme from the gastric tissue of New Zealand white rabbit, and dissolving each compound in DMSO (dimethyl sulfoxide) solution at 200 ㎍ / ml Was added. Incubated at 37 ° C. for 30 minutes, and the activity inhibition rate of H + / K + -ATPase enzyme was converted according to the following formula (1). In addition, DMSO solution alone was treated as a control to measure the inhibition rate of H + / K + -ATPase enzyme activity.
상기 화합물 각각의 H+/K+-ATPase 효소의 활성 억제율을 하기 계산식 1에 따라 계산하여 위산 분비 억제 효과를 측정하고, 그 결과는 하기 표 2에 나타내었다.The inhibition rate of H + / K + -ATPase enzyme activity of each compound was calculated according to Formula 1 below to determine the effect of inhibiting gastric acid secretion, and the results are shown in Table 2 below.
(계산식 1)(Calculation 1)
표 2에서, 화합물 모두는 H+/K+-ATPase 효소 활성을 억제하였으며, 특히 아데노신, 아피올레, 부틸프탈라이드, 리구스틸라이드, 센키우놀라이드 및 바닐린의 H+/K+-ATPase 효소 활성 억제율이 95 % 이상으로 가장 우수하였다.In Table 2, the compounds are all H + / K + -ATPase activity was suppressed, in particular adenosine, Bahia oleic, butylphthalide, Liguria steel fluoride, metallocene grow surprisingly Id and H + / K + -ATPase activity of vanillin The inhibition was the best with 95% or more.
이상 살펴본 바와 같이, 본 발명의 23종의 화합물은 프로톤 펌프를 효과적으로 억제할 수 있어, 이를 위산 분비 억제제 및 소화성 궤양 치료제로 사용할 수 있다.As described above, 23 compounds of the present invention can effectively inhibit the proton pump, it can be used as a gastric acid secretion inhibitor and peptic ulcer therapeutic agent.
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JP2013063957A (en) * | 2011-09-02 | 2013-04-11 | Kao Corp | Glp-1 secretion promoter |
JP2014515361A (en) * | 2011-05-20 | 2014-06-30 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | CB1 receptor antagonist |
US10259839B2 (en) | 2012-11-28 | 2019-04-16 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | 3-(4′-substituted)-benzyl-ether derivatives of pregnenolone |
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JP2014515361A (en) * | 2011-05-20 | 2014-06-30 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | CB1 receptor antagonist |
JP2016104772A (en) * | 2011-05-20 | 2016-06-09 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | Antagonists of cb1 receptor |
US10040816B2 (en) | 2011-05-20 | 2018-08-07 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Antagonists of CB1 receptor |
US10150793B2 (en) | 2011-05-20 | 2018-12-11 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Antagonists of CB1 receptor |
JP2013063957A (en) * | 2011-09-02 | 2013-04-11 | Kao Corp | Glp-1 secretion promoter |
CN102716160A (en) * | 2012-06-28 | 2012-10-10 | 天津大学 | Hemlock parsley phthalide type ingredient effective part as well as preparation method and application of hemlock parsley phthalide type ingredient effective part |
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