WO2007105286A1 - Blood lipid level-lowering agent - Google Patents

Blood lipid level-lowering agent Download PDF

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Publication number
WO2007105286A1
WO2007105286A1 PCT/JP2006/304862 JP2006304862W WO2007105286A1 WO 2007105286 A1 WO2007105286 A1 WO 2007105286A1 JP 2006304862 W JP2006304862 W JP 2006304862W WO 2007105286 A1 WO2007105286 A1 WO 2007105286A1
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lowering agent
blood
blood lipid
compound
cholesterol
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PCT/JP2006/304862
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French (fr)
Japanese (ja)
Inventor
Kazuhiro Anabuki
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Agro Kanesho Co., Ltd.
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Priority to PCT/JP2006/304862 priority Critical patent/WO2007105286A1/en
Publication of WO2007105286A1 publication Critical patent/WO2007105286A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/02—Halogenated hydrocarbons
    • A61K31/035—Halogenated hydrocarbons having aliphatic unsaturation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Definitions

  • the present invention relates to a blood lipid lowering agent containing perchloro 1,1′-bicyclocyclopenter 2,4 gen, particularly a blood cholesterol lowering agent.
  • Perchloro 1,1'-bicyclocyclopenter 2, 4 gen (hereinafter also referred to simply as "the present compound") is a known compound and is called dienochlor. Known as.
  • this compound has a function of lowering blood lipids, particularly blood cholesterol.
  • the present invention provides a blood lipid lowering agent that lowers cholesterol and phospholipid among lipids in blood (particularly cholesterol, neutral lipid and phospholipid) without causing serious side effects.
  • the purpose is to provide.
  • This compound has a function of lowering blood cholesterol particularly in patients with hypercholesterolemia and high cholesterol concentration in blood, and is an excellent blood cholesterol lowering agent.
  • the present inventors have studied the action of the above-mentioned perchloro 1,1'-bicyclocyclopentater 2, 4 gen known as an acaricide, and surprisingly, the present compound is found in animals. It has been found that it has an action of lowering lipids in blood, particularly blood cholesterol. The present inventor has completed the present invention based on this new knowledge.
  • the present invention relates to a blood lipid lowering agent containing perchloro 1,1′-bicyclocyclopenter 2,4 gen as an active ingredient, particularly a blood cholesterol lowering agent (hereinafter referred to as “blood lipid lowering”).
  • a blood lipid lowering agent containing perchloro 1,1′-bicyclocyclopenter 2,4 gen as an active ingredient, particularly a blood cholesterol lowering agent (hereinafter referred to as “blood lipid lowering”).
  • blood lipid lowering a blood cholesterol lowering agent
  • the blood lipid lowering agent of the present invention has an excellent effect of lowering blood lipid in mammals. Therefore, the present invention is excellent in the treatment of hyperlipidemia and is useful for the treatment and prevention of myocardial infarction, cerebral infarction, peripheral artery occlusion, arteriosclerosis and the like caused by hyperlipidemia.
  • perchloro 1,1′-bicyclocyclopenter 2,4 gen is a known compound, and is described in, for example, US Pat. No. 2,908,723 and US Pat. No. 2,934,470. .
  • This compound is, for example, the following reductive dimerization with hydrogen in the presence of a catalyst of the following compound II (hexachlorocyclopentagen), which is readily available in the field. Therefore, it can be easily prepared.
  • examples of the catalyst include noble metals of group VIII of the periodic table, such as
  • the present compound can be easily obtained in the factory as dienochlor. Further, the purification method is obvious to those skilled in the art. For example, dienochlor can be obtained in high purity by purifying it by recrystallization or column chromatography.
  • test substance was filled into gelatin capsules at a weight of 8, 40 and 200 mgZKg body weight and administered orally once daily to 4 male and 4 female beagle dogs.
  • empty gelatin capsules were administered as in the test animals.
  • the cholesterol value was calculated by an enzymatic method.
  • Phospholipids were calculated by an enzymatic method.
  • A1 is an average cholesterol value or phospholipid value in the control group
  • A2 is a corresponding value after elapse of a predetermined period.
  • the rate of cholesterol reduction is as shown in Table 1 below.
  • the amount of blood cholesterol in the control group was 155 to 192 mgZdl.
  • the amount of blood phospholipid in the control group was 324 to 377 mg Zdl.
  • the blood concentration of cholesterol and phospholipids greatly decreases depending on the dose in the number of days after administration.
  • the dose exceeds 3 days at 3 mg / K, the reduction effect is prominent. This effect is also seen in female test animals. It can also be seen that it is not particularly affected by males.
  • this compound acts as a blood lipid lowering agent or blood cholesterol lowering agent on mammals including humans as they are or mixed with excipients.
  • This compound can be administered in the form of tablets, granules, powders, injections, percutaneous absorptions, etc., which are not limited to capsules, either as oral or parenteral dosage forms. it can.
  • the dose of this compound can be appropriately varied depending on the degree of symptoms, age, weight, dosage form and the like. In general, it is 0.1 to 1000 mg / Kg body weight / day, preferably 2 to 500 mg / Kg body weight / day, particularly preferably 3 to 250 mg / Kg body weight / day per day.
  • the administration can be performed once or divided into several times.
  • any additive can be used depending on the dosage form.
  • excipients include lactose, excipients such as mannitol, crystalline cellulose, and dampener, lubricants such as magnesium stearate and talc, hydroxypropylcellulose calcium, low-substituted hydroxypropyl, and the like.
  • a disintegrating agent such as methylcellulose, a coating agent such as hydroxypropylmethylcellulose, macrogol, Eudragit, and silicone resin can be appropriately blended as necessary.
  • Capsule shell (gelatin capsule)
  • the present invention provides an excellent blood lipid lowering agent or blood cholesterol lowering agent that does not cause serious side effects.

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  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
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Abstract

It is intended to provide a blood lipid level-lowering agent or a blood cholesterol level-lowering agent having an excellent effect without showing any severe side effects. These agents contain, as the active ingredient, perchloro-1,1’-bicyclopenta-2,4-diene.

Description

血中脂質低下剤  Blood lipid lowering agent
技術分野  Technical field
[0001] 本発明は、パークロロ 1, 1'ービシクロシクロペンター 2, 4 ジェンを含有する血 中脂質低下剤、特に、血中コレステロール低下剤に関する。  The present invention relates to a blood lipid lowering agent containing perchloro 1,1′-bicyclocyclopenter 2,4 gen, particularly a blood cholesterol lowering agent.
背景技術  Background art
[0002] 次式、 [0002]
[0003] [化 1] [0003] [Chemical 1]
Figure imgf000002_0001
で示されるパークロロ 1, 1'ービシクロシクロペンター 2, 4 ジェン（以下、単に「本 化合物」ともいう）は、公知化合物であり、ジエノクロール（Dienochlor)と呼ばれ、これ まで、ダニの防御剤として知られている。
Figure imgf000002_0001
Perchloro 1,1'-bicyclocyclopenter 2, 4 gen (hereinafter also referred to simply as "the present compound") is a known compound and is called dienochlor. Known as.
し力しながら、本化合物が、血中脂質、特に、血中コレステロールを低下させる機能 を有することは、全く知られていなカゝつた。  However, it has never been known that this compound has a function of lowering blood lipids, particularly blood cholesterol.
発明の開示  Disclosure of the invention
発明が解決しょうとする課題  Problems to be solved by the invention
[0004] 本発明は、重篤な副作用を生じることなぐ血中における脂質 (特に、コレステロ一 ル、中性脂質及びリン脂質)の内、コレステロール及びリン脂質を低下させる血中脂 質低下剤を提供することを目的とする。本化合物は、特に、高コレステロール血症や 、血中におけるコレステロール濃度の高い患者における血中コレステロールを低下さ せる機能を有し、優れた血中コレステロール低下剤となる。 [0004] The present invention provides a blood lipid lowering agent that lowers cholesterol and phospholipid among lipids in blood (particularly cholesterol, neutral lipid and phospholipid) without causing serious side effects. The purpose is to provide. This compound has a function of lowering blood cholesterol particularly in patients with hypercholesterolemia and high cholesterol concentration in blood, and is an excellent blood cholesterol lowering agent.
課題を解決するための手段 [0005] 本発明者らは、殺ダニ剤として公知の上記パークロロ 1, 1'ービシクロシクロペン ター 2, 4 ジェンの作用について検討していたところ、驚くべきことに、本化合物が、 動物における血中における脂質、特に血中コレステロールを低下させる作用を有す ることを見出した。本発明者は、この新たな知見に基づき、本発明を完成したもので ある。 Means for solving the problem [0005] The present inventors have studied the action of the above-mentioned perchloro 1,1'-bicyclocyclopentater 2, 4 gen known as an acaricide, and surprisingly, the present compound is found in animals. It has been found that it has an action of lowering lipids in blood, particularly blood cholesterol. The present inventor has completed the present invention based on this new knowledge.
即ち、本発明は、パークロロ 1, 1'ービシクロシクロペンター 2, 4 ジェンを有効 成分として含有する血中脂質低下剤、特に、血中コレステロール低下剤（以下、合わ せて「血中脂質低下剤」と言う）に関するものである。  That is, the present invention relates to a blood lipid lowering agent containing perchloro 1,1′-bicyclocyclopenter 2,4 gen as an active ingredient, particularly a blood cholesterol lowering agent (hereinafter referred to as “blood lipid lowering”). Agent ").
発明の効果  The invention's effect
[0006] 本発明の血中脂質低下剤は、哺乳動物において、優れた血中脂質を低下させる 作用を有する。そのため、本発明は、高脂血症の治療に優れるとともに、高脂血症に 起因する心筋梗塞や、脳梗塞、抹消動脈閉塞、動脈硬化症等の治療、予防に有用 である。  [0006] The blood lipid lowering agent of the present invention has an excellent effect of lowering blood lipid in mammals. Therefore, the present invention is excellent in the treatment of hyperlipidemia and is useful for the treatment and prevention of myocardial infarction, cerebral infarction, peripheral artery occlusion, arteriosclerosis and the like caused by hyperlipidemia.
発明を実施するための最良の形態  BEST MODE FOR CARRYING OUT THE INVENTION
[0007] 以下、本発明ついて、更に詳細に説明する。 [0007] Hereinafter, the present invention will be described in more detail.
本発明で使用される次式、  The following formula used in the present invention:
Figure imgf000003_0001
Figure imgf000003_0001
[0008] で示されるパークロロ 1, 1'ービシクロシクロペンター 2, 4 ジェンは、公知化合物 であり、例えば、米国特許第 2908723号明細書や、米国特許第 2934470号明細 書に記載されている。 [0008] perchloro 1,1′-bicyclocyclopenter 2,4 gen is a known compound, and is described in, for example, US Pat. No. 2,908,723 and US Pat. No. 2,934,470. .
本化合物は、例えば、巿場において容易に入手可能な以下の化合物 II (へキサクロ ロシクロペンタジェン）を、触媒の存在下において、水素で還元的に 2量化することに よって、容易に調製することができる。 This compound is, for example, the following reductive dimerization with hydrogen in the presence of a catalyst of the following compound II (hexachlorocyclopentagen), which is readily available in the field. Therefore, it can be easily prepared.
[化 3]  [Chemical 3]
Figure imgf000004_0001
Figure imgf000004_0001
[0009] 上記製造方法において、触媒としては、例えば、周期律表 VIII族の貴金属、例えば [0009] In the above production method, examples of the catalyst include noble metals of group VIII of the periodic table, such as
、ルテニウムや、ノ《ラジウム、オスミウム、ラジウム、白金、銅等の金属又はその化合物 が使用される。具体的な調製方法は、例えば、上記米国特許に記載されている。 なお、本化合物は、上記の通り、ジエノクロールとして巿場において容易に入手可 能である。また、その精製法は、当業者には、 自明である。例えば、ジエノクロールは 、再結晶化法や、カラムクロマトグラフィー法で精製することによって、本化合物を高 純度で得ることができる。 , Ruthenium, metal << radium, osmium, radium, platinum, copper, or a compound thereof. Specific preparation methods are described, for example, in the above US patents. As described above, the present compound can be easily obtained in the factory as dienochlor. Further, the purification method is obvious to those skilled in the art. For example, dienochlor can be obtained in high purity by purifying it by recrystallization or column chromatography.
[ooio] (血中脂質の低下効果の確認）  [ooio] (Confirmation of blood lipid lowering effect)
被枪物皙  Stuff
ジエノクロール（純度 99. 5%)  Dienochlor (purity 99.5%)
碰誦  碰 誦
投与開始時、 6力月令のビーグル犬  6-month-old beagle at the start of administration
1群雌雄各 4例（投与開始時体重 雄 8. 1〜9. 5Kg、雌 7. 2〜8. 6Kg) 訧験 去  1 group, 4 males and 4 females (body weight at start of administration: 8.1 to 9.5 kg, female to 7.2 to 8.6 kg)
1群雌雄各 4例のビーグル犬に、 8、 40及び 200mgZKg体重で、被検物質をゼラ チンカプセルに充填して、毎日 1回経口投与した。対照群には、空のゼラチンカプセ ルを、試験動物の場合と同様に投与した。  The test substance was filled into gelatin capsules at a weight of 8, 40 and 200 mgZKg body weight and administered orally once daily to 4 male and 4 female beagle dogs. In the control group, empty gelatin capsules were administered as in the test animals.
[0011] コレステロール値及びリン脂皙値の測定方法 [0011] Method for measuring cholesterol level and phospholipid level
コレステロール値は、酵素法によって算出した。  The cholesterol value was calculated by an enzymatic method.
リン脂質は、酵素法によって算出した。  Phospholipids were calculated by an enzymatic method.
[0012] コレステロール値及びリン脂皙値の低減率の寛出方法 次式 (I)のより求めた。 [0012] A method for eradicate the reduction rate of cholesterol level and phospholipid level It was obtained from the following formula (I).
(1 -A2/A1) X 100 (%) (I)  (1 -A2 / A1) X 100 (%) (I)
[0013] 式中、 A1は、対照群における平均コレステロール値又はリン脂質値であり、 A2は、 所定期間経過後の対応する値である。 [0013] In the formula, A1 is an average cholesterol value or phospholipid value in the control group, and A2 is a corresponding value after elapse of a predetermined period.
[0014] 腿 [0014] thigh
コレステロールの低下率は、以下の表 1に記載の通りである。  The rate of cholesterol reduction is as shown in Table 1 below.
表 1  table 1
Figure imgf000005_0001
なお、対照群の血中コレステロールの量は、 155〜192 mgZdlであった。
Figure imgf000005_0001
The amount of blood cholesterol in the control group was 155 to 192 mgZdl.
[0015] リン脂質の低下率は、以下の表 2に記載の通りである。 [0015] The reduction rate of phospholipid is as shown in Table 2 below.
表 2  Table 2
Figure imgf000005_0002
なお、対照群の血中リン脂質の量は、 324〜377mgZdlであった。
Figure imgf000005_0002
The amount of blood phospholipid in the control group was 324 to 377 mg Zdl.
[0016] 上記表 1及び 2より分力るように、投与からの経時日数にお!、て、投与量に応じて、 コレステロール及びリン脂質の血中濃度が大きく低下する。特に、投与量が、 3mg/K も I日を超えると、その低下効果が顕著に見られる。また、この効果は、試験動物の雌 雄によって実際上特に影響を受けな 、ことも分かる。 [0016] As shown in the above Tables 1 and 2, the blood concentration of cholesterol and phospholipids greatly decreases depending on the dose in the number of days after administration. In particular, when the dose exceeds 3 days at 3 mg / K, the reduction effect is prominent. This effect is also seen in female test animals. It can also be seen that it is not particularly affected by males.
なお、投与試験において、特に重大な副作用や、症状は観察されな力 た。例え ば、投与試験期間中、尿素窒素や、血糖値は、実際上安定していた。従って、ビー ダル犬としての日常の行動や動きに対して、特に大きな影響は見られな力つた。  In the administration study, no serious side effects or symptoms were observed. For example, urea nitrogen and blood glucose levels were practically stable during the administration test period. Therefore, it did not have a significant effect on daily activities and movements as a beal dog.
[0017] 毒性について  [0017] Toxicity
本化合物は、 300mg/Kg体重の割合でビーグル犬に経口投与しても、死亡例は認 められな力つた。従って、本化合物は、そのまま、又は賦形剤等とともに混合してヒト を含む哺乳動物類に対して、血中脂質低下剤若しくは血中コレステロール低下剤と して作用する。  Even when this compound was orally administered to beagle dogs at a rate of 300 mg / Kg body weight, no deaths were observed. Therefore, this compound acts as a blood lipid lowering agent or blood cholesterol lowering agent on mammals including humans as they are or mixed with excipients.
[0018] 本化合物の投与は、経口、非経口のどちらでもよぐ剤形としても、カプセルだけで はなぐ錠剤や、顆粒剤、散剤、注射剤、経皮吸収剤等の形態で行うことができる。 本化合物の投与量は、症状の程度や、年齢、体重、剤形等によって適宜変動させる ことができる。一般に、 1日当たり、 0.1〜1000mg/Kg体重、好ましくは、 2〜500mg/Kg 体重/日、特に好ましくは、 3〜250mg/Kg体重/日である。  [0018] This compound can be administered in the form of tablets, granules, powders, injections, percutaneous absorptions, etc., which are not limited to capsules, either as oral or parenteral dosage forms. it can. The dose of this compound can be appropriately varied depending on the degree of symptoms, age, weight, dosage form and the like. In general, it is 0.1 to 1000 mg / Kg body weight / day, preferably 2 to 500 mg / Kg body weight / day, particularly preferably 3 to 250 mg / Kg body weight / day per day.
投与は、 1回又は数回に分けて行うことができる。  The administration can be performed once or divided into several times.
[0019] 本ィ匕合物の製剤化に当たっては、剤形に応じて、任意の添加剤を使用することが できる。このような賦形剤としては、例えば、乳糖や、マンニット、結晶セルロース、デ ンプン等の賦形剤や、ステアリン酸マグネシウム、タルク等の滑沢剤、ヒドロキシプロ ピルセルロースカルシウム、低置換ヒドロキシプロピルメチルセルロース等の崩壊剤、 ヒドロキシプロピルメチルセルロース、マクロゴール、オイドラギット、シリコン榭脂等の コーティング剤などを必要に応じて適宜配合することができる。  [0019] In formulating the present compound, any additive can be used depending on the dosage form. Examples of such excipients include lactose, excipients such as mannitol, crystalline cellulose, and dampener, lubricants such as magnesium stearate and talc, hydroxypropylcellulose calcium, low-substituted hydroxypropyl, and the like. A disintegrating agent such as methylcellulose, a coating agent such as hydroxypropylmethylcellulose, macrogol, Eudragit, and silicone resin can be appropriately blended as necessary.
[0020] 以下において、本発明の処方例を示す。 [0020] In the following, formulation examples of the present invention are shown.
処方例 1 (カプセル剤） (150mg)  Formulation Example 1 (Capsule) (150mg)
(1)カプセル殻部分 (ゼラチンカプセル）  (1) Capsule shell (gelatin capsule)
(2)内包成分  (2) Inclusion component
本ィ匕合物 5mg  This compound 5mg
乳糖 145mg  Lactose 145mg
[0021] 処方例 2 (錠剤) 本化合物 lOOmg [0021] Formulation Example 2 (tablet) This compound lOOmg
乳糖 50mg Lactose 50mg
トウモロコシでんぷん 15mg Corn starch 15mg
力ノレボキシノレメチノレセノレロースカノレシゥム 44mg Force Nolevoxino Remethino Resenorelose Canolecium 44mg
ステアリン酸マグネシウム lmg Magnesium stearate lmg
処方例 3 (顆粒剤) Formulation Example 3 (Granule)
(処方 lOOmg中） (In prescription lOOmg)
本化合物 30mg This compound 30mg
マン-ッ卜 47mg Mantsu 47mg
ポリビニノレピロリドン K— 30 7mg Polyvinylenopyrrolidone K— 30 7mg
オイドラギット RL 15mg Eudragit RL 15mg
トリァセチン 2mg Triacetin 2mg
以上の通り、本発明は、重篤な副作用を生じることない、優れた血中脂質低下剤若 しくは、血中コレステロール低下剤が提供される。  As described above, the present invention provides an excellent blood lipid lowering agent or blood cholesterol lowering agent that does not cause serious side effects.

Claims

Figure imgf000008_0001
Figure imgf000008_0001
ビシクロシクロペンター 2, 4 ジェンを有効成分とし  Bicyclocyclopenter 2, 4 Gen as active ingredient
Figure imgf000008_0002
Figure imgf000008_0002
で示されるパークロロ 1, 1，ービシクロシクロペンター 2, 4 ジェンを有効成分とし て含有する血中コレステロール低下剤。  A blood cholesterol lowering agent containing perchloro 1,1, -bicyclocyclopenta 2, 4 gen as shown in FIG.
高コレステロール血症を治療する医薬の製造における、次式、  In the manufacture of a medicament for treating hypercholesterolemia,
[化 3]  [Chemical 3]
Figure imgf000008_0003
で示されるパークロロ 1, 1，ービシクロシクロペンター 2, 4 ジェンの使用
Figure imgf000008_0003
Use of perchloro 1,1, -bicyclocyclopenter 2, 4 gen represented by
PCT/JP2006/304862 2006-03-13 2006-03-13 Blood lipid level-lowering agent WO2007105286A1 (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2934470A (en) * 1955-06-27 1960-04-26 Hooker Chemical Corp Insecticidal perchlorocarbon
JP2006083074A (en) * 2004-09-14 2006-03-30 Agro Kanesho Co Ltd Blood lipid lowering agent

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2934470A (en) * 1955-06-27 1960-04-26 Hooker Chemical Corp Insecticidal perchlorocarbon
JP2006083074A (en) * 2004-09-14 2006-03-30 Agro Kanesho Co Ltd Blood lipid lowering agent

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ISHIKAWA T. ET AL.: "Effects of Chlorinated Hydrocarbons on Plasma alpha-Lipoprotein Cholesterol in Rats", METABOLISM, vol. 27, no. 1, 1978, pages 89 - 96, XP026300647, DOI: doi:10.1016/0026-0495(78)90127-0 *
MADHUKAR B.V. ET AL.: "Comparison of Induction Patterns of Rat Hepatic Microsomal Mixed-Function Oxidases by Pesticides and Related Chemicals", PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, vol. 11, no. 1-3, 1979, pages 301 - 308, XP024867135, DOI: doi:10.1016/0048-3575(79)90070-1 *

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