JPH0474131A - Production of phospholipid-analog compound free from nitrogen and having hypotensive action - Google Patents
Production of phospholipid-analog compound free from nitrogen and having hypotensive actionInfo
- Publication number
- JPH0474131A JPH0474131A JP2185246A JP18524690A JPH0474131A JP H0474131 A JPH0474131 A JP H0474131A JP 2185246 A JP2185246 A JP 2185246A JP 18524690 A JP18524690 A JP 18524690A JP H0474131 A JPH0474131 A JP H0474131A
- Authority
- JP
- Japan
- Prior art keywords
- phospholipid
- nitrogen
- analog compound
- blood pressure
- free
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 title claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 230000001077 hypotensive effect Effects 0.000 title abstract 2
- 240000001080 Grifola frondosa Species 0.000 claims abstract description 13
- 235000007710 Grifola frondosa Nutrition 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 230000004531 blood pressure lowering effect Effects 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 7
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
- 206010020772 Hypertension Diseases 0.000 abstract description 4
- 238000002347 injection Methods 0.000 abstract description 3
- 239000007924 injection Substances 0.000 abstract description 3
- 238000004811 liquid chromatography Methods 0.000 abstract description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 abstract description 2
- 235000012239 silicon dioxide Nutrition 0.000 abstract description 2
- 235000013399 edible fruits Nutrition 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 15
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 12
- 239000010410 layer Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000005923 long-lasting effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 102000014384 Type C Phospholipases Human genes 0.000 description 2
- 108010079194 Type C Phospholipases Proteins 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000957 no side effect Toxicity 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000003283 Pachira macrocarpa Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 240000001085 Trapa natans Species 0.000 description 1
- 235000014364 Trapa natans Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000009165 saligot Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は本願発明者等が特開昭６２〜１９５３３４号で
開示した技術内容をより研鏝を加え開発した高血圧症に
用いる非窒素含有燐脂質血圧値降下化合物に関するもの
である。Detailed Description of the Invention [Industrial Application Field] The present invention relates to a non-nitrogen-containing phosphorus for use in hypertension, which was developed by the inventors of the present invention by further researching the technical contents disclosed in JP-A-62-195334. This invention relates to lipid blood pressure lowering compounds.
［従来技術の問題点］
近年血圧降下作用を促す各種の物質の開発、その進展は
著しく本件に係る化合物は数多（発明され開示されてい
る。[Problems with the Prior Art] In recent years, the development of various substances that promote blood pressure lowering effects has made remarkable progress, and a large number of compounds related to the present invention have been invented and disclosed.
しかしながら上記、−船釣にこれらの作用を示す物質分
子内には窒素化合物が含まれている。However, the molecules of the substances that exhibit these effects in boat fishing contain nitrogen compounds.
しかしこれらの物質はその持続性や即効性等に難点をも
つものが少なくない。However, many of these substances have drawbacks such as their sustainability and immediate effect.
そこで長時間に亘っての持続性を有し、かつ即効性を有
する物質の開発が要望されている。Therefore, there is a demand for the development of a substance that has a long-lasting effect and has an immediate effect.
本発明に用いられるキノコ類、特にマイタケは従来より
栗、みずなら、等の古木に自生する天然のキノコであり
、漢方薬の配合原料として、従来より珍重されてきた。Mushrooms used in the present invention, particularly maitake, are naturally occurring mushrooms that grow naturally on old trees such as chestnuts and water chestnuts, and have traditionally been prized as ingredients for herbal medicine.
近年、該マイタケ自体に含有されている各種の成分を抽
出しこれを制癌作用を有する薬剤や、又健康食品・・・
等に利用し、注目されているキノコである。In recent years, various components contained in the maitake mushroom itself have been extracted and used as drugs with anticancer effects, health foods, etc.
It is a mushroom that is attracting attention as it is used for various purposes.
近時、該マイタケの人工栽培による生産法が開発され多
量の需要に対応できることが可能となった。Recently, a production method using artificial cultivation of maitake mushrooms has been developed, and it has become possible to meet the large demand.
［発明の目的］
本発明は、上記の事由に鑑みて、キノコ類特にマイタケ
科に属するキノコを原材料として血圧降下作用を有する
薬物を抽出し臨床医学的に経口投専決のみならず、注射
法においても即効性を有し、かつ長時間の持続性並びに
副作用を皆無と成した物質を発明することを目的とする
ものである。[Purpose of the Invention] In view of the above reasons, the present invention has been made to extract a drug having a blood pressure lowering effect from mushrooms, particularly mushrooms belonging to the Maitake family, and to provide a drug that can be administered clinically not only orally but also by injection. The purpose of the present invention is to invent a substance that has an immediate effect, is long-lasting, and has no side effects.
［発明の概要コ
本発明の、キノコはサルノコシカケ科に属するマイタケ
（シロマイタケ、トンビマイタケ）を原材料とし、該マ
イタケ菌糸体及び子実体より血圧降下作用を有する物質
を抽出できることは、上述の如く本件発明者等が特開昭
６２〜１９５３３４号公報で開示した様に明らかである
が本発明においては、同一原材料より血圧降下作用を有
する新規物質を抽出し、該物質の化学構造を明示するも
のである。[Summary of the Invention] The mushroom of the present invention is made from maitake (Shiromaitake, Tombimaitake), which belongs to the family Arunococcinaceae, and the substance having a blood pressure lowering effect can be extracted from the maitake mycelium and fruiting body, as described above. As disclosed by the inventors in JP-A-62-195334, it is clear that in the present invention, a new substance having a blood pressure lowering effect is extracted from the same raw material and the chemical structure of the substance is specified. be.
以下、本発明の新規化合物質の抽出方法を具体的に説明
する。Hereinafter, the method for extracting the novel chemical compound of the present invention will be specifically explained.
化マイタケ又は、乾燥マイタケ、或いは粉末マイタケを
エーテルと混合させ５０℃で約３時間熱処理の後、得ら
れた抽出物を更に濃縮する。Maitake mushrooms, dried Maitake mushrooms, or powdered Maitake mushrooms are mixed with ether and heated at 50° C. for about 3 hours, and the resulting extract is further concentrated.
次に、アセトンで処理し、アセトン可溶物（ＥＳ−ＡＳ
）とアセトン不溶物（ＥＳ−ＡＰ）に分離する。Next, it was treated with acetone, and the acetone soluble material (ES-AS
) and acetone insoluble matter (ES-AP).
ＥＳ−ＡＳ−ＥＳ−ＡＰ共に血圧降下作用を示すが、後
者のＥＳ−ＡＰ物質を更にケイ酸を充填したかラムに吸
着させ、クロロホルム−メタノール水（１３０，５０：
８）の混合液を用いて溶出させ、５画分を取得する。Both ES-AS-ES-AP exhibit a blood pressure lowering effect, but the latter ES-AP substance was further filled with silicic acid or adsorbed in a ram, and chloroform-methanol water (130, 50:
Elute using the mixture of step 8) to obtain 5 fractions.
これらの画分は何れも血圧降下作用を示すが、この内特
に、該血圧降下作用が強（認められる画分を、コスモシ
ール５Ｃ１８カラムを担体とする液体クロマトグラフ法
で精製し、得られた物質を、ＥＳ−ＡＰ−３と命名する
。All of these fractions exhibit a blood pressure lowering effect, but among these, the blood pressure lowering effect is particularly strong (the fractions found were purified by liquid chromatography using a Cosmo Seal 5C18 column as a carrier). The material is named ES-AP-3.
なお、該物質の溶出には、ニーテール−メタノールの混
合液を用いる。Note that a mixture of Nytail and methanol is used to elute the substance.
次に上記、ＥＳ−ＡＰ−３の、脱アシル化処理を行う。Next, the above-described deacylation treatment of ES-AP-3 is performed.
即ち、クロロホルム−メタノール混合液中にメタノール
性苛性ソーダを添加し、一定時間２７℃で放置後、更に
クロロホルム−メタノール−水の混合液を加え混和する
。That is, methanolic caustic soda is added to a chloroform-methanol mixture, and after the mixture is left at 27° C. for a certain period of time, a chloroform-methanol-water mixture is further added and mixed.
続いて、遠心分離機でメタノール−水の層とクロロホル
ム層とに分取する。Subsequently, the mixture is separated into a methanol-water layer and a chloroform layer using a centrifuge.
次に、メタノール−水層に、アンバーライト陽イオン交
換樹脂を加える。Next, Amberlite cation exchange resin is added to the methanol-water layer.
得られた上澄液に、メタノール性ＮＨ４ＱＨを添加して
中和する。The obtained supernatant liquid is neutralized by adding methanolic NH4QH.
更に濃縮した後、メタノール−水（１０・９）の混合液
を加えて溶解し、該液を検液とする。After further concentration, a mixed solution of methanol-water (10.9) is added and dissolved, and this solution is used as a test solution.
次に、ＥＳ−ＡＰ−３をホスホリパーゼＣによる酵素処
理を行う。Next, ES-AP-3 is subjected to enzyme treatment with phospholipase C.
即ちＥＳ−ＡＰ−３に、Ｏ，ＬＭ）リス緩衝液に溶解し
た０、０１■のホスホリパーゼＣを加え、２７℃で３時
間反応させる。That is, 0.01 μg of phospholipase C dissolved in O, LM) Lis buffer is added to ES-AP-3 and reacted at 27° C. for 3 hours.
終了後、有機層を蒸発させ、更にメタノールクロロホル
ム−水混合液を添加する。After completion, the organic layer is evaporated and a methanol chloroform-water mixture is added.
その後、遠心分離機で分取したメタノール−水層とクロ
ロホルム層を各々検液とする。Thereafter, the methanol-water layer and chloroform layer separated using a centrifuge are used as test solutions.
次に、上述の如くにして、得られた検波で、具体的にラ
ットによる血圧測定について説明する。Next, blood pressure measurement in rats using the detection obtained as described above will be specifically explained.
１）自然発症高血圧ラットを飼育し、収縮期血圧が１６
５ ｘＨ１ｒ以上に達したラットを用いる。1) Spontaneously hypertensive rats were bred and their systolic blood pressure was 16.
Rats that have reached 5xH1r or higher are used.
２）血圧測定はプレチスモクラフ法で非観血的に尾動脈
収縮期の血圧を調べ検液は３３％プロピレングリコール
溶液にけん濁し経口投与する。2) Blood pressure is measured non-invasively by the plethysmograph method, and the blood pressure in the systolic phase of the caudal artery is determined, and the test liquid is suspended in a 33% propylene glycol solution and administered orally.
以下数例の実施例を列挙する。Several examples are listed below.
（実施例第１）
ＥＳ−ＡＰをＫｉ ｅｓｅ Ｉｇｅ １５ＱＧ−３１１
ｉｃａゲル６０（４：１）の混合物をカラムに充填し、
クロロホルム−メタノール−水（１３゜：５０：８）の
混合液を移動相として用いる。(Example 1) Kiose Ige 15QG-311 with ES-AP
Fill the column with a mixture of ica gel 60 (4:1),
A mixture of chloroform-methanol-water (13°:50:8) is used as the mobile phase.
精製されたＥＳ−ＡＰ−３は燐酸塩を含有するが窒素は
含まない。Purified ES-AP-3 contains phosphate but no nitrogen.
該ＥＳ−ＡＰ−３をｕ記うｙトに２．０ｎｇ／ｋｇを経
口投与すると下表の結果が得られた。When 2.0 ng/kg of the ES-AP-3 was orally administered to patients indicated in u, the results shown in the table below were obtained.
ｙ法を用いる）
（いずれもｔ−ｔｅｓｔはＰ（０，０１で有意差〉上表
で明らかな様にＥＳ−ＡＰ−３は有意の差で血圧降下作
用を示す物質であることを示すものである。(Using the y method) (In both cases, the t-test is P (significant difference at 0.01)> As is clear from the table above, ES-AP-3 has a significant difference, indicating that it is a substance that exhibits a blood pressure lowering effect. It is.
（実施例第２）
ＥＳ−ＡＰ−３の化学構造を調査するため、赤外吸収ス
ペクトルを測定すると、グリセロール型脂質に認められ
る１７３６ａｎ−１と長い脂肪鎖の存在を示す２９２８
ｃ、−１と２８５６ ａＬｌ−’に各々強い吸収帯が見
られる。(Example 2) In order to investigate the chemical structure of ES-AP-3, infrared absorption spectra were measured. 1736an-1, which is observed in glycerol-type lipids, and 2928, which indicates the presence of a long fatty chain.
Strong absorption bands are observed at c, -1 and 2856 aLl-'.
（実施例第３）
前記、検液を乾燥させＣＤ（４，に溶解し“８Ｈ核磁気
共鳴で分析し次の値を得る。(Example 3) The test solution was dried, dissolved in CD (4), and analyzed by 8H nuclear magnetic resonance to obtain the following values.
（この測定にはｃｏｓｙ及びｒｅｌａｙ ｃｏｓまた
１３ｃｍＮＭＲ測定でつぎの結果を得る。(For this measurement, the following results are obtained by using cozy and relay cos and 13cm NMR measurements.
（実施例第４）
ＦＤ−質量分析（Ｍ Ｓ 、）を行うとつぎの値が得ら
れる。(Example 4) When FD-mass spectrometry (MS, ) is performed, the following values are obtained.
８８０（８７９）、６１６，５９８．及び以上の結果に
より、マイタケ中に存在する血圧降下作用を有する物質
の構造は、次の一般式で示される窒素を含有しない燐酸
脂質類似の新規化合物である、と結論される。880(879), 616,598. Based on the above results, it is concluded that the structure of the substance present in Maitake mushrooms that has a blood pressure lowering effect is a novel compound similar to a phospholipid that does not contain nitrogen and is represented by the following general formula.
８２Ｃ−０−Ｃ Ｃ−０ −Ｒ２ ２Ｃ −Ｐ −Ｒ３ あり二重結合を１または２個含有する。82C-0-C C-0 -R2 2C -P -R3 Contains one or two double bonds.
Ｒａ： （ＣＨ２）’ＯＣＨ＆
［］
（発明の作用効果）
上述の如〈従来より見出だされている、血圧降下作用を
示し得る燐酸脂質類似化合物は、窒素を含有するが、本
願発明の物質（ＥＳ−ＡＰ−３）には、全く窒素が存せ
ず、経口投与法のみならず、注射法によっても、速やか
に高血圧値を低下させると共に、経時的持続性を有し、
副作用が存在しなく、さらに、低い方の血圧値には何等
の影響も及ぼさない高血圧症に極めて有効な新規化合物
の提供である。Ra: (CH2)'OCH& [] (Actions and Effects of the Invention) As mentioned above, phospholipid-like compounds that have been found in the past and can exhibit a blood pressure lowering effect contain nitrogen, but the substance of the present invention (ES-AP-3) does not contain any nitrogen, rapidly lowers high blood pressure levels not only by oral administration but also by injection, and has a long-lasting effect over time.
The object of the present invention is to provide a novel compound that is extremely effective against hypertension, has no side effects, and has no effect on lower blood pressure values.
特許出願人 コルメディアジャパン株式会社代表取締役
河 内 晟 好Patent Applicant: Cormedia Japan Co., Ltd. Representative Director Akira Kawauchi
Claims (1)
質中に窒素を含有しないことを特徴とする血圧降下作用
を有する窒素を含有しない燐脂質類似化合物の製造方法A method for producing a nitrogen-free phospholipid-like compound having a blood pressure lowering effect, which comprises extracting maitake fruiting bodies and mycelia with an organic solvent and containing no nitrogen in the extracted material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2185246A JP3072302B2 (en) | 1990-07-16 | 1990-07-16 | Method for producing nitrogen-free phospholipid analog having hypotensive action |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2185246A JP3072302B2 (en) | 1990-07-16 | 1990-07-16 | Method for producing nitrogen-free phospholipid analog having hypotensive action |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0474131A true JPH0474131A (en) | 1992-03-09 |
| JP3072302B2 JP3072302B2 (en) | 2000-07-31 |
Family
ID=16167450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2185246A Expired - Lifetime JP3072302B2 (en) | 1990-07-16 | 1990-07-16 | Method for producing nitrogen-free phospholipid analog having hypotensive action |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3072302B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0984551A (en) * | 1995-09-25 | 1997-03-31 | Ryoichi Yamakawa | Grifola frondasa extract free from characteristic odor |
| JP2009184948A (en) * | 2008-02-05 | 2009-08-20 | Rikomu:Kk | HUMAN ADRENERGIC beta3-RECEPTOR AGONIST AGENT, FOOD, AND PHARMACEUTICAL COMPRISING THE SAME |
-
1990
- 1990-07-16 JP JP2185246A patent/JP3072302B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0984551A (en) * | 1995-09-25 | 1997-03-31 | Ryoichi Yamakawa | Grifola frondasa extract free from characteristic odor |
| JP2009184948A (en) * | 2008-02-05 | 2009-08-20 | Rikomu:Kk | HUMAN ADRENERGIC beta3-RECEPTOR AGONIST AGENT, FOOD, AND PHARMACEUTICAL COMPRISING THE SAME |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3072302B2 (en) | 2000-07-31 |
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