JPS6210977B2 - - Google Patents
Info
- Publication number
- JPS6210977B2 JPS6210977B2 JP9386279A JP9386279A JPS6210977B2 JP S6210977 B2 JPS6210977 B2 JP S6210977B2 JP 9386279 A JP9386279 A JP 9386279A JP 9386279 A JP9386279 A JP 9386279A JP S6210977 B2 JPS6210977 B2 JP S6210977B2
- Authority
- JP
- Japan
- Prior art keywords
- acetate
- acetic acid
- formula
- dihydroxyaluminum
- salt
- 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.)
- Expired
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- HDVDLQFPDLTOSI-UHFFFAOYSA-L O[AlH]O Chemical class O[AlH]O HDVDLQFPDLTOSI-UHFFFAOYSA-L 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 2
- 229910018626 Al(OH) Inorganic materials 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 6
- 231100000397 ulcer Toxicity 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HPOYZGTYWKRTPU-DHZHZOJOSA-N (4e)-5,9-dimethyldeca-4,8-dienoic acid Chemical compound CC(C)=CCC\C(C)=C\CCC(O)=O HPOYZGTYWKRTPU-DHZHZOJOSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 4
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 4
- 229960000905 indomethacin Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NHYSRKKHKHCRGR-RFRQLJORSA-N [(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl] acetate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COC(C)=O NHYSRKKHKHCRGR-RFRQLJORSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal salt Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 239000003699 antiulcer agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical class CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 229940000033 dermatological agent Drugs 0.000 description 1
- 239000003241 dermatological agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は下記式（）
（式中ｎは１〜３の整数である）で示される置
換酢酸のジヒドロキシアルミニウム塩、具体的に
はゲラニル酢酸、フアルネシル酢酸またはゲラニ
ルゲラニル酢酸のジヒドロキシアルミニウム塩お
よびその製法に関する。
ゲラニル酢酸およびフアルネシル酢酸の誘導体
は、医薬としての有用性の面からアルカノールエ
ステル、テルペンアルコールエステル等のエステ
ルに関して多くの検討がなされているが〔たとえ
ば特公昭39―5619号、同48―31088号、特開昭49
―43917号、同50―29518号等〕、本発明の如きア
ルミニウムを含有するゲラニル酢酸およびフアル
ネシル酢酸の誘導体は知られていない。
本発明において式（）で示される置換酢酸の
ジヒドロキシアルミニウム塩は、下記式（）で
示される置換酢酸のアルカリ金属塩と下記式
（）で示されるアルミニウム化合物とを反応さ
せることにより容易に製造することができる。
上記式においてｎは前記定義であり、Ｍはリチ
ウム、カリウム、ナトリウム等のアルカリ金属を
表わし、Ｘは塩素、臭素、ヨウ素等のハロゲン原
子を表わす。式（）の化合物および式（）の
化合物は水溶性であるが、式（）の化合物は水
に難溶であるので、上記反応は原料化合物のそれ
ぞれの水溶液を混合することによつて瞬時に進行
し、生成物が沈殿となつて得られる。反応に際し
て加熱および冷却は特に必要なく、また雰囲気も
普通の大気でよい。生成物は過により単離でき
る。
本発明によるジヒドロキシアルミニウム塩は、
ゲラニル酢酸またはフアルネシル酢酸のエステル
と同様の用途、たとえば抗潰瘍剤、皮膚病薬とし
ての有用性を有する。とくにフアルネシル酢酸の
ジヒドロキシアルミニウム塩は高い抗潰瘍活性を
有することに加えて、ラツトに対する8.0ｇ/Kg以
上の多量投与でも全く毒性を示さないという驚く
べき低毒性を有する。したがつて該化合物は、比
較的長期間にわたつて投与される抗潰瘍剤として
極めて好適である。この点について次に具体的に
説明する。
抗潰瘍作用（インドメタシン潰瘍に対して）
雄性ドンリユー系ラツト（210〜230ｇ）を24時
間絶食させたのち、１％CMC液に懸濁したイン
ドメタシン（メルク社製）を20mg/Kgの量で皮下
に投与した。７時間後にラツトをエーテル致死さ
せ、胃の粘膜部に発生したインドメタシン誘起潰
瘍の長さ（mm）を測定した。一匹あたりの潰瘍の
長さの合計を潰瘍係数とする。検体およびゲフア
ルネートはインドメタシン投与の10分前にそれぞ
れ経口投与した。コントロール群と検体投与群と
の潰瘍係数の差をコントロール群の潰瘍係数で除
して抑制率を算出した。結果は次のとおりであつ
た。
The present invention is based on the following formula () The present invention relates to a dihydroxyaluminum salt of a substituted acetic acid represented by the formula (in which n is an integer of 1 to 3), specifically a dihydroxyaluminum salt of geranyl acetic acid, pharnesyl acetic acid, or geranylgeranylacetic acid, and a method for producing the same. Regarding derivatives of geranyl acetic acid and phalnesyl acetic acid, many studies have been conducted on esters such as alkanol esters and terpene alcohol esters from the viewpoint of their usefulness as medicines [for example, Japanese Patent Publication Nos. 39-5619, 48-31088, Japanese Patent Application Publication 1973
No. 43917, No. 50-29518, etc.], and derivatives of geranyl acetic acid and phalnesylacetic acid containing aluminum such as those of the present invention are not known. In the present invention, the dihydroxyaluminum salt of substituted acetic acid represented by the formula () is easily produced by reacting the alkali metal salt of substituted acetic acid represented by the following formula () with an aluminum compound represented by the following formula (). be able to. In the above formula, n is as defined above, M represents an alkali metal such as lithium, potassium, or sodium, and X represents a halogen atom such as chlorine, bromine, or iodine. The compound of formula () and the compound of formula () are water-soluble, but the compound of formula () is sparingly soluble in water, so the above reaction can be carried out instantly by mixing aqueous solutions of each of the raw material compounds. The reaction proceeds and the product is obtained as a precipitate. Heating and cooling are not particularly required during the reaction, and the atmosphere may be normal air. The product can be isolated by filtration. The dihydroxyaluminum salt according to the invention is
It has similar uses as esters of geranyl acetate or phalnesyl acetate, such as antiulcer agents and dermatological agents. In particular, the dihydroxyaluminum salt of phalnesylacetic acid has not only high antiulcer activity but also surprisingly low toxicity, showing no toxicity at all even when administered to rats in large doses of 8.0 g/Kg or more. The compound is therefore highly suitable as an anti-ulcer agent administered over a relatively long period of time. This point will be specifically explained next. Anti-ulcer effect (indomethacin against ulcers) After fasting male Donrieux rats (210-230 g) for 24 hours, indomethacin (manufactured by Merck & Co., Ltd.) suspended in 1% CMC solution was administered subcutaneously at a dose of 20 mg/Kg. administered. Seven hours later, the rats were sacrificed with ether, and the length (mm) of indomethacin-induced ulcers that had developed on the gastric mucosa were measured. The total length of ulcers per animal is the ulcer coefficient. The specimen and gephalnate were each orally administered 10 minutes before indomethacin administration. The inhibition rate was calculated by dividing the difference in ulcer coefficient between the control group and the sample administration group by the ulcer coefficient of the control group. The results were as follows.
【表】
＊ ジヒドロキシアルミニウムフアルネシ
ルアセテート
急性毒性
５週令のウイスター系ラツトを１週間予備飼育
したのち、１群５匹として、フアルネシル酢酸ジ
ヒドロキシアルミニウム塩を経口投与した。２週
間の観察期間中、該アルミニウム塩をそれぞれ
6.0ｇ/Kgおよび8.0ｇ/Kg投与したいずれの群にお
いても死亡例はなく、観察終了時の剖検によつて
も異常は認められなかつた。
実施例 １
フアルネシル酢酸26.4ｇと10％水酸化ナトリウ
ム水溶液40ｇとを反応させてフアルネシル酢酸ナ
トリウムの水溶液を調製した。別にアルミニウム
粉末2.7ｇと３規定の塩酸34mlとを70〜80℃に加
熱してClAl（OH）2の水溶液を調製し、これを前
記のフアルネシル酢酸ナトリウムの水溶液に加え
て、生成した白色沈殿を過した。分離した沈殿
を水洗したのち減圧下に加熱、乾燥して、32.1ｇ
の白色粉末を得た。このものは赤外線吸収スペク
トルおよび元素分析によりジヒドロキシアルミニ
ウムフアルネシルアセテートであることが確認さ
れた。[Table] * Acute toxicity of dihydroxyaluminum phalnesyl acetate After 5-week-old Wistar rats were preliminarily housed for one week, dihydroxyaluminum phalnesyl acetate salt was orally administered to each group of 5 rats. During the 2-week observation period, each of the aluminum salts
There were no deaths in either the 6.0g/Kg or 8.0g/Kg administration groups, and no abnormalities were observed in autopsy at the end of the observation. Example 1 An aqueous solution of sodium pharnesyl acetate was prepared by reacting 26.4 g of pharnesylacetic acid with 40 g of a 10% aqueous sodium hydroxide solution. Separately, prepare an aqueous solution of ClAl(OH) 2 by heating 2.7 g of aluminum powder and 34 ml of 3N hydrochloric acid to 70-80°C, and add this to the aqueous solution of sodium pharnesyl acetate to remove the white precipitate. passed. The separated precipitate was washed with water and then heated and dried under reduced pressure to give 32.1g.
A white powder was obtained. This product was confirmed to be dihydroxyaluminum phalnesyl acetate by infrared absorption spectrum and elemental analysis.
【表】
実施例 ２
ゲラニル酢酸19.6ｇと10％水酸化ナトリウム水
溶液40ｇとを反応させてゲラニル酢酸ナトリウム
の水溶液を調製した。別に調製したClAl（OH）2
の水溶液（3.2モル／）31mlを前記ゲラニル酢
酸ナトリウムの水溶液に加えて生成した白色沈殿
を過した。分離した沈殿を水洗したのち減圧下
に加熱、乾燥して26.2ｇの白色粉末を得た。この
ものは赤外線吸収スペクトルおよび元素分析によ
り、ジヒドロキシアルミニウムゲラニルアセテー
トであることが確認された。[Table] Example 2 An aqueous solution of sodium geranyl acetate was prepared by reacting 19.6 g of geranyl acetic acid with 40 g of a 10% aqueous sodium hydroxide solution. Separately prepared ClAl(OH) 2
31 ml of an aqueous solution (3.2 mol/) was added to the aqueous solution of sodium geranyl acetate, and the white precipitate formed was filtered. The separated precipitate was washed with water and then heated and dried under reduced pressure to obtain 26.2 g of white powder. This product was confirmed to be dihydroxyaluminum geranyl acetate by infrared absorption spectrum and elemental analysis.
【表】【table】
【表】
実施例 ３
ゲラニルゲラニル酢酸3.33ｇをメタール20mlに
溶かし、５％水酸化ナトリウム８ｇと反応させて
ゲラニルゲラニル酢酸ナトリウムの水―メタノー
ル溶液を調製した。別に調製したClAl（OH）2の
水溶液（3.2モル／）3.1mlを前記ゲラニルゲラ
ニル酢酸ナトリウムの水―メタノール溶液に加
え、生成した白色沈殿を過した。分離した沈殿
を水洗したのち減圧下に加熱、乾燥して3.48ｇの
白色粉末を得た。このものは赤外線吸収スペクト
ルおよび元素分析によりジヒドロキシアルミニウ
ムゲラニルゲラニルアセテートであることが確認
された。[Table] Example 3 3.33 g of geranylgeranyl acetate was dissolved in 20 ml of metal and reacted with 8 g of 5% sodium hydroxide to prepare a water-methanol solution of sodium geranylgeranyl acetate. 3.1 ml of a separately prepared aqueous solution of ClAl(OH) 2 (3.2 mol/) was added to the water-methanol solution of sodium geranylgeranyl acetate, and the white precipitate formed was filtered. The separated precipitate was washed with water and then heated and dried under reduced pressure to obtain 3.48 g of white powder. This product was confirmed to be dihydroxyaluminumgeranylgeranyl acetate by infrared absorption spectrum and elemental analysis.
Claims (1)
換酢酸のジヒドロキシアルミニウム塩。 ２ 下記式() （式中Ｍはアルカリ金属を表わし、ｎは１〜３
の整数である）で示される置換酢酸のアルカリ金
属塩と下記式（） Ｘ−Al（OH）2 () （式中Ｘはハロゲン原子を表わす）で示される
化合物とを反応させることを特徴とする置換酢酸
のジヒドロキシアルミニウム塩の製法。[Claims] 1 The following formula () A dihydroxyaluminum salt of substituted acetic acid represented by the formula (wherein n is an integer of 1 to 3). 2 The following formula () (In the formula, M represents an alkali metal, and n is 1 to 3
is an integer of ) and a compound represented by the following formula () X-Al(OH) 2 () (where X represents a halogen atom). A method for producing dihydroxyaluminum salt of substituted acetic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9386279A JPS5618933A (en) | 1979-07-23 | 1979-07-23 | Dihydroxy aluminum salt of substituted acetic acid and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9386279A JPS5618933A (en) | 1979-07-23 | 1979-07-23 | Dihydroxy aluminum salt of substituted acetic acid and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5618933A JPS5618933A (en) | 1981-02-23 |
| JPS6210977B2 true JPS6210977B2 (en) | 1987-03-10 |
Family
ID=14094241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9386279A Granted JPS5618933A (en) | 1979-07-23 | 1979-07-23 | Dihydroxy aluminum salt of substituted acetic acid and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5618933A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0572050U (en) * | 1992-03-02 | 1993-09-28 | 矢崎総業株式会社 | Resistance welding terminal |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1391292A (en) * | 1971-08-03 | 1975-04-23 | Polaroid Corp | Photographic exposure control systems |
| US4996551A (en) * | 1989-02-20 | 1991-02-26 | Fuji Photo Film Co., Ltd. | Exposure control apparatus |
-
1979
- 1979-07-23 JP JP9386279A patent/JPS5618933A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0572050U (en) * | 1992-03-02 | 1993-09-28 | 矢崎総業株式会社 | Resistance welding terminal |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5618933A (en) | 1981-02-23 |
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