JPS6048506B2 - Guanidinobenzoic acid derivatives - Google Patents
Guanidinobenzoic acid derivativesInfo
- Publication number
- JPS6048506B2 JPS6048506B2 JP5989377A JP5989377A JPS6048506B2 JP S6048506 B2 JPS6048506 B2 JP S6048506B2 JP 5989377 A JP5989377 A JP 5989377A JP 5989377 A JP5989377 A JP 5989377A JP S6048506 B2 JPS6048506 B2 JP S6048506B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- compound
- guanidinobenzoic
- guanidinobenzoic acid
- 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
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はグアニジノ安息香酸誘導体、さらに詳しく言え
ば一般式〔Ｉ〕−０ＯＣＣＨ２ＣＨ２０〔Ｉ〕
ことにある。DETAILED DESCRIPTION OF THE INVENTION The present invention resides in guanidinobenzoic acid derivatives, more specifically in general formula [I]-0OCCH2CH20[I].
フ 本発明によれば、一般式〔Ｉ〕で示されるグアニジ
ノ安息香誘導体は一般式〔旧（式中、Ｘはハロゲンを表
わす）
で示される４−グアニジノ安息香酸ハライドと一般式〔
■〕（式中、Ｒ’は水素、ハロゲン、低級アルキル基、
低級アルコキシ基、保護アミノ基、低級アルコキシカル
ボニル基、ニトロ基、アシルアミノ基を表わす）で示さ
れる化合物を脱ハロゲン化水素剤の存在下に反応させ、
Ｒ’が保護アミノ基を表わす場合には保護基を脱離させ
ることによつて製造することができる。According to the present invention, the guanidinobenzoic acid derivative represented by the general formula [I] is combined with the 4-guanidinobenzoic acid halide represented by the general formula [formula (wherein, X represents a halogen)] and the general formula [
■〕(In the formula, R' is hydrogen, halogen, lower alkyl group,
(representing a lower alkoxy group, a protected amino group, a lower alkoxycarbonyl group, a nitro group, an acylamino group) in the presence of a dehydrohalogenating agent,
When R' represents a protected amino group, it can be produced by removing the protecting group.
本発明で使用する原料化合物〔■〕は４−グアニジノ安
息香酸から通常の方法で得ることができる。The starting compound [■] used in the present invention can be obtained from 4-guanidinobenzoic acid by a conventional method.
簡単にはチオニルクロライドと加温することによつて製
造でき、この場合塩酸塩として得られ、このまま使用す
る。又原料化合物゛〔■〕は一般式〔■〕
（式中、Ｒ’は前記の意味を表わす）
で示される化合物をチオニルクロライド、五塩化リンな
どを用いる通常の方法によつて対応する酸ハライドとし
た後、ピリジン中又はエーテル、ベンゼン、アセトニト
リル、テトラヒドロフランの如き有機溶媒中トリエチル
アミン、トリブチルアミン、ジメチルアニリン、ピリジ
ンなどの脱ハロゲン化水素剤の存在下にハイドロキノン
（等モル〜５倍モル）と０℃〜室温で１〜５時間反応さ
せることによつて得られる。It can be easily produced by heating with thionyl chloride, in which case it is obtained as a hydrochloride and used as is. In addition, the raw material compound ゛[■] is prepared by converting the compound represented by the general formula [■] (in the formula, R' represents the above meaning) into the corresponding acid halide by a conventional method using thionyl chloride, phosphorus pentachloride, etc. Then, in the presence of a dehydrohalogenating agent such as triethylamine, tributylamine, dimethylaniline, or pyridine in pyridine or an organic solvent such as ether, benzene, acetonitrile, or tetrahydrofuran, hydroquinone (equimolar to 5 times the molar amount) and 0 It is obtained by reacting for 1 to 5 hours at a temperature of .degree. C. to room temperature.
一般式〔■〕て表わされる化合物で例えばＲ’がｐ−ニ
トロ、ｐ−アセトアミノ基である化合物はアナーレ．ト
ウ．シミー（バリ）〔Ａｎｎ．Ｃｈｌｍ（ＰａｒｌＳ）
〕〔１３〕２，５８７（１９５７）に、Ｒ’がｐ−メチ
ル基である化合物はモナートシエフテ．ピュアー．ヘミ
（ＭＯｎａｔｒｈ．Ｃｈｅｍ）８８．５１７（１９５
７）にＲ’がｍ−メトキシ基である化合物はジャーナル
．オブ゛．ジ．アメリカンケミカルソサエ５テイ（Ｊ．
Ａｍ．Ｃｈｅｍ．Ｓｃｃ．）７４．２２５１（１９５２
）に記載載された方法により得られる。Among the compounds represented by the general formula [■], for example, the compounds in which R' is p-nitro or p-acetamino group are anale. Tow. Shimmy (Bali) [Ann. Chlm(ParlS)
] [13] 2,587 (1957), a compound in which R' is a p-methyl group is described by Monart Schieft. Pure. Hemi (MOnatrh.Chem) 88.517 (195
The compound in which R' is m-methoxy group in 7) is described in Journal. Of. J. American Chemical Society 5 (J.
Am. Chem. Scc. )74.2251 (1952
) can be obtained by the method described in .
又Ｒ’が保護アミノ基である化合物はｐ−アミノフェニ
ルプロピオン酸〔ジャーナル．オブ．ジ．アメリカン
ケミカルソサエテイ８１４６３９（１９５９）〕のアミ
ノ基をア′θミノ保護基、例えばベンジルオキシカルボ
ニル、第三級プトキシカルボニル、第Ξ級アミルオキシ
カルボニル基などで保護することにより得られる。本発
明を実施するにあたつては上記原料化合物５〔■〕を溶
媒に溶かし、脱ハロゲン化水素剤の存在下に上記原料化
合物〔■〕を加えて反応を行なう。A compound in which R' is a protected amino group is p-aminophenylpropionic acid [Journal. of. J. American
Chemical Society 814639 (1959)] by protecting the amino group with an amino-protecting group such as benzyloxycarbonyl, tertiary ptoxycarbonyl, Ξ-class amyloxycarbonyl group, etc. In carrying out the present invention, the above-mentioned starting compound 5 [■] is dissolved in a solvent, and the above-mentioned starting compound [■] is added in the presence of a dehydrohalogenating agent to carry out the reaction.
上記の反応はハロゲン化水素を副生する縮合反応であり
、脱ハロゲン化水素剤例えばトリエチルクアミン、トリ
ブチルアミン、ジメチルアニリン、ピリジン等の第三級
有機アミンの存在下で行なうのが有利である。The above reaction is a condensation reaction that produces hydrogen halide as a by-product, and is advantageously carried out in the presence of a dehydrohalogenating agent, such as a tertiary organic amine such as triethylquamine, tributylamine, dimethylaniline, or pyridine. .
使用できる溶媒としてはベンゼン、トルエン、エーテル
、テトラヒドロフラン、ジオキサン、ア７セトニトリル
、ピリジン等があり前述のようにピリジンは脱ハロゲン
化水素剤としても作用するので特に好ましいものである
。Usable solvents include benzene, toluene, ether, tetrahydrofuran, dioxane, acetonitrile, and pyridine, and as mentioned above, pyridine is particularly preferred since it also acts as a dehydrohalogenating agent.
反応を実施するにあたつては上記原料化合物〔■〕を溶
媒好ましくはピリジンに溶解し、このＪ溶液中に原料化
合物〔■〕を加えて攪拌すればよい。In carrying out the reaction, the above starting compound [■] may be dissolved in a solvent, preferably pyridine, and the starting compound [■] may be added to this J solution and stirred.
この反応は比較的容易に進行するので０℃ないし室温で
３吟から３時間攪拌すればよい。目的化合物〔Ｉ〕はハ
ロゲン化水素との塩の形で生成する。この目的化合物〔
Ｉ〕を分取するにあたつては反応液中に重炭酸ナトリウ
ムの水溶液を加えれば目的化合物が炭酸塩の結晶として
得られる。一般式〔Ｉ〕の化合物でＲがアミノ基である
化合物を得るには、一般式〔■〕でＲ’保護アミノ基で
ある化合物を用いて一般式〔■〕の化合物と上述の如く
反応させた後、アミノ保護基を脱離させればよい。Since this reaction proceeds relatively easily, it may be stirred at 0° C. to room temperature for 3 to 3 hours. The target compound [I] is produced in the form of a salt with hydrogen halide. This target compound [
[I]], by adding an aqueous solution of sodium bicarbonate to the reaction solution, the target compound can be obtained as carbonate crystals. To obtain a compound of general formula [I] in which R is an amino group, a compound of general formula [■] in which R' is a protected amino group is reacted with a compound of general formula [■] as described above. After that, the amino protecting group may be removed.
これらのアミノ保護基の脱離には通常用いられている方
法に従つて処理すればよい。また別の方法として一般式
〔Ｉ〕でＲがニトロ基である化合物を有機溶媒例えばア
ルコール中で酸化白金、パラジウム炭素、又はラネーニ
ツケルを触媒として接触還元することによつても得るこ
とができる。得られた目的化合物は更に所望によつて塩
酸、硫酸、リン酸、臭化水素酸等の無機酸の塩、あるい
は酢酸、プロピオン酸、乳酸、マレイン酸、フマル酸、
酒石酸、クエン酸、メタンスルホン酸、ベンゼンスルホ
ン酸、トルエンスルホン酸等の有機酸の塩に変換できる
。These amino protecting groups can be removed by a commonly used method. Alternatively, it can be obtained by catalytically reducing a compound of general formula [I] in which R is a nitro group in an organic solvent such as alcohol using platinum oxide, palladium on carbon, or Raney nickel as a catalyst. The obtained target compound may be further treated with a salt of an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, or hydrobromic acid, or acetic acid, propionic acid, lactic acid, maleic acid, fumaric acid, etc., as desired.
It can be converted into salts of organic acids such as tartaric acid, citric acid, methanesulfonic acid, benzenesulfonic acid, and toluenesulfonic acid.
本発明によつて得られる化合物は文献末記載の新規化合
物であり、蛋白質分解酵素のトリプシンやａ−キモトリ
プシンを阻害する作用を有しており、これらの阻害作用
は極めて低い濃度て強く現われた。The compound obtained by the present invention is a novel compound described at the end of the literature, and has the effect of inhibiting trypsin and a-chymotrypsin, which are proteolytic enzymes, and these inhibitory effects were strongly exhibited at extremely low concentrations.
これらの阻害作用は第１表に示す如くである。化合物１
化合物２
トリプシン阻害作用は村松等、ザ．ジヤーヅル．オブ．
バイオケミストリー（ＴｈｅＪＯｕｍａＯｆＢｌＯｃｈ
ｅｍｉｓｔｒｙ），５８，２１４（１９６４）、ａ−キ
モトリプシン阻害作用は村松等，同種，６２，４０１（
１９６７）記載の方法を参考にして測定した。These inhibitory effects are shown in Table 1. Compound 1 Compound 2 The trypsin inhibitory effect was reported by Muramatsu et al., The. Jaguar crane. of.
Biochemistry (TheJOumaOfBlOch
emistry), 58, 214 (1964), a-chymotrypsin inhibitory effect was reported by Muramatsu et al.
The measurements were made with reference to the method described in (1967).
表叶のトリプシン阻害作用は３ＴＣ，３吟間の反応でト
リプシン０．５ｐｇがｐ−トシルアルギニンメチノレエ
ステルを水解する作用を５０％抑制する化合物１及び２
の濃度を表わしたものであり、ａ−キモトリプシン２ｐ
ｇがＮ−アセチルーＬ−チロシンゴチルエステルを水解
する作用を５０％抑制する化泊物１及び２の濃度を表わ
したものである。このように本発明化合物はトリプシン
に対して強い阻害作用を有するほか、ａ−キモトリプシ
ンに対しても、これ迄に知られているトラジロー几（牛
臓器から抽出した蛋白質分解酵素阻害作用ｋ有するペプ
タイドバイエル社製）やキモスタチン（微生物が産生す
るペプタイド）などと異なる袢く新らしい形の阻害物質
である点注目に値いするものであり、急性膵炎等膵臓性
疾患治療剤など１医薬用途として有用なものである。The trypsin inhibitory effect of Omoteko is 3TC, Compounds 1 and 2 which suppress the hydrolyzing effect of 0.5 pg of trypsin on p-tosylarginine methylenyl ester by 50% in the 3-gin reaction.
It represents the concentration of a-chymotrypsin 2p.
g represents the concentration of compounds 1 and 2 that inhibits the action of hydrolyzing N-acetyl-L-tyrosine Gotyl ester by 50%. In this way, the compound of the present invention not only has a strong inhibitory effect on trypsin, but also has a strong inhibitory effect on a-chymotrypsin compared with the previously known Torajiro-Kan (a peptide Bayer extract extracted from bovine organs that has a protease inhibitory effect). It is noteworthy that it is a new type of inhibitor that differs from chymostatin (a peptide produced by microorganisms) and chymostatin (a peptide produced by microorganisms), and is useful as a drug for medical purposes such as a treatment for pancreatic diseases such as acute pancreatitis. It is something.
以下、実施例により本発明を説明するが、本溌明はこれ
らに限定されるものではない。The present invention will be explained below with reference to Examples, but the present invention is not limited thereto.
実施例１
４−グアニジノ安息香酸−４”−（フェニルプロピオニ
ルオキシ）フェニルエステル４−グアニジノ安息香酸１
．２５ｇにチオニルクロライド１０ｇを加えて３吟間加
熱還流させて４−グアニジノ安息香酸クロライド、塩酸
塩を得た。Example 1 4-guanidinobenzoic acid-4”-(phenylpropionyloxy)phenyl ester 4-guanidinobenzoic acid 1
．． 10 g of thionyl chloride was added to 25 g and heated under reflux for 3 minutes to obtain 4-guanidinobenzoic acid chloride, hydrochloride.
これを４−（フェニルプロピオニルオキシ）フエノーノ
レ１．０９ｇをピリジン５ｍ１に溶かした溶液中にＯ′
Ｃで加え徐々に温度を上げ室温で２時間攪拌した。This was added to a solution of 1.09 g of 4-(phenylpropionyloxy)phenol dissolved in 5 ml of pyridine.
The temperature was gradually raised and the mixture was stirred at room temperature for 2 hours.
その後反応液中に飽和の重炭酸ソーダ水溶液を加えて析
出してきた結晶を戸取した。水、アセトンで洗浄し乾燥
して粗製の目的化合物の炭酸塩１．４ｇ（融点１２９〜
１３３゜Ｃ）を得た。これをエタノールに懸濁させてメ
タンスルホン酸を加えて弱酸性とし、室温で溶解させ、
活性炭を加えて胛過し胛液を減圧濃縮し、これにエーテ
ルを加えて放置した、析出した結晶を胛取し、再生エタ
ノ−ルーエーテルから精製して融点１６５〜１６８−ｃ
のメタンスルホン酸塩の結晶９３０ｍｇを得た。元素分
析値：Ｃ。Thereafter, a saturated aqueous sodium bicarbonate solution was added to the reaction solution, and the precipitated crystals were collected. Washed with water and acetone and dried to obtain 1.4 g of crude carbonate of the target compound (melting point 129~
133°C) was obtained. Suspend this in ethanol, add methanesulfonic acid to make it weakly acidic, dissolve it at room temperature,
Activated carbon was added and filtered, and the liquid was concentrated under reduced pressure. Ether was added to this and left to stand. The precipitated crystals were collected and purified from recycled ethanol-ether to give a melting point of 165-168-c.
930 mg of methanesulfonate crystals were obtained. Elemental analysis value: C.
。Ｈ２，Ｎ。Ｏ。・ＣＨ３ＳＯ。Ｈとして４−グアニジ
ノ安息香酸−４’一（４ −クロロフェニルプロピオニ
ルオキシ）フェニルエステル実施例１と同様にして４−
グアニジノ安息香酸１．２５ｇを酸クロライド塩酸塩と
し、これを４一（４’−クロロフェニルプロピオニルオ
キシ）フエノーノレ１．３９ｇのピリジン溶液にｏ℃で
加えて２時間反応させ、実施例１と同様に後処理して目
的化合物のメタンスルホン酸塩１．０１ｇを得た。. H2,N. O.・CH3SO. H is 4-guanidinobenzoic acid-4'-(4-chlorophenylpropionyloxy)phenyl ester in the same manner as in Example 1.
1.25 g of guanidinobenzoic acid was converted into acid chloride hydrochloride, and this was added to a pyridine solution of 1.39 g of 4-(4'-chlorophenylpropionyloxy)phenol at 0°C and reacted for 2 hours. After treatment, 1.01 g of methanesulfonate of the target compound was obtained.
融点：１８２〜１８５゜Ｃ０元素分析値：Ｃ，２Ｈ２Ｏ
ＣｌＮ３Ｏ。Melting point: 182-185° C0 elemental analysis: C, 2H2O
ClN3O.
．ＣＨ３ＳＯ。Ｈとして２ノ＾、″ツＶリ υ実施例１
と同様の反応を行なうことによつて、次の化合物を得た
。．． CH3SO. 2 as H, ``Tsu Vri υExample 1
The following compound was obtained by carrying out the same reaction.
１４−グアニジノ安息香酸−４’− （４−メトキシフ
ェニルプロピオニルオキシ）フェニルエステルメタンス
ルホン酸塩融点：１５６〜１６０℃。14-Guanidinobenzoic acid-4'-(4-methoxyphenylpropionyloxy)phenyl ester methanesulfonate Melting point: 156-160°C.
２４−グアニジノ安息香酸−４’−（４−ニトロフェニ
ルプロピオニルオキシ）フェニルエステルメタンスルホ
ン酸塩融点：１７８℃
３４−グアニジノ安息香酸−４’−（４−アミノフェニ
ルプロピオニルオキシ）フェニルエステルメタンスルホ
ン酸塩融点：１３３〜１３５℃。24-guanidinobenzoic acid-4'-(4-nitrophenylpropionyloxy) phenyl ester methanesulfonate Melting point: 178°C 34-guanidinobenzoic acid-4'-(4-aminophenylpropionyloxy) phenyl ester methanesulfonate Melting point: 133-135°C.
Claims (1)
は水素、ハロゲン、低級アルキル基、低級アルコキシ基
、アミノ基、低級アルコキシカルボニル基、ニトロ基、
アシルアミノ基を表わす）で示される化合物及びその酸
付加塩。 ２ ４−グアニジノ安息香酸−４′−（フェニルプロピ
オニルオキシ）フェニルエステル及びその酸付加塩であ
る特許請求の範囲第１項記載の化合物。 ３ ４−グアニジノ安息香酸−４′−（４−クロロフェ
ニルプロピオニルオキシ）フェニルエステル及びその酸
付加塩である特許請求の範囲第１項記載の化合物。[Claims] 1 General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] (In the formula, R
is hydrogen, halogen, lower alkyl group, lower alkoxy group, amino group, lower alkoxycarbonyl group, nitro group,
(representing an acylamino group) and its acid addition salts. 2. The compound according to claim 1, which is 4-guanidinobenzoic acid-4'-(phenylpropionyloxy)phenyl ester and its acid addition salt. 3. The compound according to claim 1, which is 4-guanidinobenzoic acid-4'-(4-chlorophenylpropionyloxy)phenyl ester and its acid addition salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5989377A JPS6048506B2 (en) | 1977-05-25 | 1977-05-25 | Guanidinobenzoic acid derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5989377A JPS6048506B2 (en) | 1977-05-25 | 1977-05-25 | Guanidinobenzoic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53147044A JPS53147044A (en) | 1978-12-21 |
| JPS6048506B2 true JPS6048506B2 (en) | 1985-10-28 |
Family
ID=13126238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5989377A Expired JPS6048506B2 (en) | 1977-05-25 | 1977-05-25 | Guanidinobenzoic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6048506B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0584345B2 (en) * | 1986-02-13 | 1993-12-01 | Kawasaki Heavy Ind Ltd |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55100356A (en) * | 1979-01-29 | 1980-07-31 | Kowa Co | Benzenediol derivative |
| JPH0764801B2 (en) * | 1985-11-12 | 1995-07-12 | 小野薬品工業株式会社 | p-guanidinobenzoic acid phenyl ester derivative |
| JPH0446148A (en) * | 1990-06-08 | 1992-02-17 | Asahi Chem Ind Co Ltd | 4-guadininobenzoic phenyl ester derivative and protease inhibitor containing the same |
| KR20000005312A (en) | 1996-04-10 | 2000-01-25 | 오노 야꾸힝 고교 가부시키가이샤 | Tryptase inhibitor and novel guanidino derivatives |
-
1977
- 1977-05-25 JP JP5989377A patent/JPS6048506B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0584345B2 (en) * | 1986-02-13 | 1993-12-01 | Kawasaki Heavy Ind Ltd |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53147044A (en) | 1978-12-21 |
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