JPS6340183B2 - - Google Patents
Info
- Publication number
- JPS6340183B2 JPS6340183B2 JP54063685A JP6368579A JPS6340183B2 JP S6340183 B2 JPS6340183 B2 JP S6340183B2 JP 54063685 A JP54063685 A JP 54063685A JP 6368579 A JP6368579 A JP 6368579A JP S6340183 B2 JPS6340183 B2 JP S6340183B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- amidinophenol
- solution
- minutes
- compound
- 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
- IYELGEUXPAPULN-UHFFFAOYSA-N 2-hydroxybenzenecarboximidamide Chemical class NC(=N)C1=CC=CC=C1O IYELGEUXPAPULN-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000007853 buffer solution Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 5
- 102000004142 Trypsin Human genes 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108090000317 Chymotrypsin Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108090000190 Thrombin Proteins 0.000 description 3
- 108090000631 Trypsin Proteins 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229960002376 chymotrypsin Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- -1 inorganic acid salts Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229960004072 thrombin Drugs 0.000 description 3
- 239000012588 trypsin Substances 0.000 description 3
- 229960001322 trypsin Drugs 0.000 description 3
- VDLWTJCSPSUGOA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)CCCC2=C1 VDLWTJCSPSUGOA-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229940122644 Chymotrypsin inhibitor Drugs 0.000 description 2
- 101710137926 Chymotrypsin inhibitor Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003541 chymotrypsin inhibitor Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- TWADEBCIPVNACR-ZDUSSCGKSA-N (2s)-2-(n-(4-methylphenyl)sulfonylanilino)propanoic acid Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N([C@@H](C)C(O)=O)C1=CC=CC=C1 TWADEBCIPVNACR-ZDUSSCGKSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- SKAWDTAMLOJQNK-UHFFFAOYSA-N 2-acetamido-3-(4-hydroxyphenyl)propanoic acid ethyl ester Chemical compound CCOC(=O)C(NC(C)=O)CC1=CC=C(O)C=C1 SKAWDTAMLOJQNK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- FKMJXALNHKIDOD-LBPRGKRZSA-N TAMe Chemical compound NC(=N)NCCC[C@@H](C(=O)OC)NS(=O)(=O)C1=CC=C(C)C=C1 FKMJXALNHKIDOD-LBPRGKRZSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 101000712605 Theromyzon tessulatum Theromin Proteins 0.000 description 1
- 229940122388 Thrombin inhibitor Drugs 0.000 description 1
- 229940122618 Trypsin inhibitor Drugs 0.000 description 1
- 101710162629 Trypsin inhibitor Proteins 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- BKBLNHSNWGHNEZ-UHFFFAOYSA-N methanesulfonic acid;naphthalene-1-carboxylic acid Chemical compound CS(O)(=O)=O.C1=CC=C2C(C(=O)O)=CC=CC2=C1 BKBLNHSNWGHNEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は新規なアミジノフエノール誘導体、更
に詳細には次式（）、
で表わされるアミジノフエノール誘導体に関す
る。
本発明者は種々のアミジノフエノール誘導体を
合成し、その薬理作用を検索していたところ、上
記式（）で表わされるアミジノフエノール誘導
体が種々の蛋白分解酵素、例えばキモトリプシ
ン、トリプシン、スロンビン等に対し阻害作用を
有することを見出し、本発明を完成した。
従つて、本発明は新規なアミジノフエノ−ル誘
導体を提供するものである。
本発明化合物（）は、例えば次の反応に従つ
て、１，２，３，４−テトラヒドロナフタレン−
１−カルボン酸（）にアミジノフエノール
（）を作用させることにより製造される。
１，２，３，４−テトラヒドロナフタレン−１
−カルボン酸（）とアミジノフエノール（）
との反応は、通常のエステル化反応、例えば、
１，２，３，４−テトラヒドロナフタレン−１−
カルボン酸またはその反応性誘導体を直接あるい
は縮合剤の存在下アミジノフエノールまたはその
反応性誘導体と反応させることにより実施され
る。
このようにして得られた化合物（）は、更
に、常法に従つて、例えば塩酸、硫酸、リン酸お
よび臭化水素酸等の無機酸塩；あるいは酢酸、プ
ロピオン酸、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
およびトルエンスルホン酸等の有機酸塩に導くこ
とができる。
斯くして得られた本発明化合物（）の酵素阻
害作用を試験した結果は次の通りである。
(1) キモトリプシン阻害作用
村松らの方法〔ザ・ジヤーナル・オブ・ビオケ
ミストリー62，408（1967）参照〕により、被検化
合物のジメチルスルホキシド溶液0.1ml、水0.1ml
及びキモトリプシン10μｇ／mlの緩衝液溶液
（0.1Mトリス−塩酸緩衝液；PH8.0）0.1mlを混合
した溶液を10分間インキユベートし、これにアセ
チル−Ｌ−チロシンエチルエステル25mMの緩衝
液溶液0.2mlを混合し、37℃で30分間反応させ、
残存する基質の量をヘステリン法により発色さ
せ、530nmの吸光度を測定し求めた。なお比較化
合物として4′−アミジノフエニル シクロヘキサ
ンカルボキシレート（比較化合物１）及びキモト
リプシンの阻害剤として知られるトシルフエニル
アラニンクロロメチルケトン（比較化合物２）を
用いた。
結果は第１表の通りである。
(2) トリプシン阻害作用
村松らの方法〔ザ・ジヤーナル・オブ・ビオケ
ミストリー58，214（1967）参照〕により、被検化
合物のジメチルスルホキシド溶液0.1ml、緩衝液
（0.1Mトリス−塩酸緩衝液；PH8.0に塩化カルシ
ウム10mMを溶解した溶液）0.1mlおよびトリプ
シン2.5μｇ／mlの緩衝液溶液0.1mlを混合した溶
液を10分間インキユベートし、これにトシルアル
ギニンメチルエステル25mMの緩衝液溶液0.2ml
を混合し、37℃で30分間反応させ、残存する基質
の量をヘステリン法により発色させ、530nmの吸
光度を測定し求めた。
結果は第１表の通りである。
(3) スロンビン阻害作用測定法
田村らの方法〔バイオキミカ・エト・バイオフ
イズイカ・アクタ484，417（1977）参照〕により、
被検化合物のジメチルスルホキシド溶液0.1ml、
緩衝液（0.1Mリン酸ナトリウム緩衝液：PH7.4）
0.1mlおよびスロンビン37.5unit／mlの緩衝液溶液
0.1mlを混合した溶液を10分間インキユベートし、
これにトシルアルギニンメチルエステル25mMの
緩衝液溶液0.2mlを混合し、37℃で30分間反応さ
せ、残存する基質の量をヘステリン法により発色
させ、530nmの吸光度を測定し求めた。
結果は第１表の通りである。
The present invention provides novel amidinophenol derivatives, more specifically, the following formula (), This invention relates to an amidinophenol derivative represented by: The present inventor synthesized various amidinophenol derivatives and searched for their pharmacological effects, and found that the amidinophenol derivative represented by the above formula () inhibits various proteolytic enzymes, such as chymotrypsin, trypsin, and thrombin. The present invention was completed based on the discovery that the present invention has an effect. Therefore, the present invention provides novel amidinophenol derivatives. The compound () of the present invention can be prepared by, for example, the following reaction: 1,2,3,4-tetrahydronaphthalene-
It is produced by reacting amidinophenol () with 1-carboxylic acid (). 1,2,3,4-tetrahydronaphthalene-1
-carboxylic acid () and amidinophenol ()
The reaction with is a normal esterification reaction, for example,
1,2,3,4-tetrahydronaphthalene-1-
It is carried out by reacting a carboxylic acid or a reactive derivative thereof with an amidinophenol or a reactive derivative thereof directly or in the presence of a condensing agent. The compound () obtained in this way can be further treated with inorganic acid salts such as hydrochloric acid, sulfuric acid, phosphoric acid and hydrobromic acid; or acetic acid, propionic acid, maleic acid, fumaric acid, It can lead to organic acid salts such as tartaric acid, citric acid, methanesulfonic acid, benzenesulfonic acid and toluenesulfonic acid. The results of testing the enzyme inhibitory effect of the thus obtained compound of the present invention () are as follows. (1) Chymotrypsin inhibitory effect According to the method of Muramatsu et al. [see The Journal of Biochemistry 62 , 408 (1967)], 0.1 ml of a dimethyl sulfoxide solution of the test compound and 0.1 ml of water were used.
A mixed solution of chymotrypsin 10 μg/ml and 0.1 ml of a buffer solution (0.1 M Tris-HCl buffer; PH 8.0) was incubated for 10 minutes, and then 0.2 ml of acetyl-L-tyrosine ethyl ester 25 mM buffer solution was incubated for 10 minutes. Mix and react at 37℃ for 30 minutes.
The amount of remaining substrate was determined by developing color using the hesterin method and measuring the absorbance at 530 nm. As comparative compounds, 4'-amidinophenyl cyclohexanecarboxylate (comparative compound 1) and tosylphenylalanine chloromethyl ketone (comparative compound 2), which is known as a chymotrypsin inhibitor, were used. The results are shown in Table 1. (2) Trypsin inhibitory effect According to the method of Muramatsu et al. [see The Journal of Biochemistry 58 , 214 (1967)], 0.1 ml of a dimethyl sulfoxide solution of the test compound and a buffer solution (0.1 M Tris-HCl buffer; A mixture of 0.1 ml of calcium chloride (10 mM solution dissolved in pH 8.0) and 0.1 ml of trypsin 2.5 μg/ml buffer solution was incubated for 10 minutes.
The mixture was mixed and reacted at 37°C for 30 minutes, and the amount of remaining substrate was determined by color development using the hesterin method and absorbance at 530 nm. The results are shown in Table 1. (3) Thrombin inhibitory effect measurement method According to the method of Tamura et al.
0.1ml of dimethyl sulfoxide solution of test compound,
Buffer (0.1M sodium phosphate buffer: PH7.4)
0.1ml and thrombin 37.5unit/ml buffer solution
Incubate the mixed solution of 0.1ml for 10 minutes,
This was mixed with 0.2 ml of a 25 mM buffer solution of tosyl arginine methyl ester, reacted at 37°C for 30 minutes, and the amount of remaining substrate was determined by developing color using the hesterin method and measuring the absorbance at 530 nm. The results are shown in Table 1.
【表】
第１表に示す結果から明らかな如く、本発明化
合物（）は優れた蛋白分解酵素阻害作用を有
し、キモトリプシン、トリプシンおよびスロンビ
ン阻害剤として有用なものである。
以下更に実施例を挙げて説明する。
実施例 １
4′−アミジノフエニル１，２，３，４−テトラ
ヒドロ−１−ナフトエート：
１，２，３，４−テトラヒドロナフタレン−１
−カルボン酸2.64ｇおよびｐ−アミジノフエノー
ル・メタンスルホン酸塩1.16ｇのピリジン10ml溶
液にジシクロヘキシルカルボジイミド3.09ｇを氷
冷下に滴下し、室温にて４時間撹拌した。反応終
了後、ジシクロヘキシルウレアを去し、母液を
濃縮乾固した。残留物にクロロホルムを加え、不
溶物を去し、溶媒を留去後、メタノールに溶か
し、エーテルを加えると、融点177〜180℃の結晶
として4′−アミジノフエニル１，２，３，４−テ
トラヒドロ−１−ナフトエート・メタンスルホン
酸塩502mg（収率46.2％）が得られた。
元素分析値：C18H18N2O2・CH3SO3Hとして
Ｃ Ｈ Ｎ Ｓ
計算値(%) 58.45 5.68 7.17 8.21
実験値(%) 58.49 5.58 7.18 8.21[Table] As is clear from the results shown in Table 1, the compound () of the present invention has an excellent protease inhibitory effect and is useful as a chymotrypsin, trypsin and thrombin inhibitor. Examples will be further described below. Example 1 4'-amidinophenyl 1,2,3,4-tetrahydro-1-naphthoate: 1,2,3,4-tetrahydronaphthalene-1
- To a solution of 2.64 g of carboxylic acid and 1.16 g of p-amidinophenol methanesulfonate in 10 ml of pyridine, 3.09 g of dicyclohexylcarbodiimide was added dropwise under ice cooling, and the mixture was stirred at room temperature for 4 hours. After the reaction was completed, dicyclohexylurea was removed and the mother liquor was concentrated to dryness. Chloroform was added to the residue to remove insoluble materials, the solvent was distilled off, the solution was dissolved in methanol, and ether was added to give 4'-amidinophenyl 1,2,3,4-tetrahydro- as crystals with a melting point of 177-180°C. 502 mg (yield 46.2%) of 1-naphthoate methanesulfonate was obtained. Elemental analysis value: C 18 H 18 N 2 O 2・CH 3 SO 3 H Calculated value (%) 58.45 5.68 7.17 8.21 Experimental value (%) 58.49 5.58 7.18 8.21
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6368579A JPS55154952A (en) | 1979-05-23 | 1979-05-23 | Amidinophenol derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6368579A JPS55154952A (en) | 1979-05-23 | 1979-05-23 | Amidinophenol derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55154952A JPS55154952A (en) | 1980-12-02 |
| JPS6340183B2 true JPS6340183B2 (en) | 1988-08-10 |
Family
ID=13236465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6368579A Granted JPS55154952A (en) | 1979-05-23 | 1979-05-23 | Amidinophenol derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55154952A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5841855A (en) * | 1981-09-07 | 1983-03-11 | Torii Yakuhin Kk | Amidine compound |
| JPS57179147A (en) * | 1981-04-28 | 1982-11-04 | Torii Yakuhin Kk | Amidine derivative |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5225740A (en) * | 1975-08-21 | 1977-02-25 | Yuichi Kaneoka | Preparation of o-acyl-amidinophenols or acid addition salts thereof |
-
1979
- 1979-05-23 JP JP6368579A patent/JPS55154952A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5225740A (en) * | 1975-08-21 | 1977-02-25 | Yuichi Kaneoka | Preparation of o-acyl-amidinophenols or acid addition salts thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55154952A (en) | 1980-12-02 |
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