JPS6256871B2 - - Google Patents
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- Publication number
- JPS6256871B2 JPS6256871B2 JP7950879A JP7950879A JPS6256871B2 JP S6256871 B2 JPS6256871 B2 JP S6256871B2 JP 7950879 A JP7950879 A JP 7950879A JP 7950879 A JP7950879 A JP 7950879A JP S6256871 B2 JPS6256871 B2 JP S6256871B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- lower alkyl
- alkyl group
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001409 amidines Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000027119 gastric acid secretion Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PBQKWXUCMGTHNU-UHFFFAOYSA-N 2-methylsulfanylpropanamide Chemical compound CSC(C)C(N)=O PBQKWXUCMGTHNU-UHFFFAOYSA-N 0.000 description 1
- GBNBIQDPFCZDCN-UHFFFAOYSA-N 3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-n'-hydroxypropanimidamide Chemical compound NC(=N)NC1=NC(CSCCC(N)=NO)=CS1 GBNBIQDPFCZDCN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- GRKUXCWELVWVMZ-UHFFFAOYSA-N amino acetate Chemical compound CC(=O)ON GRKUXCWELVWVMZ-UHFFFAOYSA-N 0.000 description 1
- SDBCCDNTZKHGBJ-UHFFFAOYSA-N amino butanoate Chemical compound CCCC(=O)ON SDBCCDNTZKHGBJ-UHFFFAOYSA-N 0.000 description 1
- KTYVHLCLTPLSGC-UHFFFAOYSA-N amino propanoate Chemical compound CCC(=O)ON KTYVHLCLTPLSGC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid 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
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は、つぎの一般式で示される新規アミジ
ン誘導体およびその酸付加塩並びにそれらの製造
法に関する。
式中の記号はつぎの意味を有している。
Ｒ：水素原子または低級アルキル基
ｍおよびｎ：夫々１〜３の整数
Ｙ：酸素原子または硫黄原子
R1：水酸基、低級アルコキシ基または低級アシ
ルオキシ基
R2：水素原子、低級アルキル基
茲に上記一般式の化合物をさらに説明すると、
一般式の説明における“低級”の語は炭素数１〜
５個を有する直鎖また分枝状の炭素鎖である。従
つて、低級アルキル基としてはメチル基、エチル
基、イソプロピル基、ブチル基などを、低級アル
コキシ基としてはメトキシ基、エトキシ基、プロ
ポキシ基などを夫々意味している。また、低級ア
シルオキシ基としては、アセトキシ基、プロピオ
ニルオキシ基、イソブチロイルオキシ基等を意味
している。
上記一般式〔〕の化合物は酸付加塩を形成
し、また互変異性体が存在するから、これらの塩
類および異性体を包含する。
本発明によつて提供される化合物〔〕は、胃
酸分泌抑制作用を有し、その作用が抗コリン作用
によらない点に特徴がある。さらに化合物〔〕
の中には、ヒスタミンH2受容体拮抗作用に基づ
いて胃酸分泌を抑制するものも存する。従来市販
の制酸剤は、そのほとんどが抗コリン作用にもと
づくものであり、また、抗コリン作用に起因する
副作用が指摘されていたところから、本発明の化
合物は新しいタイプの胃酸分泌抑制剤として有望
である。
本発明の目的化合物はShay rat 4hr法（Shsy
等、ガストロエンテロロジー第５巻43−61頁1945
年）により、10〜50mg／Kg以下の投与量で胃酸分
泌を有効に抑制することが確認されている。
本発明の目的化合物は胃酸分泌抑制を目的とし
て、１日当り、100乃至800mgを１乃至４回に分け
て投与するのが適当である。投与は遊離塩基ある
いは薬学上許容される塩の形態で行なわれる。許
容される塩としてはたとえば塩酸塩、臭化水素酸
塩、ヨウ化水素酸塩、硫酸塩、マレイン酸塩、ピ
クリン酸塩等がある。
投与は経口、非経口いずれによつても行なわ
れ、それらの投与に適した剤形は通常の方法によ
つて調製し得る。
本発明によれば、前記一般式〔〕で示される
アミジン誘導体はつぎの方法によつて製造され
る。
（式中、R′は低級アルキル基を意味する。また、
Ｒ、ｍ、ｎ、Ｙ、R1およびR2は前記の意味を有
する。）
この方法は、原料化合物〔１〕の反応対応量
の化合物〔１〕で示されるアミンを作用させる
か、原料化合物〔２〕に反応対応量の化合物
〔２〕で示されるアミンを作用させることによ
つて行なわれる。ここに使用されるアミン〔
１〕又は〔２〕は原料化合物と反応して目的化
合物〔〕を与えうるものであつて、〔１〕と
してはたとえばアンモニア、塩化アンモニウム、
メチルアミン、エチルアミン、イソプロピルアミ
ン等の低級アルキルアミン；であり、〔２〕と
してはヒドロキシルアミン、Ｏ−メチルヒドロキ
シルアミン、Ｏ−エチルヒドロキシルアミン、Ｏ
−ブチルヒドロキシルアミン等のＯ−低級アルキ
ルヒドロキシルアミン；Ｏ−アセチルヒドロキシ
ルアミン、Ｏ−プロピオニルヒドロキシルアミ
ン、Ｏ−ブチロイルヒドロキシルアミン等のＯ−
低級アシルヒドロキシルアミン等である。
この反応は通常溶媒中で行なわれ、溶媒として
はたとえばアルコール、イソプロパノール、クロ
ロホルム、エーテル、テトラヒドロフラン、ベン
ゼン等が適当である。これらの溶媒は、水を含ま
ないものが好ましい。
反応温度は特に制限はないが室温乃至加温下で
行なうのが適当である。また、反応液中の液性は
中性乃至塩基性が好ましい。
以下本発明の製造方法をさらに説明するため、
実施例を掲記する。
また、実施例中の生成物の理化学的性状を示す
記号のうち、mpは融点およびAnal.は元素分析値
を夫々意味している。
実施例 １
メチル３−（２−グアニジノチアゾール−４−
イルメチルチオ）プロピオンイミデート4.72ｇを
メチルアルコール35mlに溶解し、ヒドロキシルア
ミン塩酸塩1.2ｇをナトリウムメトキサイド0.93
ｇで処理した遊離のヒドロキシルアミンのメチル
アルコール溶液25mlを加え室温で２時間撹拌した
のち溶媒を減圧留去し残渣をクロロホルム−メチ
ルアルコール混合溶媒を展開溶媒としてカラムク
ロマトグラフイーで精製しメチルアルコール−ア
セトンにて再結晶すると３−〔（２−グアニジノチ
アゾール−４−イル）メチルチオ〕プロピオンア
ミドオキシム1.3ｇを得る。このものは、つぎの
理化学的性状を示す。
(i) mp 177〜179℃（分解）
(ii) Anal （C8H14N6OS21/4H2Oとして）
Ｃ(%) Ｈ(%) Ｎ(%)
理論値 34.46 5.24 30.14
実測値 34.78 5.23 30.06
実施例 ２
上記実施例１と同様にしてＯ−メチルヒドロキ
シルアミンを反応させ、カラムクロマトグラフイ
ーで精製した反応生成物をアセトン中でマレイン
酸で処理し、つぎの化合物4.3ｇを製造した。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel amidine derivatives represented by the following general formula, acid addition salts thereof, and methods for producing them. The symbols in the formula have the following meanings. R: hydrogen atom or lower alkyl group m and n: each integer of 1 to 3 Y: oxygen atom or sulfur atom R 1 : hydroxyl group, lower alkoxy group or lower acyloxy group R 2 : hydrogen atom, lower alkyl group In addition, the above general To further explain the compound of formula:
The word “lower” in the explanation of general formulas refers to the number of carbon atoms from 1 to
It is a straight or branched carbon chain having 5 carbon atoms. Therefore, lower alkyl groups include methyl, ethyl, isopropyl, butyl, and the like, and lower alkoxy groups include methoxy, ethoxy, propoxy, and the like. Further, the lower acyloxy group means an acetoxy group, a propionyloxy group, an isobutyroyloxy group, etc. Since the compound of the above general formula [] forms an acid addition salt and has tautomers, it includes these salts and isomers. The compound [ ] provided by the present invention is characterized in that it has a gastric acid secretion suppressing action, and its action is not based on anticholinergic action. Furthermore, the compound []
Some of them suppress gastric acid secretion based on their antagonism of histamine H2 receptors. Most of conventional commercially available antacids are based on anticholinergic effects, and side effects due to anticholinergic effects have been pointed out, so the compound of the present invention has been proposed as a new type of gastric acid secretion inhibitor. It's promising. The object compound of the present invention can be obtained using the Shay rat 4hr method (Shsy rat 4hr method).
et al., Gastroenterology, Vol. 5, pp. 43-61, 1945.
(2007), it has been confirmed that doses of 10 to 50 mg/Kg or less effectively suppress gastric acid secretion. For the purpose of suppressing gastric acid secretion, the compound of interest of the present invention is suitably administered at 100 to 800 mg per day in 1 to 4 divided doses. Administration is carried out in the form of free base or pharmaceutically acceptable salts. Acceptable salts include, for example, hydrochlorides, hydrobromides, hydroiodides, sulfates, maleates, picrates, and the like. Administration can be carried out either orally or parenterally, and dosage forms suitable for such administration can be prepared by conventional methods. According to the present invention, the amidine derivative represented by the general formula [] is produced by the following method. (In the formula, R′ means a lower alkyl group. Also,
R, m, n, Y, R 1 and R 2 have the meanings given above. ) This method involves reacting the starting compound [ 1 ] with the amine represented by the compound [ 1 ] in a reaction-corresponding amount, or reacting the raw material compound [ 2 ] with the amine represented by the compound [ 2 ] in the reaction-corresponding amount. It is carried out by. Amine used here [
1 ] or [ 2 ] can react with the raw material compound to give the target compound [ ], and [ 1 ] includes, for example, ammonia, ammonium chloride,
Lower alkylamines such as methylamine, ethylamine, and isopropylamine; and [ 2 ] includes hydroxylamine, O-methylhydroxylamine, O-ethylhydroxylamine, O-ethylhydroxylamine, and
O-lower alkylhydroxylamines such as -butylhydroxylamine; O- such as O-acetylhydroxylamine, O-propionylhydroxylamine, O-butyroylhydroxylamine, etc.
These include lower acylhydroxylamines. This reaction is usually carried out in a solvent, and examples of suitable solvents include alcohol, isopropanol, chloroform, ether, tetrahydrofuran, and benzene. These solvents preferably do not contain water. There is no particular restriction on the reaction temperature, but it is appropriate to carry out the reaction at room temperature or under heating. Further, the liquid property of the reaction solution is preferably neutral to basic. In order to further explain the manufacturing method of the present invention,
Examples are listed below. Furthermore, among the symbols indicating the physical and chemical properties of the products in the examples, mp means the melting point and Anal. means the elemental analysis value, respectively. Example 1 Methyl 3-(2-guanidinothiazole-4-
Dissolve 4.72 g of (methylthio)propionimidate in 35 ml of methyl alcohol, and dissolve 1.2 g of hydroxylamine hydrochloride in 0.93 g of sodium methoxide.
After adding 25 ml of the methyl alcohol solution of the free hydroxylamine treated in step (g) and stirring at room temperature for 2 hours, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using a chloroform-methyl alcohol mixed solvent as a developing solvent. Recrystallization from acetone yields 1.3 g of 3-[(2-guanidinothiazol-4-yl)methylthio]propionamide oxime. This material exhibits the following physical and chemical properties. (i) mp 177-179℃ (decomposition) (ii) Anal (as C 8 H 14 N 6 OS 2 1/4H 2 O) C(%) H(%) N(%) Theoretical value 34.46 5.24 30.14 Actual value 34.78 5.23 30.06 Example 2 O-methylhydroxylamine was reacted in the same manner as in Example 1 above, and the reaction product purified by column chromatography was treated with maleic acid in acetone to produce 4.3 g of the following compound. did. 【table】
Claims (1)
シルオキシ基を、 R2は水素原子、低級アルキル基を、 夫々意味する。） で示されるアミジン誘導体およびその酸付加塩。 ２ イ 一般式 で示される化合物に一般式H2N−R2で示される
アミンを反応させるか ロ 一般式 で示される化合物に一般式H2N−R1で示される
アミンを反応させることを特徴とする一般式 で示されるアミジン誘導体およびその酸付加塩
の製造法。 （式中Ｒは水素原子または低級アルキル基を、 ｍおよびｎは夫々１乃至３の整数を、 Ｙは酸素原子または硫黄原子を、 R1は水素基、低級アルコキシ基または低級
アシルオキシ基を、 R2は水素原子、低級アルキル基を、 夫々意味する。 また、R′は低級アルキル基を意味する。）[Claims] 1 (In the formula, R is a hydrogen atom or a lower alkyl group, m and n are each an integer of 1 to 3, Y is an oxygen atom or a sulfur atom, R 1 is a hydroxyl group, a lower alkoxy group, or a lower acyloxy group, R 2 means a hydrogen atom and a lower alkyl group, respectively.) Amidine derivatives and acid addition salts thereof. 2 A General formula By reacting the compound represented by the general formula H 2 N−R 2 with the amine represented by the general formula A general formula characterized by reacting a compound represented by with an amine represented by the general formula H 2 N−R 1 A method for producing amidine derivatives and acid addition salts thereof. (In the formula, R is a hydrogen atom or a lower alkyl group, m and n are each an integer of 1 to 3, Y is an oxygen atom or a sulfur atom, R 1 is a hydrogen group, a lower alkoxy group, or a lower acyloxy group, R 2 means a hydrogen atom and a lower alkyl group, respectively. Also, R' means a lower alkyl group.)
Priority Applications (27)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7950879A JPS565469A (en) | 1979-06-23 | 1979-06-23 | Novel amidine derivative and its preparation |
| AT0103080A AT374800B (en) | 1979-03-06 | 1980-02-25 | METHOD FOR PRODUCING NEW GUANIDINOTHIAZOLES AND THEIR SALTS |
| PH23689A PH16099A (en) | 1979-03-06 | 1980-02-26 | Guanidinothiazole compounds,process for preparing them and medical composition containing them |
| FI800591A FI70890C (en) | 1979-03-06 | 1980-02-27 | PROCEDURE FOR THE PREPARATION OF PHARMACOLOGICAL PROPERTIES OF GUARANIDINOTIAZOLFOERENINGAR |
| AU55975/80A AU534329B2 (en) | 1979-03-06 | 1980-02-28 | Guanioinothiazoles |
| DE19803008056 DE3008056A1 (en) | 1979-03-06 | 1980-03-03 | GUANIDINOTHIAZOL COMPOUNDS, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS |
| GR61334A GR67011B (en) | 1979-03-06 | 1980-03-03 | |
| FR8004690A FR2450827A1 (en) | 1979-03-06 | 1980-03-03 | GUANIDINOTHIAZOLE COMPOUNDS USEFUL AS INHIBITORS OF GASTRIC ACID SECRETIONS, PROCESSES FOR THEIR PREPARATION AND MEDICAL COMPOSITIONS CONTAINING SUCH COMPOUNDS |
| CH171680A CH644114A5 (en) | 1979-03-06 | 1980-03-04 | GUANIDINOTHIAZOL COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THE SAME. |
| PT70899A PT70899A (en) | 1979-03-06 | 1980-03-04 | Process for preparing useful guanidinothiazole compounds |
| CA000346986A CA1145345A (en) | 1979-03-06 | 1980-03-04 | Process for preparing guanidinothiazole compounds |
| DK093580A DK157132C (en) | 1979-03-06 | 1980-03-05 | METHOD OF ANALOGUE FOR THE PREPARATION OF GUANIDINOTHIAZOL COMPOUNDS OR ACID ADDITION SALTS |
| SE8001691A SE447253B (en) | 1979-03-06 | 1980-03-05 | NEW GUANIDINOTIAZOL SOCIETIES |
| MX8011289U MX7292E (en) | 1979-03-06 | 1980-03-05 | PROCEDURE FOR PREPARING GUANIDINOTIAZOLE COMPOUNDS |
| IT67346/80A IT1165509B (en) | 1979-03-06 | 1980-03-05 | THIAZOLIC COMPOUNDS GUANIDINO PARTICULARLY USEFUL AS INHIBITORS OF GASTRIC ACID SECRETION AND PROCEDURE FOR THEIR PREPARATION |
| ES80489222A ES8103070A1 (en) | 1979-03-06 | 1980-03-05 | Guanidinothiazole compounds, and medical compositions containing them |
| UA2891152A UA5926A1 (en) | 1979-03-06 | 1980-03-05 | Method for producing guanidine-thiasol substances |
| SU802891152A SU876056A3 (en) | 1979-03-06 | 1980-03-05 | Method of producing guanidinothiazole compounds |
| MX8011198U MX7406E (en) | 1979-03-06 | 1980-03-05 | PROCEDURE FOR PREPARING GUANIDINOTIAZOLE COMPOUNDS |
| MX808685U MX6187E (en) | 1979-03-06 | 1980-03-05 | PROCEDURE FOR PREPARING GUANIDINOTIAZOLE COMPOUNDS |
| US06/127,902 US4362736A (en) | 1979-03-06 | 1980-03-06 | Guanidinothiazole compounds, and medical compositions containing them |
| NL8001361A NL8001361A (en) | 1979-03-06 | 1980-03-06 | GUANIDINOTHIAZOLE COMPOUNDS, METHODS FOR PREPARING THE SAME, AND PHARMACEUTICAL PREPARATIONS CONTAINING THE GUANIDINOTHIAZOLE COMPOUNDS. |
| GB8007702A GB2052478B (en) | 1979-03-06 | 1980-03-06 | Guanidinothiazole compounds |
| SI8010622A SI8010622A8 (en) | 1979-03-06 | 1980-03-06 | Process for preparation of guanidine thiazole compounds |
| YU622/80A YU42966B (en) | 1979-03-06 | 1980-03-06 | Process for obtaining guanidine thiazole compounds |
| LV930547A LV5493A3 (en) | 1979-03-06 | 1993-11-30 | Saturation of guanidino-thiazole compounds |
| GEAP19942152A GEP19970667B (en) | 1979-03-06 | 1994-09-07 | Method of producing guanidinothiazole compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7950879A JPS565469A (en) | 1979-06-23 | 1979-06-23 | Novel amidine derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS565469A JPS565469A (en) | 1981-01-20 |
| JPS6256871B2 true JPS6256871B2 (en) | 1987-11-27 |
Family
ID=13691881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7950879A Granted JPS565469A (en) | 1979-03-06 | 1979-06-23 | Novel amidine derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS565469A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6061375A (en) * | 1983-09-14 | 1985-04-09 | Nissan Shatai Co Ltd | Manufacture of sandwiched noise-proof and vibration-proof structure for car |
| JPH0665620B2 (en) * | 1986-12-18 | 1994-08-24 | 日本特殊塗料株式会社 | Vibration control sheet for vehicles |
-
1979
- 1979-06-23 JP JP7950879A patent/JPS565469A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS565469A (en) | 1981-01-20 |
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