JPH06256316A - 2-n-butyl-4-imidazoledithiocarboxylic acid - Google Patents
2-n-butyl-4-imidazoledithiocarboxylic acidInfo
- Publication number
- JPH06256316A JPH06256316A JP5066053A JP6605393A JPH06256316A JP H06256316 A JPH06256316 A JP H06256316A JP 5066053 A JP5066053 A JP 5066053A JP 6605393 A JP6605393 A JP 6605393A JP H06256316 A JPH06256316 A JP H06256316A
- Authority
- JP
- Japan
- Prior art keywords
- butyl
- acid
- formula
- imidazoledithiocarboxylic
- present
- 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.)
- Pending
Links
- NBFPYLFHRNNRBH-UHFFFAOYSA-N 2-butyl-1h-imidazole-5-carbodithioic acid Chemical compound CCCCC1=NC=C(C(S)=S)N1 NBFPYLFHRNNRBH-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000000126 substance Substances 0.000 claims description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- CFYUKQRGWSQKNU-UHFFFAOYSA-N 1h-imidazole;methanedithioic acid Chemical compound SC=S.C1=CNC=N1 CFYUKQRGWSQKNU-UHFFFAOYSA-N 0.000 claims description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract description 15
- -1 alkali metal salt Chemical class 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- SLLDUURXGMDOCY-UHFFFAOYSA-N 2-butyl-1h-imidazole Chemical compound CCCCC1=NC=CN1 SLLDUURXGMDOCY-UHFFFAOYSA-N 0.000 abstract description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 4
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 3
- 239000002220 antihypertensive agent Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JLVIHQCWASNXCK-UHFFFAOYSA-N 2-butyl-5-chloro-1h-imidazole-4-carbaldehyde Chemical compound CCCCC1=NC(C=O)=C(Cl)N1 JLVIHQCWASNXCK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- RAUHREXYGRKIOJ-UHFFFAOYSA-N 1h-imidazole-5-carbodithioic acid Chemical compound SC(=S)C1=CN=CN1 RAUHREXYGRKIOJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTHGVOCFAZSNNA-UHFFFAOYSA-N 2-butyl-1h-imidazole-5-carbaldehyde Chemical compound CCCCC1=NC=C(C=O)N1 PTHGVOCFAZSNNA-UHFFFAOYSA-N 0.000 description 1
- NUVNBDKSKWPBIO-UHFFFAOYSA-N 2-butyl-1h-imidazole-5-carboxylic acid Chemical compound CCCCC1=NC=C(C(O)=O)N1 NUVNBDKSKWPBIO-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WREDNSAXDZCLCP-UHFFFAOYSA-N methanedithioic acid Chemical compound SC=S WREDNSAXDZCLCP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、血圧降下剤などの医薬
品等の中間体として有用である新規な２−ｎ−ブチル−
４−イミダゾールジチオカルボン酸に関するものであ
る。また本発明化合物は、同じく医薬品等の中間体とし
て有用である２−ｎ−ブチル−４−クロロ−５−フォル
ミルイミダゾールを製造する際の原料物質として有用な
ものである。The present invention relates to a novel 2-n-butyl-containing compound useful as an intermediate for pharmaceuticals such as antihypertensive agents.
It relates to 4-imidazole dithiocarboxylic acid. Further, the compound of the present invention is also useful as a raw material for producing 2-n-butyl-4-chloro-5-formylimidazole which is also useful as an intermediate for pharmaceuticals and the like.
【０００２】[0002]
【従来の技術】特公昭６０−２９７０７号公報には、イ
ミダゾール化合物と二硫化炭素と水酸化アルカリの三者
を溶剤の存在下加熱反応させることにより、２位にメチ
ル基、エチル基、ウンデシルル基、ヘプタデシルル基及
びフェニル基を有する４−イミダゾールジチオカルボン
酸化合物並びにこれらの４−イミダゾールジチオカルボ
ン酸化合物を用いた銀金属の防錆方法が記載されている
が、医薬品等の中間体として有用であり、かつ新規な本
発明化合物については何ら開示されていない。In Japanese Patent Publication No. 60-29707, a imidazole compound, carbon disulfide and an alkali hydroxide are heated and reacted in the presence of a solvent to cause a methyl group, an ethyl group and an undecyl group at the 2-position. , 4-imidazole dithiocarboxylic acid compound having a heptadecyl group and a phenyl group and a method for preventing rusting of silver metal using these 4-imidazole dithiocarboxylic acid compounds are described, but they are useful as intermediates for pharmaceuticals and the like. Nothing is disclosed about the novel compound of the present invention.
【０００３】本発明の２−ｎ−ブチル−４−イミダゾー
ルジチオカルボン酸は、１当量以上の酸と共に水の存在
下煮沸するか、あるいは水の存在下鉱酸と反応させチオ
フォルミルイミダゾール化合物となし、次いでイミダゾ
ールジチオカルボン酸に対して等モル以上の金属塩を反
応させることにより２−ｎ−ブチル−４−フォルミルイ
ミダゾールが得られ、さらに塩素化剤を反応させること
により同じく医薬品等の中間体として有用な２−ｎ−ブ
チル−４−クロロ−５−フォルミルイミダゾール化合物
を得ることができる。The 2-n-butyl-4-imidazoledithiocarboxylic acid of the present invention is boiled in the presence of water with 1 equivalent or more of an acid, or is reacted with a mineral acid in the presence of water to give a thioformylimidazole compound. None, and then by reacting an equimolar or more metal salt with imidazole dithiocarboxylic acid, 2-n-butyl-4-formylimidazole can be obtained. A 2-n-butyl-4-chloro-5-formylimidazole compound useful as a body can be obtained.
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は、血圧
降下剤などの医薬品等の中間体として注目されている２
−ｎ−ブチル−４−クロロ−５−フォルミルイミダゾー
ルを安価に且つ大量に製造するための原料として有用な
２−ｎ−ブチル−４−イミダゾールジチオカルボン酸を
提供することである。The object of the present invention has attracted attention as an intermediate for pharmaceutical products such as antihypertensive agents 2
It is an object of the present invention to provide 2-n-butyl-4-imidazoledithiocarboxylic acid useful as a raw material for inexpensively producing a large amount of -n-butyl-4-chloro-5-formylimidazole.
【０００５】[0005]
【課題を解決するための手段】本発明者等は、このよう
な事情に鑑み種々の試験を重ねた結果、２−ｎ−ブチル
−４−クロロ−５−フォルミルイミダゾールを安価に且
つ大量に製造するための原料として、化２で示される２
−ブチル−４−イミダゾールジチオカルボン酸が適して
いることを知見し、本発明を完遂するに至った。The present inventors have conducted various tests in view of such circumstances, and as a result, 2-n-butyl-4-chloro-5-formylimidazole was produced inexpensively and in a large amount. As a raw material for manufacturing,
-Butyl-4-imidazole dithiocarboxylic acid was found to be suitable, and the present invention was completed.
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】即ち、２−ｎ−ブチルイミダゾールに当量
モル以上の二硫化炭素及び当量モル以上の水酸化アルカ
リを溶剤の存在下加え、加熱することにより２−ｎ−ブ
チル−４−イミダゾールジチオカルボン酸アルカリ金属
塩が得られる。次いで、酸を添加して２−ｎ−ブチル−
４−イミダゾールジチオカルボン酸アルカリ金属塩を酸
性化処理することにより、本発明の２−ｎ−ブチル−４
−イミダゾールジチオカルボン酸が得られる。これを反
応式で表せば化３に示されるとおりである。That is, 2-n-butyl-4-imidazole dithiocarboxylic acid is added to 2-n-butylimidazole by adding an equivalent mole or more of carbon disulfide and an equivalent mole or more of alkali hydroxide in the presence of a solvent and heating the mixture. An alkali metal salt is obtained. Then add acid to add 2-n-butyl-
2-n-butyl-4 of the present invention is obtained by acidifying 4-imidazole dithiocarboxylic acid alkali metal salt.
-Imidazole dithiocarboxylic acid is obtained. This can be represented by the reaction formula as shown in Chemical formula 3.
【０００８】[0008]
【化３】 [Chemical 3]
【０００９】本発明化合物を製造するに当たって、２−
ｎ−ブチルイミダゾール、二硫化炭素及び水酸化アルカ
リを溶剤に混合し、室温ないし１５０℃の温度範囲、好
ましくは８０〜８５℃の温度に加熱して反応させる。そ
の際の加熱反応時間は１．５〜３時間の範囲が好適であ
る。In producing the compound of the present invention, 2-
n-Butylimidazole, carbon disulfide and alkali hydroxide are mixed in a solvent and heated to a temperature range of room temperature to 150 ° C., preferably 80 to 85 ° C. to react. The heating reaction time at that time is preferably in the range of 1.5 to 3 hours.
【００１０】本発明化合物を製造するに当たって用いら
れる代表的な溶剤としては、ジメチルスルホキシド、
水、メタノール、ブタノール、エチレングリコール、ピ
リジン、ピコリン類、トリエチルアミン、アセトニトリ
ル、アセトンメチルセロソルブ、ＤＭＦ等であり、特に
ジメチルスルホキシドが好適である。As a typical solvent used for producing the compound of the present invention, dimethyl sulfoxide,
Water, methanol, butanol, ethylene glycol, pyridine, picoline, triethylamine, acetonitrile, acetone methyl cellosolve, DMF and the like are preferable, and dimethyl sulfoxide is particularly preferable.
【００１１】本発明化合物の製造に当たって、２−ｎ−
ブチル−４−イミダゾールジチオカルボン酸アルカリ金
属塩を酸性化処理するために用いられる酸の代表的なも
のとしては、塩酸、硫酸、硝酸、燐酸及び酢酸等であ
る。In producing the compound of the present invention, 2-n-
Typical acids used for acidifying the butyl-4-imidazoledithiocarboxylic acid alkali metal salt are hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid and the like.
【００１２】本発明の新規な２−ｎ−ブチル−４−イミ
ダゾールジチオカルボン酸の物性は、次に示すとおりで
ある。 赤レンガ色中性結晶。融点：１３１．４〜１３５℃ ＤＭＳＯ、ＤＭＦに易溶。メタノール、熱水に可溶。ア
セトンに難溶。 ＴＬＣ（シリカＧ／エタノール、Ｉ2 ）：Ｒｆ０．５０
〜０．７５ ＩＲ(KBr):ν3240( 7),2940( 5),1605( 9),1530(15),14
60(36),1300(45),1250(30),1210( 7),1110(20),1045(
1),1020( 5), 980(11),845(28), 825(24), 750(46) cm
-1（透過率） ＮＭＲ(DMSO-d6) ：δ7.70(s,1H,イミダゾール環の５位
プロトン),2.88(t,J=7.2Hz,2H,ブチル基),1.8 〜1.1(m,
4H, ブチル基),0.89(t,J=6.8Hz,3H,ブチル基) ＭＳ：m/e 200( M+ ）,167(M+ -SH),124(M+ -CSSH)The physical properties of the novel 2-n-butyl-4-imidazoledithiocarboxylic acid of the present invention are as follows. Red brick neutral crystals. Melting point: 131.4 to 135 ° C. Soluble in DMSO and DMF. Soluble in methanol and hot water. Hardly soluble in acetone. TLC (silica G / ethanol, I 2 ): Rf 0.50
~ 0.75 IR (KBr): ν3240 (7), 2940 (5), 1605 (9), 1530 (15), 14
60 (36), 1300 (45), 1250 (30), 1210 (7), 1110 (20), 1045 (
1), 1020 (5), 980 (11), 845 (28), 825 (24), 750 (46) cm
-1 (Transmittance) NMR (DMSO-d 6 ): δ7.70 (s, 1H, 5th position proton of imidazole ring), 2.88 (t, J = 7.2Hz, 2H, butyl group), 1.8 to 1.1 (m ,
4H, butyl group), 0.89 (t, J = 6.8Hz, 3H, butyl group) MS: m / e 200 (M + ), 167 (M + -SH), 124 (M + -CSSH)
【００１３】[0013]
【実施例】以下、実施例によって、本発明を具体的に説
明する。 （実施例１）２−ｎ−ブチルイミダゾール１５０ｇ
（１．２モル）をジメチルスルホキシド５０４ｇに溶か
し、この溶液に水酸化ナトリウム９７．６ｇ（２．４モ
ル）を加えて溶解させ、さらに二硫化炭素１１０ｇ
（１．４５モル）を滴下したのち、８０℃ないし８５℃
の温度において２．５時間加熱攪拌を行った。得られた
反応混合物を濃縮し、これに水１２００ｍｌを加えて濃
縮物を溶解させ、この水溶液に７５％燐酸３５３ｇ
（２．７モル）を加えて中和し、析出してくる結晶を分
取し、水洗、乾燥して本発明の２−ｎ−ブチル−４−イ
ミダゾールカルボン酸１６０ｇ（収率６６％）を得た。EXAMPLES The present invention will be specifically described below with reference to examples. (Example 1) 150 g of 2-n-butylimidazole
(1.2 mol) was dissolved in 504 g of dimethylsulfoxide, 97.6 g (2.4 mol) of sodium hydroxide was added to and dissolved in this solution, and 110 g of carbon disulfide was further added.
(1.45 mol) was added dropwise, then 80 ° C to 85 ° C
The mixture was heated and stirred at the temperature of 2.5 hours. The obtained reaction mixture was concentrated, 1200 ml of water was added thereto to dissolve the concentrate, and 353 g of 75% phosphoric acid was added to this aqueous solution.
(2.7 mol) was added for neutralization, and the precipitated crystals were separated, washed with water and dried to obtain 160 g of 2-n-butyl-4-imidazolecarboxylic acid of the present invention (yield 66%). Obtained.
【００１４】[0014]
【発明の効果】本発明化合物は、医薬品の中間体として
有用な２−ｎ−ブチル−４−クロロ−５−フォルミルイ
ミダゾールを製造するための比較的安価な原料として使
用できるうえに、製造工程における処理も容易であるの
で、工業的規模の実施に適している。INDUSTRIAL APPLICABILITY The compound of the present invention can be used as a relatively inexpensive raw material for producing 2-n-butyl-4-chloro-5-formylimidazole which is useful as an intermediate for pharmaceuticals, and the production process It is also suitable for industrial scale implementation as it is easy to process.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 村井 孝行 香川県仲多度郡多度津町大字東白方498番 地 (72)発明者 狩野 直喜 香川県丸亀市土器町東７丁目164番地 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Takayuki Murai 498 East Higashishikata, Tadotsu-cho, Nakatado-gun, Kagawa (72) Inventor Naoki Kano 7164, Higashi-cho, Marugame, Kagawa
Claims (1)
イミダゾールジチオカルボン酸。 【化１】 1. 2-n-butyl-4-represented by Chemical Formula 1
Imidazole dithiocarboxylic acid. [Chemical 1]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5066053A JPH06256316A (en) | 1993-03-01 | 1993-03-01 | 2-n-butyl-4-imidazoledithiocarboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5066053A JPH06256316A (en) | 1993-03-01 | 1993-03-01 | 2-n-butyl-4-imidazoledithiocarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06256316A true JPH06256316A (en) | 1994-09-13 |
Family
ID=13304753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5066053A Pending JPH06256316A (en) | 1993-03-01 | 1993-03-01 | 2-n-butyl-4-imidazoledithiocarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06256316A (en) |
-
1993
- 1993-03-01 JP JP5066053A patent/JPH06256316A/en active Pending
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