JPS5811948B2 - Method for producing heterocyclic compounds - Google Patents

Method for producing heterocyclic compounds

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Publication number
JPS5811948B2
JPS5811948B2 JP52160989A JP16098977A JPS5811948B2 JP S5811948 B2 JPS5811948 B2 JP S5811948B2 JP 52160989 A JP52160989 A JP 52160989A JP 16098977 A JP16098977 A JP 16098977A JP S5811948 B2 JPS5811948 B2 JP S5811948B2
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JP
Japan
Prior art keywords
formula
heterocyclic compounds
compound
imidazole
producing heterocyclic
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
Application number
JP52160989A
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Japanese (ja)
Other versions
JPS53119869A (en
Inventor
グラハム・ジヨン・ダラント
シヤロン・ロビン・ガネリン
ジヨン・コリン・エメツト
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Smith Kline and French Laboratories Ltd
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Smith Kline and French Laboratories Ltd
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26240626&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JPS5811948(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from GB635271A external-priority patent/GB1338169A/en
Application filed by Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of JPS53119869A publication Critical patent/JPS53119869A/en
Publication of JPS5811948B2 publication Critical patent/JPS5811948B2/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms
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    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/46—Sulfur atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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Description

【発明の詳細な説明】 本発明はイミダゾール誘導体の製造法、更に詳しくは、
Ｈ−１受容体以外のヒスタミン受容体に作用する抗ヒス
タミン剤として有用な化合物製造における中間体として
有用なイミダゾール誘導体の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing imidazole derivatives, more specifically,
The present invention relates to a method for producing imidazole derivatives useful as intermediates in the production of compounds useful as antihistamine agents that act on histamine receptors other than H-1 receptors.

従来、生理学的活性物質はその活性を現わす過程におい
て、動物体内中、受容体として知られるある種の特殊な
役割を果たす部位と結合するものと仮定されている。Conventionally, it has been assumed that in the process of exerting its activity, physiologically active substances bind to sites in the animal body that play certain special roles, known as receptors.

ヒスタミンは動物体内において上記のごとき機作に従っ
て作用を発揮すると考えられている物質であって、その
作用には複数の種類があるところから、ヒスタミン受容
体にも複数の種類があるものと信じられている。Histamine is a substance that is thought to exert its effects in the animal body according to the mechanism described above, and since there are multiple types of its effects, it is believed that there are multiple types of histamine receptors as well. ing.

通常、抗ヒスタミン剤（たとえばメピラミン）と呼ばれ
る薬剤によって阻止されるヒスタミン作用の類型は、ア
ツシおよびシールドによりＨ−１と命名された受容体（
ブリティッシュ・ジャーナル・オブ・ファーマクロジー
２）巻４２７頁（１９６６年）参照）が関与するものと
考えられる。The type of histamine action that is usually blocked by drugs called antihistamines (e.g., mepyramine) is caused by a receptor designated H-1 by Atsushi and Shields (
(see British Journal of Pharmacology, Vol. 2), p. 427 (1966)).

本発明の目的は、Ｈ−１受容体以外のヒスタミン受容体
に作用し、前記抗ヒスタミン剤によって抑制されないあ
る種のヒスタミン作用を抑制し、また、ガストリンの有
するある種の作用に対する抑制剤として有用な化合物製
造における中間体として有用なイミダゾール誘導体の製
造法を提供することである。The object of the present invention is to provide a compound that acts on histamine receptors other than H-1 receptors, suppresses certain histamine effects that are not suppressed by the above-mentioned antihistamines, and is also useful as an inhibitor for certain effects of gastrin. An object of the present invention is to provide a method for producing imidazole derivatives useful as intermediates in production.

すなわち、本発明によれば、式 〔式中、Ｑはハロゲンを表わす〕 で示される化合物をアルカリ金属アジドと反応させ、つ
いで、得られた生成物を還元して式で示される目的とす
るイミダゾール誘導体が得られる。That is, according to the present invention, a compound represented by the formula [wherein Q represents a halogen] is reacted with an alkali metal azide, and the resulting product is then reduced to obtain the desired imidazole represented by the formula. A derivative is obtained.

用いるハロ出発物質は、たとえば、ハロアルキルイミダ
ゾール化合物とジオール体のナトリウム塩を反応させて
対応するアルコール体を得、これをチオニルハライドと
反応させることにより製せられる。The halo starting material used is produced, for example, by reacting a haloalkylimidazole compound with a sodium salt of a diol to obtain the corresponding alcohol, and reacting this with thionyl halide.

反応生成物の還元は、たとえば、二酸化白金触媒上水素
化のごとき方法で行なえる。Reduction of the reaction product can be carried out, for example, by hydrogenation over a platinum dioxide catalyst.

化合物〔■〕は酸付加塩の形で存在し得る。Compound [■] may exist in the form of an acid addition salt.

またこの酸付加塩を適当な塩基、たとえば、ナトリウム
エトキシドのごときアルカリ金属アルコキシドまたは炭
酸カリウムのごとき無機塩基と処理することによって式
〔■〕の遊離塩基を得ることができる。Alternatively, the free base of formula [■] can be obtained by treating this acid addition salt with a suitable base, for example an alkali metal alkoxide such as sodium ethoxide or an inorganic base such as potassium carbonate.

前記のごとく、化合物〔■〕は動物体内においてメピラ
ミンのごとき抗ヒスタミン剤によって阻止されないある
種のヒスタミンの働きに対する拮抗剤として有用な化合
物の製造中間体として用いられる。As mentioned above, the compound [■] is used as an intermediate in the production of compounds useful as antagonists to the action of certain histamines that are not inhibited by antihistamines such as mepyramine in the animal body.

たとえば、式〔■〕の化合物を、式 Ｒ−Ｎ＝Ｃ＝Ｓ 〔式中、Ｒは低級アルキルを表わす〕 で示される化合物と反応させることによりメピラミンの
ごとき抗ヒスタミン剤によって阻止されないある種のヒ
スタミンの働きに対する拮抗剤として有用な化合物が得
られる。For example, by reacting a compound of the formula [■] with a compound of the formula R-N=C=S, where R represents lower alkyl, certain histamines that are not inhibited by antihistamines such as mepyramine can be inhibited. Compounds are obtained that are useful as antagonists to the action.

つぎに実施例を挙げて本発明を更に詳しく説明するが、
これらに限定されるものではない。Next, the present invention will be explained in more detail with reference to Examples.
It is not limited to these.

実施例 ４−（２−クロロエトキシメチル）イミダゾール・塩酸
塩１４．７ｇおよびナトリウムアジド９．８ｇの乾燥ジ
メチルホルムアミド１０３ｍ１懸濁液を攪拌しながら９
５℃で５時間保持し、室温で一夜放置する。Example 4 - A suspension of 14.7 g of (2-chloroethoxymethyl)imidazole hydrochloride and 9.8 g of sodium azide in 103 ml of dry dimethylformamide was prepared with stirring.
Hold at 5°C for 5 hours and leave at room temperature overnight.

これを水で希釈し、濾過して濾液を濃縮し、得られた残
渣を乾燥アルミナカラム上、エタノールを使用するクロ
マトグラフィーにより精製する。It is diluted with water, filtered, the filtrate is concentrated and the resulting residue is purified by chromatography on a dry alumina column using ethanol.

これを水３ｍｌ中炭酸カリウム６．５ｇで塩基性にし、
残渣の無水物をイソプロピルアルコール５０ｍ１で３回
抽出する。This was made basic with 6.5 g of potassium carbonate in 3 ml of water,
The anhydrous residue is extracted three times with 50 ml of isopropyl alcohol.

抽出物を濃縮して４−（２−アジドエトキシメチル）イ
ミダゾール７．２ｇを得る。The extract is concentrated to obtain 7.2 g of 4-(2-azidoethoxymethyl)imidazole.

アジド化合物７．２ｇをイソプロピルアルコール中、酸
化白金触媒３．０ｇ上で水素化し、目的とする４−（２
−アミノエトキシメチル）イミダゾール６．４８ｇを得
る。7.2 g of the azide compound was hydrogenated in isopropyl alcohol over 3.0 g of platinum oxide catalyst to obtain the desired 4-(2
6.48 g of -aminoethoxymethyl)imidazole are obtained.

−ピコリン酸・一塩酸塩の融点：１３９〜１４０℃にト
ロメタン）。-Melting point of picolinic acid monohydrochloride: 139-140°C (tromethane).

元素分析 Ｃｌ２Ｈ１５ＣｌＮ６Ｏ８として、計算値
Ｃ，３５，４％；Ｈ，３，７％；Ｎ、２０．７％；Ｃｌ
、８．７％； 実測値 Ｃ，３５，４％；Ｈ，３，８％；Ｎ、２０．５
％；Ｃｌ、８．８％； ４−（２−アミノエトキシメチル）イミダゾールをイソ
プロピルアルコール中、メチルイソチオシアネートと反
応させると、Ｈ−１受容体以外のヒスタミン受容体に作
用する抗ヒスタミン剤として有用なＮ−メチル−Ｎ´−
〔２−（４−イミダゾリルメトキシ）エチル〕チオウレ
アが得られる。Elemental analysis Calculated value as Cl2H15ClN6O8
C, 35.4%; H, 3.7%; N, 20.7%; Cl
, 8.7%; Actual value C, 35.4%; H, 3.8%; N, 20.5
%; Cl, 8.8%; When 4-(2-aminoethoxymethyl)imidazole is reacted with methyl isothiocyanate in isopropyl alcohol, N -Methyl-N'-
[2-(4-imidazolylmethoxy)ethyl]thiourea is obtained.

融点＝９６〜９８℃。Melting point = 96-98°C.

Claims (1)

【特許請求の範囲】 １式 〔式中、Ｑはハロゲンを表わす〕 で示される化合物をアルカリ金属アジドと反応させ、つ
いで、得られた生成物を還元することを特徴とする式 で示されるイミダゾール誘導体の製造法。[Claims] An imidazole represented by the formula 1, characterized in that the compound represented by the formula 1 [in the formula, Q represents a halogen] is reacted with an alkali metal azide, and the resulting product is then reduced. Method for producing derivatives.
JP52160989A 1971-03-09 1977-12-22 Method for producing heterocyclic compounds Expired JPS5811948B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB635271A GB1338169A (en) 1971-03-09 1971-03-09 Ureas thioureas and guanidines
GB3433471 1971-07-22

Publications (2)

Publication Number Publication Date
JPS53119869A JPS53119869A (en) 1978-10-19
JPS5811948B2 true JPS5811948B2 (en) 1983-03-05

Family

ID=26240626

Family Applications (5)

Application Number Title Priority Date Filing Date
JP2437172A Pending JPS5324422B1 (en) 1971-03-09 1972-03-09
JP16098777A Granted JPS53119867A (en) 1971-03-09 1977-12-22 Process for preparing heterocyclic compounds
JP52160989A Expired JPS5811948B2 (en) 1971-03-09 1977-12-22 Method for producing heterocyclic compounds
JP16098877A Granted JPS53119868A (en) 1971-03-09 1977-12-22 Process for preparing heterocyclic compounds
JP11573678A Pending JPS5459275A (en) 1971-03-09 1978-09-19 Production of heterocyclic compound

Family Applications Before (2)

Application Number Title Priority Date Filing Date
JP2437172A Pending JPS5324422B1 (en) 1971-03-09 1972-03-09
JP16098777A Granted JPS53119867A (en) 1971-03-09 1977-12-22 Process for preparing heterocyclic compounds

Family Applications After (2)

Application Number Title Priority Date Filing Date
JP16098877A Granted JPS53119868A (en) 1971-03-09 1977-12-22 Process for preparing heterocyclic compounds
JP11573678A Pending JPS5459275A (en) 1971-03-09 1978-09-19 Production of heterocyclic compound

Country Status (21)

Country Link
JP (5) JPS5324422B1 (en)
AR (2) AR197080A1 (en)
BE (1) BE779775A (en)
CY (1) CY856A (en)
DK (1) DK139870B (en)
EG (1) EG10876A (en)
ES (1) ES400587A1 (en)
FI (1) FI60393C (en)
HK (1) HK55176A (en)
HU (1) HU164509B (en)
IE (1) IE36050B1 (en)
IL (1) IL38821A (en)
IT (1) IT1041101B (en)
KE (1) KE2625A (en)
MY (1) MY7600228A (en)
NO (1) NO133196C (en)
PH (2) PH12207A (en)
SE (3) SE402288B (en)
SG (1) SG28576G (en)
SU (1) SU460628A3 (en)
ZM (1) ZM3672A1 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1398426A (en) * 1972-09-05 1975-06-18 Smith Kline French Lab Heterocyclic substituted guanidines
GB1397436A (en) * 1972-09-05 1975-06-11 Smith Kline French Lab Heterocyclic n-cyanoguinidines
US4083988A (en) * 1972-09-05 1978-04-11 Smith Kline & French Laboratories Limited Pharmacologically active compounds
US4000296A (en) * 1972-09-05 1976-12-28 Smith Kline & French Laboratories Limited Imidazole alkylguanidine compounds
US4129657A (en) 1975-03-21 1978-12-12 Smith, Kline & French Laboratories Limited Imidazole guanidines and use as inhibitors of histamine activity
IL56265A (en) * 1977-12-28 1982-08-31 Om Lab Sa Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor
JPH07107054B2 (en) * 1987-05-20 1995-11-15 株式会社日本触媒 Process for producing 4-methyl-5-[(2-aminoethyl) thiomethyl] imidazole dihydrochloride
JP2933739B2 (en) * 1990-04-09 1999-08-16 明治製菓株式会社 Thiazole or imidazole derivatives and anti-ulcer agents

Also Published As

Publication number Publication date
MY7600228A (en) 1976-12-31
PH12247A (en) 1978-12-12
SU460628A3 (en) 1975-02-15
IL38821A (en) 1975-05-22
SE410103B (en) 1979-09-24
JPS53119868A (en) 1978-10-19
KE2625A (en) 1976-05-28
CY856A (en) 1976-09-10
HU164509B (en) 1974-02-28
AR197080A1 (en) 1974-03-15
JPS5324422B1 (en) 1978-07-20
FI60393C (en) 1982-01-11
DK139870C (en) 1979-10-08
IE36050B1 (en) 1976-08-04
IL38821A0 (en) 1972-10-29
EG10876A (en) 1976-07-31
SE7610842L (en) 1976-09-30
HK55176A (en) 1976-09-17
JPS53119867A (en) 1978-10-19
JPS5459275A (en) 1979-05-12
ES400587A1 (en) 1975-07-16
DK139870B (en) 1979-05-07
NO133196B (en) 1975-12-15
NO133196C (en) 1976-03-24
SE7412680L (en) 1974-10-09
SG28576G (en) 1987-04-03
IE36050L (en) 1972-09-09
JPS53119869A (en) 1978-10-19
JPS5732063B2 (en) 1982-07-08
JPS5742068B2 (en) 1982-09-07
PH12207A (en) 1978-11-29
SE402288B (en) 1978-06-26
AR197093A1 (en) 1974-03-15
BE779775A (en) 1972-08-24
ZM3672A1 (en) 1972-10-23
IT1041101B (en) 1980-01-10
SE430689B (en) 1983-12-05
FI60393B (en) 1981-09-30

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