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JPS6056143B2 - アミジン誘導体ならびにその製造法 - Google Patents

アミジン誘導体ならびにその製造法

Info

Publication number
JPS6056143B2
JPS6056143B2 JP54098906A JP9890679A JPS6056143B2 JP S6056143 B2 JPS6056143 B2 JP S6056143B2 JP 54098906 A JP54098906 A JP 54098906A JP 9890679 A JP9890679 A JP 9890679A JP S6056143 B2 JPS6056143 B2 JP S6056143B2
Authority
JP
Japan
Prior art keywords
formula
guanidinothiazol
ylmethylthio
propionamidine
sulfamoyl
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
JP54098906A
Other languages
English (en)
Other versions
JPS5622770A (en
Inventor
康文 平田
勲 柳沢
吉雄 石井
紳一 塚本
徳樹 伊藤
八州男 磯村
正明 竹田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Yamanouchi Pharmaceutical Co Ltd
Original Assignee
Yamanouchi Pharmaceutical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=14232166&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JPS6056143(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to JP54098906A priority Critical patent/JPS6056143B2/ja
Application filed by Yamanouchi Pharmaceutical Co Ltd filed Critical Yamanouchi Pharmaceutical Co Ltd
Priority to GB7943945A priority patent/GB2055800B/en
Priority to DE2951675A priority patent/DE2951675C2/de
Priority to PH23454A priority patent/PH15657A/en
Priority to SE7910568A priority patent/SE444317B/sv
Priority to CH11362/79A priority patent/CH648027A5/de
Priority to US06/107,629 priority patent/US4283408A/en
Priority to NLAANVRAGE7909321,A priority patent/NL180420C/xx
Priority to CA000342699A priority patent/CA1134836A/en
Priority to ES487381A priority patent/ES8100281A1/es
Priority to FR797931938A priority patent/FR2462431B1/fr
Priority to IT69498/79A priority patent/IT1119641B/it
Priority to AT0103080A priority patent/AT374800B/de
Priority to FI800591A priority patent/FI70890C/fi
Priority to AU55975/80A priority patent/AU534329B2/en
Priority to GR61334A priority patent/GR67011B/el
Priority to PT70899A priority patent/PT70899A/pt
Priority to SU802891152A priority patent/SU876056A3/ru
Priority to MX8011198U priority patent/MX7406E/es
Priority to UA2891152A priority patent/UA5926A1/uk
Priority to MX8011289U priority patent/MX7292E/es
Priority to DK093580A priority patent/DK157132C/da
Priority to YU622/80A priority patent/YU42966B/xx
Priority to SI8010622A priority patent/SI8010622A8/sl
Publication of JPS5622770A publication Critical patent/JPS5622770A/ja
Publication of JPS6056143B2 publication Critical patent/JPS6056143B2/ja
Priority to CA000521982A priority patent/CA1222763B/en
Priority to NL930038C priority patent/NL930038I2/nl
Priority to LV930547A priority patent/LV5493A3/xx
Priority to GEAP19942152A priority patent/GEP19970667B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • 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
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Description

【発明の詳細な説明】 本発明は、つぎに式〔Ｉ〕で示される新規Ｎ−スルフア
モイルー ３−（２−グアニジノチアゾールー４−イル
メチルチオ）プロピオンアミジンまたはその酸付加塩並
びにそれらの製造法に関す”る。
上記式〔１〕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〔１〕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〔１〕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である。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
Ｓｈａｙｒａｔ４ｈｒ法（Ｓｈａｙ等、ガストロエンテ
ロロジー第５巻４３−６１頁１９４５年）により、１０
〜５０ｍ９／Ｋｇ以下すなわち、０．３−３１ａ９／Ｋ
９程度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、１０乃至２００ＷＬｇ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、フマール酸塩、マ
レイン酸塩、コハク酸塩、酒石酸塩、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〔１〕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Ｄｉ！！ｉする。
）この方法は、原料化合物〔■１〕に反応対応量乃至過
剰量のアンモニアまたはその塩（たとえば塩化アンモニ
ウムなど）を作用させるか、原料化合物〔■２〕に反応
対応量乃至過剰量のスルフアクミド〔■２〕を作用させ
ることによつて行なわれる。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メタノール、エタノール
、イソプロパノールなどのアルコール類、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。
なお、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、Ａｎａｌは元素分析値、ＮＭＲは核磁
気共鳴スペクトルおよびＭａｓｓｌは質量スペクトルを
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ー４−イルメチ
ルチオ）プロピオンイミデート４．０９ｆをメチルアル
コール３０ｍ１に溶解し、スルファミド２．８８のメチ
ルアルコール溶液１５ｍ１を還流下、滴下する。
約３時間還流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（２０：１→１０：１
）を展開溶媒としてシリカゲルカラムクロマトグラフィ
ーで精製しＮ−スルファモイルー３−（２−グアニジノ
チアゾールー４−イルメチルチオ）プロピオンアミジン
３．２６ｆを得る。このものは、つぎの理化学的性状を
示す。Ｉｍｐｌ６３〜１６４℃ＪＡｎａｌ．（Ｃ８Ｈｌ
５Ｎ７Ｏ２ｓ３として）ＪｉＮＭＲ（ＤＭＳＯ−Ｄ６）
δ ２．５０（２Ｈ，ｍ，−ＳＣＨ２Ｃ旦２−） ２．
６５（２Ｈ，ｍ，−ＳＣＨ２ＣＨ２−）６．４５（１Ｈ
，Ｓ，（］）ＩｖＭａｓｓ．（ＦＤ法）ｍ／Ｅ３３８ 実施例２ （１）スルファミド７．７ｙをメチルアルコール３０ｍ
１に加熱溶解し、３０℃に冷却する。
この溶液にメーチル３−（２−グアニジノチアゾールー
４−イルメチルチオ）プロピオンイミデート１０′を３
等分し、３回に分けて、攪拌下２０〜３０Ｃで加える。
（第２回目及び第３回目はそれぞれ第１回目の４時間後
および８時間後に加える。）反応混合物をさらに２日間
、２０〜３０℃で攪拌した後、生成した結晶を淵取し、
冷メチルアルコールで洗浄し、デシケ−ター中で乾燥す
れば７．４ｙｆ）Ｎ−スルファモイルー３−（２−グア
ニジノチアゾールー４−イルメチルチオ）プロピオンア
ミジンが得られる。
生成物の一部をジメチルホルムアミドー水から再結晶し
、さらに等モル量の酢酸水に溶解したのち、等モル量の
稀水酸化ナトリウム水溶液を加えることにより析出させ
た結晶はつぎの理化学的性状を示す。
Ｉｍｐｌ６４〜１６５出Ｃ ｉＡｒ］ａ１（Ｃ８Ｈｌ５Ｎ７Ｏ２ｓ３として）（２）
（１）で得られた化合物５ｙを１Ｎ塩酸１４．８ｍ１
，水１０ｒ１Ｌ１の溶液に溶かし氷冷し、析出してくる
結晶を枦取し、デシケ−ター中で乾燥すれば４．５ｙの
塩酸塩が得られる。
Ｉｍｐｌ屹〜１９４℃

Claims (1)

  1. 【特許請求の範囲】 １ 式 ▲数式、化学式、表等があります▼ で示されるＮ−スルフアモイル−３−（２−グアニジノ
    チアゾール−４−イルメチルチオ）プロピオンアミジン
    またはその酸付加塩。 ２ 一般式 ▲数式、化学式、表等があります▼ で示される化合物にアンモニアまたはその塩を反応させ
    ることを特徴とする式▲数式、化学式、表等があります
    ▼ で示されるＮ−スルフアモイル−３−（２−グアニジノ
    チアゾール−４−イルメチルチオ）プロピオンアミジン
    またはその酸付加塩の製造法。 ３ 一般式 ▲数式、化学式、表等があります▼ で示される化合物にスルファミドを反応させることを特
    徴とする式▲数式、化学式、表等があります▼ で示されるＮ−スルフアモイル−３−（２−グアニジノ
    チアゾール−４−イルメチルチオ）プロピオンアミジン
    またはその酸付加塩の製造法。
JP54098906A 1979-03-06 1979-08-02 アミジン誘導体ならびにその製造法 Expired JPS6056143B2 (ja)

Priority Applications (28)

Application Number Priority Date Filing Date Title
JP54098906A JPS6056143B2 (ja) 1979-08-02 1979-08-02 アミジン誘導体ならびにその製造法
GB7943945A GB2055800B (en) 1979-08-02 1979-12-20 Guanidinothiazoles and their preparation and use
DE2951675A DE2951675C2 (de) 1979-08-02 1979-12-21 Guanidinothiazolverbindungen, Verfahren zu deren Herstellung und Arzneimittelzubereitungen
PH23454A PH15657A (en) 1979-08-02 1979-12-21 Guanidinothiazole compounds,process for preparation and gastric inhibiting compositions containing them
SE7910568A SE444317B (sv) 1979-08-02 1979-12-21 Nya guanidinotiazolforeningar samt farmaceutiska kompositioner derav
CH11362/79A CH648027A5 (de) 1979-08-02 1979-12-24 Guanidinothiazolverbindungen, verfahren zu deren herstellung und arzneimittelzubereitungen.
NLAANVRAGE7909321,A NL180420C (nl) 1979-08-02 1979-12-27 Farmaceutische preparaten, welke een invloed op de maagzuurafscheiding bezitten en ten minste een guanidinothiazoolderivaat als werkzame stof bevatten alsmede de voor gebruik in dergelijke preparaten geschikte guanidinothiazoolderivaten.
US06/107,629 US4283408A (en) 1979-08-02 1979-12-27 Guanidinothiazole compounds, process for preparation and gastric inhibiting compositions containing them
CA000342699A CA1134836A (en) 1979-08-02 1979-12-28 Process for preparing novel guanidinothiazole compounds
ES487381A ES8100281A1 (es) 1979-08-02 1979-12-28 Un procedimiento para la preparacion de un compuesto de guanidinotiazol
FR797931938A FR2462431B1 (fr) 1979-08-02 1979-12-28 Nouveau compose du guanidinothiazole, son procede de preparation et des compositions medicales contenant de tels composes
IT69498/79A IT1119641B (it) 1979-08-02 1979-12-28 Composti del guanidinotiazolo particolarmente utili come antisecretivi gastrici e procedimento per la loro preparazione
AT0103080A AT374800B (de) 1979-03-06 1980-02-25 Verfahren zur herstellung neuer guanidinothiazole und von deren salzen
FI800591A FI70890C (fi) 1979-03-06 1980-02-27 Foerfarande foer framstaellning av farmakologiskt vaerdefulla guanidinotiazolfoereningar
AU55975/80A AU534329B2 (en) 1979-03-06 1980-02-28 Guanioinothiazoles
GR61334A GR67011B (ja) 1979-03-06 1980-03-03
PT70899A PT70899A (en) 1979-03-06 1980-03-04 Process for preparing useful guanidinothiazole compounds
SU802891152A SU876056A3 (ru) 1979-03-06 1980-03-05 Способ получени гуанидинотиазольных соединений
MX8011198U MX7406E (es) 1979-03-06 1980-03-05 Procedimiento para preparar compuestos de guanidinotiazol
UA2891152A UA5926A1 (uk) 1979-03-06 1980-03-05 Спосіб одержання гуанідінотіазольних сполучень
MX8011289U MX7292E (es) 1979-03-06 1980-03-05 Procedimiento para preparar compuestos de guanidinotiazol
DK093580A DK157132C (da) 1979-03-06 1980-03-05 Analogifremgangsmaade til fremstilling af guanidinothiazolforbindelser eller syreadditionssalte deraf
SI8010622A SI8010622A8 (sl) 1979-03-06 1980-03-06 Postopek pridobivanja gvanidintiazolnih spojin
YU622/80A YU42966B (en) 1979-03-06 1980-03-06 Process for obtaining guanidine thiazole compounds
CA000521982A CA1222763B (en) 1979-08-02 1986-10-31 Process for preparing novel guanidinothiazole compounds
NL930038C NL930038I2 (nl) 1979-08-02 1993-05-19 Farmaceutische preparaten, welke een invloed op demaagzuurafscheiding bezitten en ten minste een qu anidinothiazoolderivaat als werkzame stof bevattenalsmede de voor gebruik in dergelijke preparaten geschikte quanidinothiazoolderivaten.
LV930547A LV5493A3 (lv) 1979-03-06 1993-11-30 Guanidinotiazolu savienojumu iegusanas panemiens
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
JP54098906A JPS6056143B2 (ja) 1979-08-02 1979-08-02 アミジン誘導体ならびにその製造法

Publications (2)

Publication Number Publication Date
JPS5622770A JPS5622770A (en) 1981-03-03
JPS6056143B2 true JPS6056143B2 (ja) 1985-12-09

Family

ID=14232166

Family Applications (1)

Application Number Title Priority Date Filing Date
JP54098906A Expired JPS6056143B2 (ja) 1979-03-06 1979-08-02 アミジン誘導体ならびにその製造法

Country Status (12)

Country Link
US (1) US4283408A (ja)
JP (1) JPS6056143B2 (ja)
CA (2) CA1134836A (ja)
CH (1) CH648027A5 (ja)
DE (1) DE2951675C2 (ja)
ES (1) ES8100281A1 (ja)
FR (1) FR2462431B1 (ja)
GB (1) GB2055800B (ja)
IT (1) IT1119641B (ja)
NL (2) NL180420C (ja)
PH (1) PH15657A (ja)
SE (1) SE444317B (ja)

Families Citing this family (91)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO781300L (no) * 1977-04-20 1978-10-23 Ici Ltd Fremgangsmaate for fremstilling av fysiologisk aktive guanidinderivater
PH16099A (en) * 1979-03-06 1983-06-24 Yamanouchi Pharma Co Ltd Guanidinothiazole compounds,process for preparing them and medical composition containing them
GR71929B (ja) * 1979-11-13 1983-08-19 Ici Ltd
DE3168031D1 (en) * 1980-07-30 1985-02-14 Ici Plc Guanidine derivatives
US4382090A (en) * 1980-10-02 1983-05-03 Eli Lilly And Company N-Thiazolylmethylthioalkyl-N'alkylamidines and related compounds
IN158869B (ja) * 1981-03-18 1987-02-07 Ici Plc
DE3267110D1 (de) * 1981-05-18 1985-12-05 Ici Plc Amidine derivatives
DE3238867A1 (de) * 1982-10-20 1984-04-26 Ludwig Heumann & Co GmbH, 8500 Nürnberg Heterocyclische verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JPS59104370A (ja) * 1982-12-03 1984-06-16 Kotobuki Seiyaku Kk チアゾ−ル誘導体及びその製造方法
JPS59227870A (ja) * 1983-06-07 1984-12-21 Yamanouchi Pharmaceut Co Ltd 新規２−グアニジノチアゾリン誘導体ならびにその製造法
US4497810A (en) * 1983-10-14 1985-02-05 Merck & Co., Inc. Thiatriazine dioxides as gastric anti-secretory agents
US4663347A (en) 1983-10-31 1987-05-05 Merck Frosst Canada, Inc. Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene biosynthesis
CA1269382A (en) * 1984-04-18 1990-05-22 Jose A. Ortiz Anti-ulceric sulfonamidines
US4560690A (en) * 1984-04-30 1985-12-24 Pfizer Inc. 2-(N-substituted guanidino)-4-hetero-arylthiazole antiulcer agents
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GB2055800A (en) 1981-03-11
JPS5622770A (en) 1981-03-03
CA1134836A (en) 1982-11-02
US4283408A (en) 1981-08-11
SE7910568L (sv) 1981-02-03
ES487381A0 (es) 1980-11-01
ES8100281A1 (es) 1980-11-01
DE2951675C2 (de) 1982-07-01
NL7909321A (nl) 1981-02-04
PH15657A (en) 1983-03-11
NL180420C (nl) 1987-02-16
IT1119641B (it) 1986-03-10
FR2462431B1 (fr) 1985-07-26
CH648027A5 (de) 1985-02-28
DE2951675A1 (de) 1981-02-05
FR2462431A1 (fr) 1981-02-13
GB2055800B (en) 1983-05-11
SE444317B (sv) 1986-04-07
NL930038I1 (nl) 1993-08-02
NL180420B (nl) 1986-09-16
IT7969498A0 (it) 1979-12-28
NL930038I2 (nl) 1993-10-01
CA1222763B (en) 1987-06-09

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