JPH0625091B2 - ジヒドロジベンゾシクロヘプチリデン―エチルアミン誘導体その製法ならびに医薬組成物 - Google Patents

ジヒドロジベンゾシクロヘプチリデン―エチルアミン誘導体その製法ならびに医薬組成物

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Publication number
JPH0625091B2
JPH0625091B2 JP59163743A JP16374384A JPH0625091B2 JP H0625091 B2 JPH0625091 B2 JP H0625091B2 JP 59163743 A JP59163743 A JP 59163743A JP 16374384 A JP16374384 A JP 16374384A JP H0625091 B2 JPH0625091 B2 JP H0625091B2
Authority
JP
Japan
Prior art keywords
hydrogen atom
formula
methyl group
dihydrodibenzocycloheptylidene
alkyl
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 - Lifetime
Application number
JP59163743A
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English (en)
Other versions
JPS60126265A (ja
Inventor
デイ．キレラ クサビエル
アール．アンドレオリ ロメオ
ピー．ロベラス ペドロ
ブルセギーニ レオニダ
ピー．イルーレ ジヨセ
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.)
ESUPANYORA DE ESUPESHIARIDAADESU FUARUMAKO TERAPYUUTEIKASU SA SOC
Original Assignee
ESUPANYORA DE ESUPESHIARIDAADESU FUARUMAKO TERAPYUUTEIKASU SA SOC
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Application filed by ESUPANYORA DE ESUPESHIARIDAADESU FUARUMAKO TERAPYUUTEIKASU SA SOC filed Critical ESUPANYORA DE ESUPESHIARIDAADESU FUARUMAKO TERAPYUUTEIKASU SA SOC
Publication of JPS60126265A publication Critical patent/JPS60126265A/ja
Publication of JPH0625091B2 publication Critical patent/JPH0625091B2/ja
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
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    • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/52—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

Description

【発明の詳細な説明】 技術分野 本発明はジヒドロジベンゾシクロヘプチリデンエチルア
ミンから誘導せられる抗潰瘍作用を有する新規化合物、
その製薬的に許容せられる塩ならびにそれらの製法およ
びそれらを主成分とする抗潰瘍剤に関するものである。
従来技術 ジャーナル オブ オルガニック ケミストリー２７
巻、２３０−２４０頁（１９６２年）にはジベンゾ
［ａ，ｄ］−１，４−シクロヘプタジエン誘導体の抗う
つ作用が記載されている。
米国特許第４，３８１，３０５号にはある種１，２−エ
チレンジアミン誘導体の脈管抗痙れんならびに抗アレル
ギー作用が示され、米国特許第４，３０８，３８７号に
は抗精神病作用をもつある種のジフェニルブチルピペラ
ジンカルボキシルアミド誘導体が記載されている。
さらに欧州特許第５６６１６号には抗ヒスタミン作用を
もつある種のシクロヘプテン誘導体が示されている。
抗潰瘍剤として多くの薬剤が知られており、例えばラニ
チジン、シメチジン等があげられるが、これらの薬効は
必ずしも満足すべきものではない。
発明が解決しようとする問題点 従って、本発明目的は特に抗潰瘍剤として有効な新規化
合物を提供するにある。
問題点を解決するための手段 本発明に従えば、上記目的が、 式（Ｉ） （式中、Ｒ1は水素原子あるいはメチル基；Ｒ2は水素原
子あるいはメチル基；またＲ3は水素原子、炭素数１〜
４のアルキル基あるいは−ＣＯ（Ｃ１〜Ｃ４アルキル）
基を表す） で表されるジヒドロジベンゾシクロヘプチリデン−エチ
ルアミン誘導体ならびにその製薬的に許容せられる塩に
より達成せられる。
式（Ｉ）で表される本発明に係る化合物は文献未記載で
あり、 式（II） （式中、Ｒ1は水素原子あるいはメチル基；Ｒ2は水素原
子あるいはメチル基；Ｒ3は水素原子、炭素数１〜４の
アルキル基あるいは−ＣＯ（Ｃ１〜Ｃ４アルキル）基） で示されるアミンと、式（III） （式中、ＷはＣｌあるいはＢｒ） で示されるハロゲン化合物を反応させ、所望によりその
製薬的に許容せられる塩に導くことを特徴とする方法に
より工業的有利に製造せられる。
この反応は不活性溶媒中、脱ハロゲン化水素剤、例えば
無機あるいは有機の塩基の存在下に、あるいは原料アミ
ンを過剰量用いて実施せられる。あるいはまた本発明に
係る式（Ｉ）で表される化合物は式（II）で表されるア
ミンと式（IV） で示されるアルデヒドをトナリウム ボロハイドライド
の如き還元剤の存在下あるいは接触水添条件下に反応さ
せることによっても製造しうる。
式（Ｉ）で表される化合物は所望により、鉱酸例えば塩
酸、硫酸あるいは硝酸または有機酸例えば修酸、サリチ
ル酸、クエン酸、マレイン酸、フマール酸により製薬的
に許容せられる塩に変えられる。しかしながら製薬上特
に塩酸塩あるいはマレイン酸であることが好ましい。
本発明に係る化合物（Ｉ）およびその塩は脈管拡張、分
泌抑制、抗喘息、抗うつ作用等各種の有用な薬理作用を
示すが、特に抗潰瘍作用に優れている。以下実施例によ
り本発明を説明する。
以下の記載に於いて、簡便を期すため式（Ｉ）で表され
る化合物を「ＷＡＳ−」の次に各々特定数字を付して表
すこととする。
実施例１ Ｎ−２−（１０，１１−ジヒドロジベンゾ−（ａ，ｄ）
−シクロヘプチ−５−イリデン）−エチルエフエドリン
の製造 本化合物をＷＡＳ−４３０４と略称する。
５．１０ｇ（２０ミリモル）の２−クロロ−１−（１
０，１１−ジヒドロジベンゾ−（ａ，ｄ）−シクロヘプ
チ−５−イリデン）−エタンと６．６０ｇ（４０ミリモ
ル）のエフエドリン塩基の混合物をアセトニトリル１０
０ｍｌ中で４時間還流した。冷却後、溶媒を除去し、残
渣をクロロホルムにとり、１０％塩酸で洗った。有機抽
出液を無水硫酸ナトリウムで乾燥させ、溶媒を除き、残
渣をアセトニトリルから再結晶させ、５．０３ｇのＮ−
２−（１０，１１−ジヒドロジベンゾ−（ａ，ｄ）−シ
クロヘプチ−５−イリデン）−エチルエフエドリンを得
た。収率 ６２％ 分析データ 融点 ２３１〜２３２℃ ＩＲ ３３７０，２６２０，２５１０， １６００，１４８５，７７５， ７６０，７４５，７０５ ＮＭＲ 7.4/sc(13H),6.4/t(1H),6.0/t(1H), 5.5/sc(1H),2.5〜4.2/sc(8H) 下記第１表に本発明化合物の製造例である実施例２〜４
を示す。各々、化学構造および分析データが示されてお
り、又その製法も実施例１の方法によることを示してあ
る。
ＮＭＲはプロトン核磁気共鳴スペクトルを表し、このＮ
ＭＲ分析では下記が表示されている。
まずシグナルの位置（ｐｐｍ）（スケールα）、次にこ
のシグナルの形あるいはマルチプリシテイが下記略号で
示されている。即ち、 Ｓ・・・・単一線 ｄ・・・・二重線 ｔ・・・・三重線 ｇ・・・・四重線 Ｓｃ・・・コンプレックスシグナル ｓａ・・・ブロードシグナル エレクトロニツク インテグレーションで得られる各シ
グナルに対応するプロトン数が( )内に記載されてい
る。
薬理学的性質 本発明化合物は広範な薬理学的性質をもつ。例えば血管
拡張作用、抗潰瘍作用、抗分泌作用、抗喘息作用、抗ヒ
スタミン作用、抗抑圧作用等を有する。就中抗潰瘍作用
は顕著であり医薬として有用である。
抗潰瘍作用 ケーピー バーガバ等のEur.J.Pharm.22,191〜195(197
3)記載の方法に従いラットでのインドメタシン誘引潰瘍
に対する括抗作用しらべた。抗潰瘍作用でのＥＤ50を作
用の強力な化合物につき計算し、残りの化合物では標準
薬剤との対比で＋記号を用い作用の強さを示した。
同表において、効力の強さは＋記号数に比例して示さ
れ、最大の＋＋＋＋は現在用いられている標準的薬剤と
匹敵する効力を表す。
＋＋＋＋ 極めて強い作用 ＋＋＋ 顕著な作用 ＋＋ 中等度の作用 ＋ 弱い作用 〇 作用なし この試験ではラニチジンとシメチジンを標準薬剤として
使用している。
スイス マイスに腹腔内投与し、毒性をしらべた。投与
７日後の致死率及びＬＤ50をしらべ、例えば最も代表的
なＷＡＳ−４３０４でＬＤ50は１１５ｍｇ／ｋｇ i.p.
であった。
医学的用途 本発明に係る化合物は下記治療ならびに予防目的で使用
せられる。
胃ならびに十二指腸潰瘍、ゾリンガー・エリソン症候
群、胃粘膜層の損傷による消化系出血、再発性ならび接
合手術後の潰瘍、胃食道炎の治療。
剤形ならびに用量 本発明化合物は薬剤的ならびに治療的に受け入れられる
あらゆる形態の剤形で、適切な用量で用いられる。これ
らには錠剤、糖衣錠、ピル、カプセル、粉末、シロップ
等の経口投与薬、坐薬、注射液等の非経口投与薬が含ま
れる。有効成分の一日投与量は、適切症状ならびに剤型
によりことなるが０．１ｍｇ〜１５００ｍｇの広範囲内
で適宜選択せられる。
───────────────────────────────────────────────────── フロントページの続き (72)発明者 ペドロ ピー．ロベラス スペイン国 バルセロナ、カレ ビブレツ ト タラサ、94 (72)発明者 レオニダ ブルセギーニ スペイン国 バルセロナ カレ カポナ タ、５ (72)発明者 ジヨセ ピー．イルーレ スペイン国 バルセロナ カレ マヨーデ サリア、184 (56)参考文献 米国特許4381305（ＵＳ，Ａ) Ｔｈｅ Ｊｏｕｒｎａｌ ｏｆ Ｏｒｇ ａｎｉｃ Ｃｈｅｍｉｓｔｒｙ 27 Ｐ. 230−240 （1962)

Claims (4)

    【特許請求の範囲】
  1. 【請求項１】式（Ｉ） （式中、Ｒ1は水素原子あるいはメチル基；Ｒ2は水素原
    子あるいはメチル基；またＲ3は水素原子、炭素数１〜
    ４のアルキル基あるいは−ＣＯ（Ｃ１〜Ｃ４アルキル）
    基を表す） で表されるジヒドロジベンゾシクロヘプチリデン−エチ
    ルアミン誘導体ならびにその製薬的に許容せられる塩。
  2. 【請求項２】式（II） （式中、Ｒ1は水素原子あるいはメチル基；Ｒ2は水素原
    子あるいはメチル基；Ｒ3は水素原子、炭素数１〜４の
    アルキル基あるいは−ＣＯ（Ｃ１〜Ｃ４アルキル）基） で示されるアミンと、式（III） （式中、ＷはＣｌあるいはＢｒ） で示されるハロゲン化合物を反応させ、所望によりその
    製薬的に許容せられる塩に導くことを特徴とする式
    （Ｉ） （式中、Ｒ1、Ｒ2およびＲ3は夫々前述せる通り）で表
    されるジヒドロジベンゾシクロヘプチリデン−エチルア
    ミン誘導体あるいはその製薬的に許容せられる塩の製造
    方法。
  3. 【請求項３】式（Ｉ） （式中、Ｒ1は水素原子あるいはメチル基；Ｒ2は水素原
    子あるいはメチル基；またＲ3は水素原子、炭素数１〜
    ４のアルキル基あるいは−ＣＯ（Ｃ１〜Ｃ４アルキル）
    基） で表されるジヒドロジベンゾシクロヘプチリデン−エチ
    ルアミン誘導体もしくはその製薬的に許容せられる塩を
    有効成分として含み、製剤用キャリヤーを含む抗潰瘍
    剤。
  4. 【請求項４】Ｒ1とＲ2が夫々メチル基で、Ｒ3が水素原
    子である特許請求の範囲第１項記載の化合物。
JP59163743A 1983-08-02 1984-08-02 ジヒドロジベンゾシクロヘプチリデン―エチルアミン誘導体その製法ならびに医薬組成物 Expired - Lifetime JPH0625091B2 (ja)

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ES524680A ES524680A0 (es) 1983-08-02 1983-08-02 Procedimiento de obtencion de nuevos compuestos derivados de la difenil-metilen-etilamina.
ES524680 1983-08-02

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JPH0625091B2 true JPH0625091B2 (ja) 1994-04-06

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US (3) US4835156A (ja)
EP (2) EP0357956A3 (ja)
JP (1) JPH0625091B2 (ja)
KR (1) KR900007198B1 (ja)
AT (1) ATE59632T1 (ja)
AU (1) AU580963B2 (ja)
CA (1) CA1243018A (ja)
DE (1) DE3483798D1 (ja)
ES (1) ES524680A0 (ja)
NZ (1) NZ208691A (ja)
ZA (1) ZA845940B (ja)

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NZ208691A (en) 1989-06-28
AU3131684A (en) 1985-02-07
ATE59632T1 (de) 1991-01-15
US4835179A (en) 1989-05-30
EP0132764A3 (en) 1985-12-04
JPS60126265A (ja) 1985-07-05
US5112826A (en) 1992-05-12
US4835156A (en) 1989-05-30
KR900007198B1 (ko) 1990-10-05
ES8502099A1 (es) 1984-12-16
CA1243018A (en) 1988-10-11
DE3483798D1 (de) 1991-02-07
KR850002261A (ko) 1985-05-10
EP0132764A2 (en) 1985-02-13
EP0357956A3 (en) 1990-08-29
EP0357956A2 (en) 1990-03-14
AU580963B2 (en) 1989-02-09
ES524680A0 (es) 1984-12-16
ZA845940B (en) 1986-08-27

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