JPH02348B2 - - Google Patents

Info

Publication number
JPH02348B2
JPH02348B2 JP56056937A JP5693781A JPH02348B2 JP H02348 B2 JPH02348 B2 JP H02348B2 JP 56056937 A JP56056937 A JP 56056937A JP 5693781 A JP5693781 A JP 5693781A JP H02348 B2 JPH02348 B2 JP H02348B2
Authority
JP
Japan
Prior art keywords
compound
present
broad
dihydropyridine
chem
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
JP56056937A
Other languages
English (en)
Other versions
JPS57171968A (en
Inventor
Kenji Muto
Minoru Watanabe
Takao Hatsuta
Susumu Sugaya
Nobutaka Takemoto
Yoshihiro Nakamizo
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.)
KH Neochem Co Ltd
Original Assignee
Kyowa Hakko Kogyo 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=13041432&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JPH02348(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Kyowa Hakko Kogyo Co Ltd filed Critical Kyowa Hakko Kogyo Co Ltd
Priority to JP56056937A priority Critical patent/JPS57171968A/ja
Priority to US06/367,995 priority patent/US4448964A/en
Priority to EP82103166A priority patent/EP0063365B2/en
Priority to DE8282103166T priority patent/DE3265978D1/de
Publication of JPS57171968A publication Critical patent/JPS57171968A/ja
Publication of JPH02348B2 publication Critical patent/JPH02348B2/ja
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

【発明の詳細な説明】 本発明は１，４―ジヒドロピリジン誘導体およ
びその塩に関する。さらに、詳しくは、 式（） で表わされる１，４―ジヒドロピリジン誘導体お
よびその塩に関する。 本発明化合物は、冠血管拡張および末梢血管拡
張作用、血圧降下作用などを有し、抗狭心症薬、
高血圧治療薬などとして有用な化合物である。 従来、１，４―ジヒドロピリジン誘導体のなか
でも特に、２，６―ジメチル―４―（２―ニトロ
フエニル）―１，４―ジヒドロピリジン―３，５
―ジカルボン酸ジメチルエステル（一般名：ニフ
エジピンが冠血管拡張作用、血圧降下作用などを
有する化合物として知られている。 本発明者らは、血圧降下作用を有する新規な化
合物を検索した結果、式（）で表わされる新規
な１，４―ジヒドロピリジン誘導体およびその塩
が優れた血圧降下作用を有し、しかも持続性も優
れていることを見出し本発明が完成した。 以下に本発明を詳細に説明する。 式（）で表わされる１，４―ジヒドロピリジ
ン誘導体の塩の好適な例としては、医薬として許
容される塩、例えば、無機酸塩（例えば塩酸塩、
臭化水素酸塩、りん酸塩、硫酸塩など）および有
機酸塩（例えば、ぎ酸塩、酢酸塩、フマル酸塩、
マレイン酸塩、リンゴ酸塩、アスパラギン酸塩、
グルタミン酸塩など）が挙げられる。 次に、本発明化合物の主な製法を例示する。 製法１：（H.Herbert Fox et al.，J.Org.Chem.
16，1259（1951）に記載されている方法
に準じた方法である。） さらに製法１を詳細に説明する。 原料化合物，およびの混合モル比は
1.0：0.8：0.8〜1.0：4.0：4.0の範囲、好ましくは
1.0：0.9：0.9〜1.0：1.5：1.5の範囲である。 反応は、溶媒、例えば、メタノール、エタノー
ル、イソプロパノール等のアルコール類、ベンゼ
ン、トルエン等の芳香族炭化水素、クロロホル
ム、四塩化炭素等のハロゲン化炭化水素、テトラ
ヒドロフラン、ジオキサン等のエーテル類、アセ
トニトリル、ジメチルホルムアミド等の非プロト
ン性極性溶媒などを使用して、室温〜150℃、好
ましくは30〜100℃で行われる。反応混合物から
目的物の分離は、濃縮、抽出、カラムクロマトグ
ラフイー、再結晶等の通常の操作によつて行われ
る。 さらに、製法２―５を反応式で例示する。 製法２：（B.Loev.et al.，J.Medicinal Chem.17，
956（1974）に記載されている方法に準じ
た方法である。） 化合物＋化合物＋CH3COCH2COOCH3＋
NH3（またはアンモニウム塩）→本発明化合物 製法：３（M.Iwanami et al.，Chem.Pham.
Bull.27，1426（1979）に記載された方法
に準じた方法である。） 製法４：（M.Iwanami et al.，Chem.Pharm.
Bull.27，1426（1979）に記載された方法
に準じた方法である。） 化合物＋CH3COCH2COOCH3＋NH3（または
アンモニウム塩）→本発明化合物 製法５：（T.Shibanuma et al.，Chem.Pharm.
Bull，28，2809（1980）に記載された方
法に準じた方法である。） 次に本発明化合物の血圧降下作用を示す。 血圧降下作用 自然発症高血圧ラツト（SHR）に、被検化合
物を0.5％CMC生理食塩水溶液に懸濁した液を経
口投与し、自動血圧記録計（植田製作所）により
尾動脈の収縮期圧を測定する。結果を表１に示
す。 【表】 表１から本発明化合物が対照薬ＡおよびＢに比べ
て優れた血圧降下作用を有し、持続性も優れてい
る化合物であることは明らかである。 以下に実施例および参考例により本発明を説明
する。 実施例 ｍ―ニトロベンズアルデヒド3.02ｇ、β―アミ
ノクロトン酸メチル2.53ｇ及び後記参考例で得ら
れたアセト酢酸Ｎ―ベンジル―３―ピペリジニル
エステル5.5ｇをテトラヒドロフラン10mlに加え、
19時間還流下撹拌する。 反応液を減圧下濃縮し、シリカゲルカラムクロ
マトグラフイー（溶出液クロロホルム：メタノー
ル＝20：1v／ｖ）によつて目的物を分離する。
目的物を含む分画を濃縮後、アセトン25mlに溶解
し、これに塩化水素飽和エーテルを加え酸性にす
ると黄色結晶が析出する。結晶を過、乾燥し
て、黄色の２，６―ジメチル―４―（３―ニトロ
フエニル）―１，４―ジヒドロピリジン―３，５
―ジカルボン酸―３―（Ｎ―ベンジル―３―ピペ
リジニル）エステル―５―メチルエステル塩酸塩
2.10ｇ（収率19.4％）を得る。 融点：176.0〜178.0℃ IRスペクトル（KBr，cm-1）：1670〜1690，
1525，1345 NMRスペクトル（DMSO・d6）：1.33〜2.17
（4H，broad），2.33（6H，ｓ），2.70〜3.36
（4H，broad），3.57（3H，ｓ），4.40（2H，
ｓ），4.98（1H，ｓ），5.20（1H，broad），
7.30〜8.20（9H，ｍ），9.4（1H，broad） 元素分析値（C28H32N3O6Clとして）： Ｃ Ｈ Ｎ 実測値（％）：61.72 6.01 7.72 計算値（％）：62.04 5.96 7.75 参考例 ３―ヒドロキシピペリジン塩酸塩15.0ｇ、塩化
ベンジル13.8ｇ、トリエチルアミン22.1ｇ及びト
ルエン120mlの混合物を還流下４時間撹拌する。
反応液を過後、液を濃縮し、減圧蒸留により
１―ベンジル―３―ヒドロキシピペリジン11.8ｇ
（収率56.9％）を得る。 融点：125〜126℃／3.5mmHg NMRスペクトル（CCl4，δ）：1.30〜1.90（4H，
broad），2.20〜2.50（4H，brod），3.45
（2H，ｓ），3.40〜3.90（1H，broad），7.20
（5H，ｓ） 上記反応生成物11.8ｇと触媒量のトリエチルア
ミンをテトラヒドロフラン10mlに溶解し、その溶
液へデケテン5.6ｇを15分で滴下する。滴下後、
室温で1.5時間、ついで50〜60℃で、4.5時間反応
させる。反応液を濃縮後、シリカゲルカラムクロ
マトグラフイー（溶出液クロロホルム：メタノー
ル＝９：1v／ｖ）により、精製したアセト酢酸
―Ｎ―ベンジル―３―ピペリジニルエステル
10.65ｇ（収率62.5％）を得る。 このものは蒸留せずに実施例の反応に用いた。 NMRスペクトル（CDCl3，δ）：1.30〜1.90（4H，
broad），2.10〜2.95（4H，broad），2.27
（3H，ｓ），3.43（2H，ｓ），3.54（2H，
ｓ），4.73〜5.2（1H，broad），7.30（5H，
ｓ）

Claims (1)

  1. 【特許請求の範囲】 １ 式 で表わされる１，４―ジヒドロピリジン誘導体お
    よびその塩。
JP56056937A 1981-04-17 1981-04-17 1,4-dihydropyridine derivative Granted JPS57171968A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP56056937A JPS57171968A (en) 1981-04-17 1981-04-17 1,4-dihydropyridine derivative
US06/367,995 US4448964A (en) 1981-04-17 1982-04-13 1,4-Dihydropyridine derivatives
EP82103166A EP0063365B2 (en) 1981-04-17 1982-04-15 1,4-Dihydropyridine derivative and pharmaceutical composition containing same
DE8282103166T DE3265978D1 (en) 1981-04-17 1982-04-15 1,4-dihydropyridine derivative and pharmaceutical composition containing same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP56056937A JPS57171968A (en) 1981-04-17 1981-04-17 1,4-dihydropyridine derivative

Publications (2)

Publication Number Publication Date
JPS57171968A JPS57171968A (en) 1982-10-22
JPH02348B2 true JPH02348B2 (ja) 1990-01-08

Family

ID=13041432

Family Applications (1)

Application Number Title Priority Date Filing Date
JP56056937A Granted JPS57171968A (en) 1981-04-17 1981-04-17 1,4-dihydropyridine derivative

Country Status (4)

Country Link
US (1) US4448964A (ja)
EP (1) EP0063365B2 (ja)
JP (1) JPS57171968A (ja)
DE (1) DE3265978D1 (ja)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1983003249A1 (en) * 1982-03-17 1983-09-29 Yoshitomi Pharmaceutical 1,4-dihydropyridine-3,5-dicarboxylate derivatives
JPS59225162A (ja) * 1983-06-03 1984-12-18 Kyowa Hakko Kogyo Co Ltd １，４−ジヒドロピリジン誘導体
JPS5970667A (ja) * 1982-10-15 1984-04-21 Kyowa Hakko Kogyo Co Ltd １，４−ジヒドロピリジン誘導体
AU557175B2 (en) * 1982-10-15 1986-12-11 Kyowa Hakko Kogyo Co. Ltd. 2,6-dimethyl-4-(3-nitro phenyl)-1,4-dihydro pyridine-3,5- dicarboxylic acid esters
JPS5970666A (ja) * 1982-10-15 1984-04-21 Kyowa Hakko Kogyo Co Ltd １，４−ジヒドロピリジン誘導体
US4603135A (en) * 1983-10-17 1986-07-29 Takeda Chemical Industries, Ltd. Substituted piperazinyl alkyl esters of 2-amino-4-aryl-1,4-dihydro-6-alkyl-3,5-pyridinedicarboxylates
US4755512A (en) * 1984-04-11 1988-07-05 Bristol-Myers Company Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moities
US4895846A (en) * 1984-04-11 1990-01-23 Bristol-Myers Company Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moieties
IT1196272B (it) * 1984-09-28 1988-11-16 Poli Ind Chimica Spa Derivati di 1,4-diidropiridina e composizioni farmaceutiche che li contengono
JPS61158962A (ja) * 1985-01-07 1986-07-18 Teijin Ltd １，４−ジヒドロピリジン誘導体の製造法
US4833150A (en) * 1985-03-14 1989-05-23 Nelson Research & Development Co. 1,4-dihydropyridines
JPS6289662A (ja) * 1985-06-14 1987-04-24 Sankyo Co Ltd １，４−ジヒドロピリジン誘導体
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JPS6248626A (ja) * 1986-08-29 1987-03-03 Kyowa Hakko Kogyo Co Ltd １，４−ジヒドロピリジン誘導体
US4772596A (en) * 1986-10-09 1988-09-20 Sankyo Company Limited Dihydropyridine derivatives, their preparation and their use
US6471980B2 (en) 2000-12-22 2002-10-29 Avantec Vascular Corporation Intravascular delivery of mycophenolic acid
US7018405B2 (en) 2000-12-22 2006-03-28 Avantec Vascular Corporation Intravascular delivery of methylprednisolone
GEP20084406B (en) * 2003-05-30 2008-06-25 Ranbaxy Lab Ltd Substituted pyrrole derivatives and their use as hmg-co inhibitors
AU2006313430B2 (en) * 2005-11-08 2012-09-06 Ranbaxy Laboratories Limited Process for (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4- [(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3, 5-dihydroxy-heptanoic acid hemi calcium salt
WO2008020314A2 (en) * 2006-03-14 2008-02-21 Ranbaxy Laboratories Limited Statin stabilizing dosage formulations
AU2007274724B2 (en) * 2006-07-14 2012-07-26 Ranbaxy Laboratories Limited Polymorphic forms of an HMG-CoA reductase inhibitor and uses thereof
WO2012123966A1 (en) 2011-03-04 2012-09-20 Arch Pharmalabs Limited Process for the preparation of 4 -substituted -1, 4-dihydropyridines
CN102746215A (zh) * 2011-04-18 2012-10-24 张兆勇 一种制备高纯度盐酸贝尼地平的方法
WO2012147103A2 (en) 2011-04-25 2012-11-01 Council Of Scientific & Industrial Research PROCESS FOR CONTINUOUS FLOW SYNTHESIS OF β-ΑΜΙΝΟ CROTONATE
WO2013030725A1 (en) 2011-08-26 2013-03-07 Wockhardt Limited Methods for treating cardiovascular disorders
CN104529872B (zh) * 2014-12-10 2018-07-10 天津长源医药科技有限公司 一种盐酸贝尼地平中间体的合成方法
WO2019053491A1 (en) 2017-09-15 2019-03-21 Deva Holding Anonim Sirketi CRYSTALLINE BENIDIPINE HCL SOLID FORMS AND PROCESSES FOR PREPARING THE SAME
CN114907256B (zh) * 2022-04-18 2024-01-12 苏州东瑞制药有限公司 一种盐酸贝尼地平的制备方法

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Also Published As

Publication number Publication date
US4448964A (en) 1984-05-15
EP0063365B1 (en) 1985-09-04
JPS57171968A (en) 1982-10-22
EP0063365A1 (en) 1982-10-27
DE3265978D1 (en) 1985-10-10
EP0063365B2 (en) 1994-06-15

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