IE63111B1 - Dihydropyridine derivatives, their preparation and their use - Google Patents
Dihydropyridine derivatives, their preparation and their useInfo
- Publication number
- IE63111B1 IE63111B1 IE270687A IE270687A IE63111B1 IE 63111 B1 IE63111 B1 IE 63111B1 IE 270687 A IE270687 A IE 270687A IE 270687 A IE270687 A IE 270687A IE 63111 B1 IE63111 B1 IE 63111B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- compound
- formula
- acid
- pharmaceutically acceptable
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 11
- 125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 title description 8
- 229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
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- 238000000034 method Methods 0.000 claims description 10
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- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical class OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 210000001774 pressoreceptor Anatomy 0.000 description 1
- KSZOTXZFYCRWQK-JYRVWZFOSA-N propan-2-yl (2z)-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate Chemical compound CC(C)OC(=O)C(\C(C)=O)=C/C1=CC=CC([N+]([O-])=O)=C1 KSZOTXZFYCRWQK-JYRVWZFOSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
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
- C07D211/80—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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (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)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE940210A IE77041B1 (en) | 1986-10-09 | 1987-10-09 | Dihydropyridine derivatives their preparation and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24025486 | 1986-10-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE872706L IE872706L (en) | 1988-04-09 |
| IE63111B1 true IE63111B1 (en) | 1995-03-22 |
Family
ID=17056752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE270687A IE63111B1 (en) | 1986-10-09 | 1987-10-09 | Dihydropyridine derivatives, their preparation and their use |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4772596A (en, 2012) |
| EP (2) | EP0266922B1 (en, 2012) |
| JP (1) | JPS63253082A (en, 2012) |
| KR (1) | KR920004483B1 (en, 2012) |
| CN (1) | CN1017897B (en, 2012) |
| AT (2) | ATE94162T1 (en, 2012) |
| AU (1) | AU600038B2 (en, 2012) |
| CA (1) | CA1309098C (en, 2012) |
| DE (2) | DE3751978T2 (en, 2012) |
| DK (1) | DK170891B1 (en, 2012) |
| ES (2) | ES2059391T3 (en, 2012) |
| FI (1) | FI90543C (en, 2012) |
| GR (1) | GR3022301T3 (en, 2012) |
| HU (1) | HU199454B (en, 2012) |
| IE (1) | IE63111B1 (en, 2012) |
| NO (1) | NO170084C (en, 2012) |
| NZ (1) | NZ222106A (en, 2012) |
| RU (1) | RU1831476C (en, 2012) |
| ZA (1) | ZA877518B (en, 2012) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2671349B1 (fr) * | 1991-01-09 | 1993-04-23 | Lafon Labor | Nouveaux derives de 1,4-dihydropyridine, leur procede de preparation et composition therapeutique les contenant. |
| US5310917A (en) * | 1991-09-13 | 1994-05-10 | Merck & Co., Inc. | Process for the preparation of 4-substituted-1,4-dihydropydrines |
| IL152021A0 (en) * | 2000-04-11 | 2003-04-10 | Sankyo Co | Pharmaceutical compositions containing pyridine derivatives |
| AU2001284413A1 (en) * | 2000-08-30 | 2002-03-13 | Sankyo Company Limited | Medicinal compositions for preventing or treating heart failure |
| TWI341312B (en) | 2002-12-24 | 2011-05-01 | Sankyo Co | Optical active dihydropyridine derivatives |
| JP4546726B2 (ja) * | 2002-12-24 | 2010-09-15 | 宇部興産株式会社 | 光学活性なジヒドロピリジン誘導体 |
| BRPI0406987A (pt) * | 2003-01-31 | 2006-01-10 | Sankyo Co | Medicamento para a prevenção e/ou tratamento de arteriosclerose, medicamentos para a inibição de proliferação de células do músculo liso vascular, de formação de neoìntima dos vasos sanguìneos e de remodelação vascular, medicamento para a prevenção de restenose que segue intervenção coronária percutânea, e, medicamentos para a profilaxia e/ou tratamento de hipertensão ou doenças causadas por hipertensão ou doenças causadas por hipertensão, de doenças cardìacas, de angina do peito, de infarto miocárdico, de arritmia, de morte súbita, de insuficiência cardìaca, de hipertrofia cardìaca, de doenças renais, de nefropatia diabética, de glomerulonefrite, de nefrosclerose, de doenças cerebrovasculares, de infarto cerebral, e de hemorragia cerebral |
| JP4629973B2 (ja) * | 2003-09-22 | 2011-02-09 | 第一三共株式会社 | 光学活性シクロプロピルアミン誘導体およびその製造方法 |
| EP1693364B1 (en) * | 2003-12-12 | 2015-05-20 | Daiichi Sankyo Company, Limited | Intermediates for the production of optically active cyclopropylamine derivatives and process for the production of the intermediates |
| JP2008543862A (ja) * | 2005-06-15 | 2008-12-04 | エラン ファーマ インターナショナル リミテッド | ナノ粒子アゼルニジピン製剤 |
| BRPI0612674B8 (pt) * | 2005-06-27 | 2021-05-25 | Daiichi Sankyo Co Ltd | preparação farmacêutica, uso de um antagonista do receptor de angiotensina ii e um bloqueador do canal de cálcio |
| CN100352818C (zh) * | 2005-09-23 | 2007-12-05 | 四川科伦药业股份有限公司 | 一种改进的制备阿折地平的方法 |
| TW200736245A (en) * | 2005-11-29 | 2007-10-01 | Sankyo Co | Acid addition salts of optically active dihydropyridine derivatives |
| TW200806648A (en) * | 2005-11-29 | 2008-02-01 | Sankyo Co | Acid addition salts of dihydropyridine derivatives |
| TWI399223B (zh) * | 2006-09-15 | 2013-06-21 | Daiichi Sankyo Co Ltd | 奧美沙坦酯及氨氯地平之固體劑型 |
| JP2008290989A (ja) * | 2007-05-28 | 2008-12-04 | Ube Ind Ltd | ジヒドロピリジン誘導体の酸付加塩を含有する医薬 |
| JP2008290988A (ja) * | 2007-05-28 | 2008-12-04 | Ube Ind Ltd | 光学活性なジヒドロピリジン誘導体の酸付加塩を含有する医薬 |
| IT1391113B1 (it) * | 2008-09-30 | 2011-11-18 | Dipharma Francis Srl | Procedimento per la preparazione di azelnidipina cristallina |
| JP5463051B2 (ja) * | 2009-02-17 | 2014-04-09 | 相模化成工業株式会社 | １，４―ジヒドロピリジン誘導体の製造法 |
| CN101863879B (zh) * | 2009-04-16 | 2012-12-19 | 四川科伦药物研究有限公司 | 一种α晶型阿折地平的制备方法 |
| JP2011006379A (ja) * | 2009-05-26 | 2011-01-13 | Tokuyama Corp | ｛２−アミノ−１，４−ジヒドロ−６−メチル−４−（３−ニトロフェニル）−３，５−ピリジンジカルボン酸３−（１−ジフェニルメチルアゼチジン−３−イル）エステル５−イソプロピルエステル｝（アゼルニジピン）の再結晶方法、アゼルニジピンのイソプロピルアルコール付加体、およびアゼルニジピンの製造方法 |
| JP2011105649A (ja) * | 2009-11-18 | 2011-06-02 | Daito Kk | アゼルニジピンの結晶 |
| JP5637710B2 (ja) * | 2010-03-24 | 2014-12-10 | 株式会社トクヤマ | ｛２−アミノ−１，４−ジヒドロ−６−メチル−４−（３−ニトロフェニル）−３，５−ピリジンジカルボン酸３−（１−ジフェニルメチルアゼチジン−３−イル）エステル５−イソプロピルエステル｝の製造方法 |
| JP2012020970A (ja) * | 2010-07-15 | 2012-02-02 | Tokuyama Corp | ｛２−アミノ−１，４−ジヒドロ−６−メチル−４−（３−ニトロフェニル）−３，５−ピリジンジカルボン酸３−（１−ジフェニルメチルアゼチジン−３−イル）エステル５−イソプロピルエステル｝の製造方法 |
| EP2703398B1 (en) * | 2011-04-29 | 2017-12-13 | Xuanzhu Pharma Co., Ltd. | 1,4-dihydropyridine -3,5-dicarboxylate derivatives, preparation methods and uses thereof |
| JP5917034B2 (ja) * | 2011-07-15 | 2016-05-11 | ニプロ株式会社 | カルシウムブロッカーを含有する固形医薬組成物 |
| RU2570752C2 (ru) | 2011-08-26 | 2015-12-10 | Вокхардт Лимитед | Способы лечения сердечно-сосудистых нарушений |
| CN102329259B (zh) * | 2011-10-21 | 2013-09-18 | 南京工业大学 | (1-二苯甲基-3-吖丁啶醇)氰基乙酸酯的制备方法 |
| CN102382104A (zh) * | 2011-11-21 | 2012-03-21 | 山东新华制药股份有限公司 | α晶型阿折地平的制备方法 |
| CN103319457B (zh) * | 2012-03-20 | 2016-01-27 | 北京晶润宏达医药科技有限公司 | 阿折地平γ晶型的制备方法 |
| WO2017063307A1 (zh) * | 2015-10-13 | 2017-04-20 | 山东轩竹医药科技有限公司 | 1，4-二氢吡啶-3，5-二羧酸酯衍生物的制备方法及中间体 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| ZA7152B (en) * | 1970-01-24 | 1971-10-27 | Bayer Ag | New pharmaceutically active 1,4-dihydropyridines |
| US3935223A (en) * | 1972-03-06 | 1976-01-27 | Bayer Aktiengesellschaft | 2-Amino-1,4-dihydropyridine derivatives |
| GB1455502A (en) * | 1973-02-20 | 1976-11-10 | Yamanouchi Pharma Co Ltd | 1,4-dihydropyridine derivatives |
| JPS55301A (en) * | 1978-02-14 | 1980-01-05 | Yamanouchi Pharmaceut Co Ltd | 1,4-dihydropyridine-3,5-dicarboxylic ester derivative and its preparation |
| JPS57171968A (en) * | 1981-04-17 | 1982-10-22 | Kyowa Hakko Kogyo Co Ltd | 1,4-dihydropyridine derivative |
| 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 |
| DE3244178A1 (de) * | 1982-11-30 | 1984-05-30 | Bayer Ag, 5090 Leverkusen | 1,4-dihydropyridinderivate, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| EP0125803A3 (en) * | 1983-04-27 | 1987-01-21 | FISONS plc | Pharmaceutically active dihydropyridines |
| GB8314744D0 (en) * | 1983-05-27 | 1983-07-06 | Fujisawa Pharmaceutical Co | 2 6-disubstituted-1 4-dihydropyridine derivative |
| 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 |
| ES8708211A1 (es) * | 1985-06-14 | 1987-10-01 | Sankyo Co | Un procedimiento para la preparacion de nuevos derivados de 4-(fenil sustituido)-1,4-dihidropiridina. |
-
1987
- 1987-10-05 US US07/105,388 patent/US4772596A/en not_active Expired - Lifetime
- 1987-10-06 KR KR1019870011142A patent/KR920004483B1/ko not_active Expired
- 1987-10-07 ZA ZA877518A patent/ZA877518B/xx unknown
- 1987-10-08 RU SU874203529A patent/RU1831476C/ru active
- 1987-10-08 JP JP62254085A patent/JPS63253082A/ja active Granted
- 1987-10-09 DE DE3751978T patent/DE3751978T2/de not_active Expired - Lifetime
- 1987-10-09 AU AU79537/87A patent/AU600038B2/en not_active Expired
- 1987-10-09 AT AT87308976T patent/ATE94162T1/de not_active IP Right Cessation
- 1987-10-09 CA CA000548953A patent/CA1309098C/en not_active Expired - Lifetime
- 1987-10-09 HU HU874578A patent/HU199454B/hu unknown
- 1987-10-09 AT AT92202251T patent/ATE146169T1/de not_active IP Right Cessation
- 1987-10-09 DE DE87308976T patent/DE3787346T2/de not_active Expired - Lifetime
- 1987-10-09 IE IE270687A patent/IE63111B1/en not_active IP Right Cessation
- 1987-10-09 NO NO874219A patent/NO170084C/no unknown
- 1987-10-09 EP EP87308976A patent/EP0266922B1/en not_active Expired - Lifetime
- 1987-10-09 EP EP92202251A patent/EP0529702B1/en not_active Expired - Lifetime
- 1987-10-09 NZ NZ222106A patent/NZ222106A/xx unknown
- 1987-10-09 ES ES87308976T patent/ES2059391T3/es not_active Expired - Lifetime
- 1987-10-09 CN CN87107150A patent/CN1017897B/zh not_active Expired
- 1987-10-09 DK DK529987A patent/DK170891B1/da not_active IP Right Cessation
- 1987-10-09 FI FI874451A patent/FI90543C/fi not_active IP Right Cessation
- 1987-10-09 ES ES92202251T patent/ES2097859T3/es not_active Expired - Lifetime
-
1997
- 1997-01-16 GR GR970400061T patent/GR3022301T3/el unknown
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| 古林隆司 et al. | Novel 2-Amino-1, 4-dihydropyridine Calcium Antagonists. II. Synthesis and Antihypertensive Effects of 2-Amino-1, 4-dihydropyridine Derivatives Having N, N-Dialkylaminoalkoxycarbonyl Groups at 3-and/or 5-Position. | |
| EP0127150A2 (en) | 2,6-Disubstituted-1,4-dihydropyridine derivative, process for the preparation of the same and pharmaceutical composition comprising the same | |
| JPH0160466B2 (en, 2012) |
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| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |