DE2949491A1 - 1,4-dihydropyridine, ihre herstellung und verwendung - Google Patents
1,4-dihydropyridine, ihre herstellung und verwendungInfo
- Publication number
- DE2949491A1 DE2949491A1 DE19792949491 DE2949491A DE2949491A1 DE 2949491 A1 DE2949491 A1 DE 2949491A1 DE 19792949491 DE19792949491 DE 19792949491 DE 2949491 A DE2949491 A DE 2949491A DE 2949491 A1 DE2949491 A1 DE 2949491A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- compounds
- compound
- iii
- 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.)
- Granted
Links
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 2
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YBBRQAXNTWMMFZ-UHFFFAOYSA-N 2,1,3-benzoxadiazole-4-carbaldehyde Chemical compound O=CC1=CC=CC2=NON=C12 YBBRQAXNTWMMFZ-UHFFFAOYSA-N 0.000 description 1
- ZYXNLVMBIHVDRH-UHFFFAOYSA-N 2-Methylpropyl 3-oxobutanoate Chemical compound CC(C)COC(=O)CC(C)=O ZYXNLVMBIHVDRH-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 230000002213 calciumantagonistic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH548480A CH654836A5 (en) | 1979-12-08 | 1980-07-17 | Heterocyclic organic compounds and therapeutic agents containing them |
| PH24383A PH19536A (en) | 1977-06-20 | 1980-08-01 | Benzoxadiazoles and benzothiadiazoles and pharmaceutical composition containing them |
| MX9203580A MX9203580A (es) | 1979-12-08 | 1992-06-26 | 1,4-dihidropiridinas y composiciones farmaceuticas que las contienen. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1283578A CH639659A5 (de) | 1978-12-18 | 1978-12-18 | Neue 1,4-dihydropyridinderivate, deren herstellung und verwendung. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2949491A1 true DE2949491A1 (de) | 1980-06-26 |
| DE2949491C2 DE2949491C2 (enrdf_load_stackoverflow) | 1988-10-27 |
Family
ID=4386824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792949491 Granted DE2949491A1 (de) | 1977-06-20 | 1979-12-08 | 1,4-dihydropyridine, ihre herstellung und verwendung |
Country Status (18)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3136031A1 (de) * | 1980-09-18 | 1982-04-08 | Sandoz-Patent-GmbH, 7850 Lörrach | Pharmazeutische zusammensetzungen, wirksam gegen koronare herzkrankheiten und hohen blutdruck |
| EP0042089A3 (en) * | 1980-06-12 | 1982-09-22 | Bayer Ag | 4-heterocylic substituted dihydropyridines, processes for preparing them, their therapeutical use and their preparation |
| FR2528431A1 (fr) * | 1982-06-15 | 1983-12-16 | Sandoz Sa | Nouveaux derives de la 1,4-dihydropyridine, leur preparation et leur utilisation comme medicaments |
| AT384219B (de) * | 1982-06-15 | 1987-10-12 | Sandoz Ag | Herstellung von neuen 1,4-dihydropyridinderivaten in optisch aktiver oder racematform |
| WO1994001405A1 (de) * | 1992-07-10 | 1994-01-20 | Siegfried Goldmann | Lichtaktivierbare 1-(2-nitrobenzyl)-substituierte 1,4-dihydropyridine |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3269219D1 (en) * | 1981-11-17 | 1986-03-27 | Fisons Plc | Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals |
| ZA83959B (en) * | 1982-03-10 | 1984-09-26 | Sandoz Ltd | 1,4-dihydropyridine derivatives,their preparation and pharmaceutical compositions containing them |
| US4414213A (en) * | 1982-03-22 | 1983-11-08 | Mead Johnson & Company | Dihydropyridyl cyclic imidate esters and their pharmaceutical use |
| JPS5978186A (ja) * | 1982-10-27 | 1984-05-04 | Yoshitomi Pharmaceut Ind Ltd | １，４−ジヒドロピリジン−３，５−ジカルボン酸エステル誘導体 |
| US4794111A (en) * | 1984-05-23 | 1988-12-27 | Bayer Aktiengesellschaft | Dihydropyridine preparations containing β-blockers |
| NL194389C (nl) * | 1984-06-14 | 2002-03-04 | Novartis Ag | Werkwijze voor het bereiden van een vaste dispersie van een farmaceutisch actief middel dat een lage oplosbaarheid in water heeft, in een vaste matrix van een in water oplosbaar polyalkyleenglycol als drager. |
| US5260321A (en) * | 1984-11-12 | 1993-11-09 | Sandoz Ltd. | Use of 1,4-dihydropyridine derivatives and combinations thereof with calcitonins |
| NL194822C (nl) * | 1985-10-01 | 2003-04-03 | Novartis Ag | Preparaat voor orale toediening met geregelde afgifte en werkwijze voor de bereiding ervan. |
| DE3542794A1 (de) * | 1985-12-04 | 1987-06-11 | Bayer Ag | Antihypertensives kombinationspraeparat |
| GB8626217D0 (en) * | 1986-11-03 | 1986-12-03 | Sandoz Ltd | Pharmaceutical compositions |
| US4816263A (en) * | 1987-10-02 | 1989-03-28 | Alza Corporation | Dosage form for treating cardiovascular diseases comprising isradipine |
| KR940003492B1 (ko) * | 1988-10-27 | 1994-04-23 | 주식회사 유한양행 | 1,4-디하이드로피리딘유도체 및 그의 제조방법 |
| KR20040088519A (ko) | 2002-02-22 | 2004-10-16 | 뉴 리버 파마슈티칼스, 인크. | 활성 제제 전달 시스템 및 활성 제제의 보호 및 투여 방법 |
| AU2003269482A1 (en) * | 2003-09-10 | 2005-03-29 | Shasun Chemicals And Drugs Limited | Process for the manufacture of 2,1,3-benzoxadiazole-4-carboxaldehyde |
| CN103613584B (zh) * | 2013-11-27 | 2016-04-27 | 沈阳药科大学 | 一种伊拉地平合成产物后处理的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670824A1 (de) * | 1967-03-20 | 1971-04-01 | Bayer Ag | Verfahren zur Herstellung von 1,4-Dihydropyridinderivaten |
| DE2635916A1 (de) * | 1975-08-12 | 1977-02-24 | Hexachimie | Dihydro-1,4-pyridine und diese enthaltende heilmittel |
| DE2616991A1 (de) * | 1976-04-17 | 1977-10-27 | Bayer Ag | Heterocyclisch-substituierte schwefelhaltige dihydropyridine, mehrere verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5373327A (en) * | 1976-12-13 | 1978-06-29 | Matsushita Electric Ind Co Ltd | Power source system |
| DK149855C (da) * | 1977-06-20 | 1987-04-21 | Sandoz Ag | Analogifremgangsmaade til fremstilling af 1,4-dihydropyridinderivater |
-
1978
- 1978-12-18 CH CH1283578A patent/CH639659A5/de not_active IP Right Cessation
-
1979
- 1979-12-08 DE DE19792949491 patent/DE2949491A1/de active Granted
- 1979-12-11 SE SE7910188A patent/SE445219B/sv not_active IP Right Cessation
- 1979-12-13 BE BE1/9643A patent/BE880591A/fr not_active IP Right Cessation
- 1979-12-14 NL NL7909024A patent/NL193066C/nl not_active IP Right Cessation
- 1979-12-14 IT IT51095/79A patent/IT1164097B/it active Protection Beyond IP Right Term
- 1979-12-14 CY CY1321A patent/CY1321A/en unknown
- 1979-12-14 GB GB7943113A patent/GB2037766B/en not_active Expired
- 1979-12-14 GB GB08215988A patent/GB2103203B/en not_active Expired
- 1979-12-17 IE IE2445/79A patent/IE49496B1/en not_active IP Right Cessation
- 1979-12-17 AU AU53896/79A patent/AU536055B2/en not_active Expired
- 1979-12-17 FR FR7930829A patent/FR2444681A1/fr active Granted
- 1979-12-17 NZ NZ192422A patent/NZ192422A/xx unknown
- 1979-12-17 JP JP16396579A patent/JPS5583783A/ja active Granted
- 1979-12-18 ZA ZA00796842A patent/ZA796842B/xx unknown
-
1985
- 1985-12-20 SG SG975/85A patent/SG97585G/en unknown
- 1985-12-30 MY MY130/85A patent/MY8500130A/xx unknown
-
1986
- 1986-01-08 KE KE3593A patent/KE3593A/xx unknown
- 1986-03-06 HK HK160/86A patent/HK16086A/xx not_active IP Right Cessation
-
1999
- 1999-05-11 NL NL990014C patent/NL990014I1/nl unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670824A1 (de) * | 1967-03-20 | 1971-04-01 | Bayer Ag | Verfahren zur Herstellung von 1,4-Dihydropyridinderivaten |
| DE2635916A1 (de) * | 1975-08-12 | 1977-02-24 | Hexachimie | Dihydro-1,4-pyridine und diese enthaltende heilmittel |
| DE2616991A1 (de) * | 1976-04-17 | 1977-10-27 | Bayer Ag | Heterocyclisch-substituierte schwefelhaltige dihydropyridine, mehrere verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Non-Patent Citations (3)
| Title |
|---|
| BURGER: Medicinal Chemistry, 4. Aufl., Bd. 3, S.319, (gutachtlich genannt) * |
| EP-PS 150 (gutachtlich genannt) * |
| J. of Cardiovescular Pharmacology, 6, 407, 1984 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0042089A3 (en) * | 1980-06-12 | 1982-09-22 | Bayer Ag | 4-heterocylic substituted dihydropyridines, processes for preparing them, their therapeutical use and their preparation |
| DE3136031A1 (de) * | 1980-09-18 | 1982-04-08 | Sandoz-Patent-GmbH, 7850 Lörrach | Pharmazeutische zusammensetzungen, wirksam gegen koronare herzkrankheiten und hohen blutdruck |
| FR2528431A1 (fr) * | 1982-06-15 | 1983-12-16 | Sandoz Sa | Nouveaux derives de la 1,4-dihydropyridine, leur preparation et leur utilisation comme medicaments |
| WO1984000033A1 (fr) * | 1982-06-15 | 1984-01-05 | Sandoz Ag | Derives de 1,4-dihydro-pyridine, leur preparation et compositions pharmaceutiques les contenant |
| AT384219B (de) * | 1982-06-15 | 1987-10-12 | Sandoz Ag | Herstellung von neuen 1,4-dihydropyridinderivaten in optisch aktiver oder racematform |
| WO1994001405A1 (de) * | 1992-07-10 | 1994-01-20 | Siegfried Goldmann | Lichtaktivierbare 1-(2-nitrobenzyl)-substituierte 1,4-dihydropyridine |
| US5606066A (en) * | 1992-07-10 | 1997-02-25 | Goldmann; Siegfried | Light activable "caged" 1-(2-nitrobenzyl)-substituted 1,4-dihydropyridines |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2444681B1 (enrdf_load_stackoverflow) | 1982-10-29 |
| NL7909024A (nl) | 1980-06-20 |
| GB2037766B (en) | 1983-02-16 |
| CH639659A5 (de) | 1983-11-30 |
| IE792445L (en) | 1980-06-18 |
| SG97585G (en) | 1986-07-18 |
| NZ192422A (en) | 1982-09-14 |
| ZA796842B (en) | 1981-07-29 |
| IT1164097B (it) | 1987-04-08 |
| BE880591A (fr) | 1980-06-13 |
| MY8500130A (en) | 1985-12-31 |
| FR2444681A1 (fr) | 1980-07-18 |
| IT7951095A0 (it) | 1979-12-14 |
| AU536055B2 (en) | 1984-04-19 |
| NL193066B (nl) | 1998-05-06 |
| SE7910188L (sv) | 1980-06-19 |
| DE2949491C2 (enrdf_load_stackoverflow) | 1988-10-27 |
| AU5389679A (en) | 1980-06-26 |
| GB2103203A (en) | 1983-02-16 |
| CY1321A (en) | 1986-06-27 |
| SE445219B (sv) | 1986-06-09 |
| NL990014I1 (nl) | 1999-07-01 |
| GB2037766A (en) | 1980-07-16 |
| NL193066C (nl) | 1998-09-08 |
| JPS5583783A (en) | 1980-06-24 |
| JPH0369910B2 (enrdf_load_stackoverflow) | 1991-11-05 |
| GB2103203B (en) | 1983-06-08 |
| IE49496B1 (en) | 1985-10-16 |
| KE3593A (en) | 1986-02-07 |
| HK16086A (en) | 1986-03-14 |
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