DE2949491C2 - - Google Patents
Info
- Publication number
- DE2949491C2 DE2949491C2 DE2949491A DE2949491A DE2949491C2 DE 2949491 C2 DE2949491 C2 DE 2949491C2 DE 2949491 A DE2949491 A DE 2949491A DE 2949491 A DE2949491 A DE 2949491A DE 2949491 C2 DE2949491 C2 DE 2949491C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- compound
- compounds according
- compounds
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 230000017531 blood circulation Effects 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 210000003205 muscle Anatomy 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-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
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229960001597 nifedipine Drugs 0.000 description 3
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229940127291 Calcium channel antagonist Drugs 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
- 241000282326 Felis catus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002213 calciumantagonistic effect Effects 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
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 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
- 230000003257 anti-anginal effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000000916 dilatatory effect Effects 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
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000015220 hamburgers Nutrition 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- -1 methyl β- aminocrotonic acid Chemical compound 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004895 regional blood flow Effects 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
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (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 DE2949491A1 (de) | 1980-06-26 |
| DE2949491C2 true 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3317691A1 (de) * | 1982-03-22 | 1984-11-22 | Bristol-Myers Co., New York, N.Y. | Cyclische dihydropyridylimidatester, verfahren zu ihrer herstellung und pharmazeutische mittel |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3022030A1 (de) * | 1980-06-12 | 1981-12-17 | Bayer Ag, 5090 Leverkusen | 4-thiazol- bzw. 4-imidazol-substituierte, 1,4-dihydropyridine, verfahren zu deren herstellung sowie diese enthaltende arzneimittel |
| CH655658B (enrdf_load_stackoverflow) * | 1980-09-18 | 1986-05-15 | ||
| 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 |
| FR2528431B1 (fr) * | 1982-06-15 | 1986-01-10 | Sandoz Sa | Nouveaux derives de la 1,4-dihydropyridine, leur preparation et leur utilisation comme medicaments |
| IL68975A (en) * | 1982-06-15 | 1987-01-30 | Sandoz Ag | 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid ester derivatives in optically active form,their preparation and pharmaceutical compositions containing them |
| 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 |
| DE4222770A1 (de) * | 1992-07-10 | 1994-01-13 | Bayer Ag | Lichtaktivierbare 1-(2-Nitrobenzyl)-substituierte 1,4-Dihydropyridine |
| JP4625637B2 (ja) | 2002-02-22 | 2011-02-02 | シャイア エルエルシー | 活性物質送達系及び活性物質を保護し投与する方法 |
| WO2005023787A1 (en) * | 2003-09-10 | 2005-03-17 | 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670824C3 (de) * | 1967-03-20 | 1978-08-03 | Bayer Ag, 5090 Leverkusen | 1,4-Dihydropyridin-33-dicarbonsäurealkylester |
| FR2320750A1 (fr) * | 1975-08-12 | 1977-03-11 | Hexachimie | Dihydro-1,4 pyridines et leur application therapeutique |
| DE2616991A1 (de) * | 1976-04-17 | 1977-10-27 | Bayer Ag | Heterocyclisch-substituierte schwefelhaltige dihydropyridine, mehrere verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| JPS5373327A (en) * | 1976-12-13 | 1978-06-29 | Matsushita Electric Ind Co Ltd | Power source system |
| FI64938C (fi) * | 1977-06-20 | 1984-02-10 | Sandoz Ag | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara bensoxa- och bensotiadiazolyl-1,4-dihydropyridinderivat |
-
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 GB GB7943113A patent/GB2037766B/en not_active Expired
- 1979-12-14 NL NL7909024A patent/NL193066C/nl not_active IP Right Cessation
- 1979-12-14 GB GB08215988A patent/GB2103203B/en not_active Expired
- 1979-12-14 IT IT51095/79A patent/IT1164097B/it active Protection Beyond IP Right Term
- 1979-12-14 CY CY1321A patent/CY1321A/en unknown
- 1979-12-17 NZ NZ192422A patent/NZ192422A/xx unknown
- 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 IE IE2445/79A patent/IE49496B1/en not_active IP Right Cessation
- 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3317691A1 (de) * | 1982-03-22 | 1984-11-22 | Bristol-Myers Co., New York, N.Y. | Cyclische dihydropyridylimidatester, verfahren zu ihrer herstellung und pharmazeutische mittel |
Also Published As
| Publication number | Publication date |
|---|---|
| NL193066C (nl) | 1998-09-08 |
| HK16086A (en) | 1986-03-14 |
| JPH0369910B2 (enrdf_load_stackoverflow) | 1991-11-05 |
| DE2949491A1 (de) | 1980-06-26 |
| GB2037766B (en) | 1983-02-16 |
| NL990014I1 (nl) | 1999-07-01 |
| KE3593A (en) | 1986-02-07 |
| JPS5583783A (en) | 1980-06-24 |
| IE49496B1 (en) | 1985-10-16 |
| GB2103203B (en) | 1983-06-08 |
| SE445219B (sv) | 1986-06-09 |
| SG97585G (en) | 1986-07-18 |
| CH639659A5 (de) | 1983-11-30 |
| GB2037766A (en) | 1980-07-16 |
| BE880591A (fr) | 1980-06-13 |
| AU536055B2 (en) | 1984-04-19 |
| FR2444681A1 (fr) | 1980-07-18 |
| NL7909024A (nl) | 1980-06-20 |
| ZA796842B (en) | 1981-07-29 |
| FR2444681B1 (enrdf_load_stackoverflow) | 1982-10-29 |
| SE7910188L (sv) | 1980-06-19 |
| IT1164097B (it) | 1987-04-08 |
| IT7951095A0 (it) | 1979-12-14 |
| NL193066B (nl) | 1998-05-06 |
| GB2103203A (en) | 1983-02-16 |
| CY1321A (en) | 1986-06-27 |
| IE792445L (en) | 1980-06-18 |
| NZ192422A (en) | 1982-09-14 |
| AU5389679A (en) | 1980-06-26 |
| MY8500130A (en) | 1985-12-31 |
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