DE2635916A1 - Dihydro-1,4-pyridine und diese enthaltende heilmittel - Google Patents
Dihydro-1,4-pyridine und diese enthaltende heilmittelInfo
- Publication number
- DE2635916A1 DE2635916A1 DE19762635916 DE2635916A DE2635916A1 DE 2635916 A1 DE2635916 A1 DE 2635916A1 DE 19762635916 DE19762635916 DE 19762635916 DE 2635916 A DE2635916 A DE 2635916A DE 2635916 A1 DE2635916 A1 DE 2635916A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- dihydro
- formula
- pyridine
- thiomethyl
- 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.)
- Withdrawn
Links
- 229940126601 medicinal product Drugs 0.000 title claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- -1 alkyl acetylacetate Chemical compound 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003254 radicals Chemical group 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000004872 arterial blood pressure Effects 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 210000005240 left ventricle Anatomy 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 210000000709 aorta Anatomy 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000000004 hemodynamic effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000035488 systolic blood pressure Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WJYHCYBNUJVCEH-UHFFFAOYSA-N cyclohexane;ethoxyethane Chemical compound CCOCC.C1CCCCC1 WJYHCYBNUJVCEH-UHFFFAOYSA-N 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 230000003205 diastolic effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 125000000627 niacin group Chemical group 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 230000036581 peripheral resistance Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 210000003752 saphenous vein Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000004873 systolic arterial blood pressure Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33501/75A GB1511694A (en) | 1975-08-12 | 1975-08-12 | Pyridine derivatives |
| GB4518875 | 1975-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2635916A1 true DE2635916A1 (de) | 1977-02-24 |
Family
ID=26261898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762635916 Withdrawn DE2635916A1 (de) | 1975-08-12 | 1976-08-10 | Dihydro-1,4-pyridine und diese enthaltende heilmittel |
Country Status (19)
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001054A3 (de) * | 1977-08-24 | 1979-04-04 | Bayer Ag | 2-Pyridyl-1,4-dihydropyridine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2949464A1 (de) * | 1978-12-18 | 1980-06-26 | Sandoz Ag | Benzoxadiazole und benzothiadiazole, ihre herstellung und verwendung |
| DE2949491A1 (de) * | 1978-12-18 | 1980-06-26 | Sandoz Ag | 1,4-dihydropyridine, ihre herstellung und verwendung |
| EP0083315A3 (en) * | 1981-12-30 | 1983-08-24 | Ciba-Geigy Ag | Pyridyl-n-oxides, processes for their preparation and pharmaceutical compositions containing them |
| EP0088274A1 (de) * | 1982-03-05 | 1983-09-14 | Bayer Ag | Neue 1,4-Dihydropyridine, Verfahren zu ihrer Herstellung und ihrer Verwendung in Arzneimitteln |
| EP0239186A1 (en) * | 1986-02-03 | 1987-09-30 | The Governors of the University of Alberta | Antihypertensive reduced pyridyl derivatives |
| EP0595166A1 (de) * | 1992-10-30 | 1994-05-04 | Bayer Ag | 4-Heterocyclyl substituierte Dihydropyridine |
| US6001857A (en) * | 1992-10-30 | 1999-12-14 | Bayer Aktiengesellschaft | Heterocyclyl substituted dihydropyridines |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4414213A (en) * | 1982-03-22 | 1983-11-08 | Mead Johnson & Company | Dihydropyridyl cyclic imidate esters and their pharmaceutical use |
Family Cites Families (10)
| 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 |
| DE1813436C3 (de) * | 1968-12-07 | 1979-01-11 | Bayer Ag, 5090 Leverkusen | N-Substituierte 2,6-Dimethyl-l,4dihydropyridine |
| DE1923990C3 (de) * | 1969-05-10 | 1978-11-23 | Bayer Ag | Verfahren zur Herstellung von N-substituierten M-Dihydropyridin-S.S-dicarbonsäureestern |
| DE2003146A1 (de) * | 1970-01-24 | 1971-07-29 | Bayer Ag | Neue 1,4-Dihydropyridinderivate |
| DE2005116C3 (de) * | 1970-02-05 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Symmetrische 1,4-Dihydropyridin-3,5-dicarbonsäureester |
| DE2117571C3 (de) * | 1971-04-10 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | Unsymmetrische 1,4-Dihydropyridin-33-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2117573C3 (de) * | 1971-04-10 | 1978-07-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von unsymmetrischen l,4-Dihydropyridin-3,5dicarbonsäureestern, sowie ihre Verwendung als Arzneimittel |
| DE2210672C3 (de) * | 1972-03-06 | 1980-03-20 | Bayer Ag, 5090 Leverkusen | N-substituierte unsymmetrische 1 ^-Dihydropyridin-S^-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2218644C3 (de) * | 1972-04-18 | 1982-08-19 | Bayer Ag, 5090 Leverkusen | Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2248150A1 (de) * | 1972-09-30 | 1974-04-04 | Bayer Ag | Dihydropyridinpolyester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1976
- 1976-07-21 FR FR7622285A patent/FR2320750A1/fr active Granted
- 1976-08-02 AT AT568776A patent/AT351025B/de not_active IP Right Cessation
- 1976-08-04 MX MX002128U patent/MX3464E/es unknown
- 1976-08-04 AU AU16569/76A patent/AU504839B2/en not_active Expired
- 1976-08-05 CH CH1001576A patent/CH612678A5/xx not_active IP Right Cessation
- 1976-08-05 US US05/711,862 patent/US4096270A/en not_active Expired - Lifetime
- 1976-08-06 CA CA258,591A patent/CA1079284A/en not_active Expired
- 1976-08-06 AR AR264249A patent/AR209672A1/es active
- 1976-08-09 ES ES450582A patent/ES450582A1/es not_active Expired
- 1976-08-09 PT PT65456A patent/PT65456B/pt unknown
- 1976-08-10 DE DE19762635916 patent/DE2635916A1/de not_active Withdrawn
- 1976-08-10 DD DD194263A patent/DD126696A5/xx unknown
- 1976-08-11 CS CS765241A patent/CS194774B2/cs unknown
- 1976-08-11 JP JP51095887A patent/JPS5223081A/ja active Granted
- 1976-08-11 SE SE7608959A patent/SE7608959L/xx not_active Application Discontinuation
- 1976-08-11 NO NO762790A patent/NO144457C/no unknown
- 1976-08-11 DK DK362676A patent/DK362676A/da not_active Application Discontinuation
- 1976-08-12 NL NL7608989A patent/NL7608989A/xx unknown
- 1976-08-12 SU SU762386167A patent/SU1007556A3/ru active
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001054A3 (de) * | 1977-08-24 | 1979-04-04 | Bayer Ag | 2-Pyridyl-1,4-dihydropyridine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2949464A1 (de) * | 1978-12-18 | 1980-06-26 | Sandoz Ag | Benzoxadiazole und benzothiadiazole, ihre herstellung und verwendung |
| DE2949491A1 (de) * | 1978-12-18 | 1980-06-26 | Sandoz Ag | 1,4-dihydropyridine, ihre herstellung und verwendung |
| EP0083315A3 (en) * | 1981-12-30 | 1983-08-24 | Ciba-Geigy Ag | Pyridyl-n-oxides, processes for their preparation and pharmaceutical compositions containing them |
| EP0088274A1 (de) * | 1982-03-05 | 1983-09-14 | Bayer Ag | Neue 1,4-Dihydropyridine, Verfahren zu ihrer Herstellung und ihrer Verwendung in Arzneimitteln |
| EP0239186A1 (en) * | 1986-02-03 | 1987-09-30 | The Governors of the University of Alberta | Antihypertensive reduced pyridyl derivatives |
| EP0595166A1 (de) * | 1992-10-30 | 1994-05-04 | Bayer Ag | 4-Heterocyclyl substituierte Dihydropyridine |
| US5502064A (en) * | 1992-10-30 | 1996-03-26 | Bayer Aktiengesellschaft | 4-heterocyclyl-substituted dihydropyridines |
| US6001857A (en) * | 1992-10-30 | 1999-12-14 | Bayer Aktiengesellschaft | Heterocyclyl substituted dihydropyridines |
Also Published As
| Publication number | Publication date |
|---|---|
| ES450582A1 (es) | 1977-11-16 |
| US4096270A (en) | 1978-06-20 |
| AU504839B2 (en) | 1979-11-01 |
| NL7608989A (nl) | 1977-02-15 |
| FR2320750A1 (fr) | 1977-03-11 |
| NO144457B (no) | 1981-05-25 |
| FR2320750B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-09-28 |
| NO144457C (no) | 1981-09-02 |
| AR209672A1 (es) | 1977-05-13 |
| PT65456A (fr) | 1976-09-01 |
| AT351025B (de) | 1979-07-10 |
| CH612678A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-08-15 |
| AU1656976A (en) | 1978-02-09 |
| DD126696A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-03 |
| CS194774B2 (en) | 1979-12-31 |
| NO762790L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-15 |
| CA1079284A (en) | 1980-06-10 |
| JPS5223081A (en) | 1977-02-21 |
| SU1007556A3 (ru) | 1983-03-23 |
| MX3464E (es) | 1980-12-09 |
| DK362676A (da) | 1977-02-13 |
| ATA568776A (de) | 1978-12-15 |
| JPS5422986B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-08-10 |
| PT65456B (fr) | 1978-02-10 |
| SE7608959L (sv) | 1977-02-13 |
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