DE2242787C2 - 4-Phenyl-6-amino-3,4-dihydropyridon-(2)-3,5-dicarbonsäure-diäthylesterderivate, ein Verfahren zu deren Herstellung und diese enthaltende Arzneimittel - Google Patents
4-Phenyl-6-amino-3,4-dihydropyridon-(2)-3,5-dicarbonsäure-diäthylesterderivate, ein Verfahren zu deren Herstellung und diese enthaltende ArzneimittelInfo
- Publication number
- DE2242787C2 DE2242787C2 DE2242787A DE2242787A DE2242787C2 DE 2242787 C2 DE2242787 C2 DE 2242787C2 DE 2242787 A DE2242787 A DE 2242787A DE 2242787 A DE2242787 A DE 2242787A DE 2242787 C2 DE2242787 C2 DE 2242787C2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- diethyl ester
- acid diethyl
- phenyl
- dicarboxylic acid
- 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
- 238000000034 method Methods 0.000 title description 9
- 239000003814 drug Substances 0.000 title description 8
- 230000008569 process Effects 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 230000036772 blood pressure Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- ZPOODPZCZLCUAN-UHFFFAOYSA-N 3,4-dihydro-1h-pyridin-2-one Chemical compound O=C1CCC=CN1 ZPOODPZCZLCUAN-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001409 amidines Chemical class 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- HSDKTLKBDJXJQU-UHFFFAOYSA-N ethyl 3-amino-3-iminopropanoate Chemical compound CCOC(=O)CC(N)=N HSDKTLKBDJXJQU-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- UMLQZEQVUPPDOQ-UHFFFAOYSA-N NC(NC(C1)=O)=CC1C1=CC=CC=C1 Chemical compound NC(NC(C1)=O)=CC1C1=CC=CC=C1 UMLQZEQVUPPDOQ-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 210000003748 coronary sinus Anatomy 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- VQKLRVZQQYVIJW-UHFFFAOYSA-N dihydralazine Chemical compound C1=CC=C2C(NN)=NN=C(NN)C2=C1 VQKLRVZQQYVIJW-UHFFFAOYSA-N 0.000 description 2
- 229960002877 dihydralazine Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PLYNVXKJUKCUOF-UHFFFAOYSA-N 2,3-dihydro-1h-pyridin-4-one Chemical compound O=C1CCNC=C1 PLYNVXKJUKCUOF-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- MJYYTPUBZGNXOH-UHFFFAOYSA-N NC(NC(C1)=O)=CC1C1=CC([N+]([O-])=O)=CC=C1 Chemical compound NC(NC(C1)=O)=CC1C1=CC([N+]([O-])=O)=CC=C1 MJYYTPUBZGNXOH-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003440 anti-fibrillation Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- ADUOLQRHFZGDPM-UHFFFAOYSA-N diethyl 2-[(3-nitrophenyl)methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CC1=CC=CC([N+]([O-])=O)=C1 ADUOLQRHFZGDPM-UHFFFAOYSA-N 0.000 description 1
- VUWPIBNKJSEYIN-UHFFFAOYSA-N diethyl 2-benzylidenepropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CC1=CC=CC=C1 VUWPIBNKJSEYIN-UHFFFAOYSA-N 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- -1 fluoromethylphenyl Chemical group 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000011287 therapeutic dose 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2242787A DE2242787C2 (de) | 1972-08-31 | 1972-08-31 | 4-Phenyl-6-amino-3,4-dihydropyridon-(2)-3,5-dicarbonsäure-diäthylesterderivate, ein Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| US390193A US3925395A (en) | 1972-08-31 | 1973-08-21 | 4-Aryl-6-amino-3,4-dihydropyrid-2-one-3,5-dicarboxylic acid ester |
| CA179,509A CA1016946A (en) | 1972-08-31 | 1973-08-23 | 3,-4-dihydropyridones |
| IL43080A IL43080A (en) | 1972-08-31 | 1973-08-27 | 3,4-dihydropyridones,their production and pharmaceutical compositions containing them |
| NL7311832A NL7311832A (OSRAM) | 1972-08-31 | 1973-08-28 | |
| DD173153A DD109628A5 (OSRAM) | 1972-08-31 | 1973-08-29 | |
| JP9628973A JPS5626661B2 (OSRAM) | 1972-08-31 | 1973-08-29 | |
| LU68325A LU68325A1 (OSRAM) | 1972-08-31 | 1973-08-29 | |
| CH1238973A CH592061A5 (OSRAM) | 1972-08-31 | 1973-08-29 | |
| PL1973164910A PL89430B1 (OSRAM) | 1972-08-31 | 1973-08-29 | |
| BE135060A BE804161A (fr) | 1972-08-31 | 1973-08-29 | Procede de preparation de 3,4-dihydropyridones et medicament contenant ces composes |
| SE7311813A SE385882B (sv) | 1972-08-31 | 1973-08-30 | Sett att framstella nya 3,4-dihydropyridoner |
| DK476573*A DK131855C (da) | 1972-08-31 | 1973-08-30 | Fremgangsmade til fremstilling af 3,4-dihydropyridoner |
| AU59835/73A AU476373B2 (en) | 1972-08-31 | 1973-08-30 | New 3, 4-dihydropyridones, their production, and their medicinal use |
| ES418340A ES418340A1 (es) | 1972-08-31 | 1973-08-30 | Procedimiento para la obtencion de 3,4-dihidropiridonas. |
| HUBA2976A HU167992B (OSRAM) | 1972-08-31 | 1973-08-30 | |
| IE1524/73A IE38141B1 (en) | 1972-08-31 | 1973-08-30 | New 3,4-dihydropyridones their production and their medicinal use |
| ZA735973A ZA735973B (en) | 1972-08-31 | 1973-08-30 | New 3,4-dihydropyridones,their production and their medicinal use |
| GB4084873A GB1389505A (en) | 1972-08-31 | 1973-08-30 | 3,4-dihydropyridones their production and their medicinal use |
| AT760073A AT327902B (de) | 1972-08-31 | 1973-08-31 | Verfahren zur herstellung von neuen 3,4-dihydropyridonen |
| FR7331531A FR2197598B1 (OSRAM) | 1972-08-31 | 1973-08-31 | |
| US05/531,525 US3951992A (en) | 1972-08-31 | 1974-12-11 | 4-Thenyl-or furyl-6-amino-3,4-dihydropyrid-2-one-3,5-dicarboxylic acid ester |
| US05/531,599 US3951991A (en) | 1972-08-31 | 1974-12-11 | 4-Aryl-6-amino-3,4-dihydropyrid-2-one-3,5-dicarboxylic acid ester |
| US05/531,999 US3951990A (en) | 1972-08-31 | 1974-12-12 | 4-Aryl or hetero-6-amino-3,4-dihydropyrid-2-one-3,5-dicarboxylic acid ester |
| US05/531,906 US3987176A (en) | 1972-08-31 | 1974-12-12 | Composition and use of 3,4-dihydropyridones as vasodilators and antihypertensive agents |
| US05/596,507 US3981882A (en) | 1972-08-31 | 1975-07-16 | Process for preparing 4-aryl of hetero-6-amino-3,4-dihydropyrid-2-one-3,5-dicarboxylic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2242787A DE2242787C2 (de) | 1972-08-31 | 1972-08-31 | 4-Phenyl-6-amino-3,4-dihydropyridon-(2)-3,5-dicarbonsäure-diäthylesterderivate, ein Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2242787A1 DE2242787A1 (de) | 1974-03-14 |
| DE2242787C2 true DE2242787C2 (de) | 1982-01-21 |
Family
ID=5855065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2242787A Expired DE2242787C2 (de) | 1972-08-31 | 1972-08-31 | 4-Phenyl-6-amino-3,4-dihydropyridon-(2)-3,5-dicarbonsäure-diäthylesterderivate, ein Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3925395A (OSRAM) |
| JP (1) | JPS5626661B2 (OSRAM) |
| AT (1) | AT327902B (OSRAM) |
| AU (1) | AU476373B2 (OSRAM) |
| BE (1) | BE804161A (OSRAM) |
| CA (1) | CA1016946A (OSRAM) |
| CH (1) | CH592061A5 (OSRAM) |
| DD (1) | DD109628A5 (OSRAM) |
| DE (1) | DE2242787C2 (OSRAM) |
| DK (1) | DK131855C (OSRAM) |
| ES (1) | ES418340A1 (OSRAM) |
| FR (1) | FR2197598B1 (OSRAM) |
| GB (1) | GB1389505A (OSRAM) |
| HU (1) | HU167992B (OSRAM) |
| IE (1) | IE38141B1 (OSRAM) |
| IL (1) | IL43080A (OSRAM) |
| LU (1) | LU68325A1 (OSRAM) |
| NL (1) | NL7311832A (OSRAM) |
| PL (1) | PL89430B1 (OSRAM) |
| SE (1) | SE385882B (OSRAM) |
| ZA (1) | ZA735973B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002762A (en) * | 1973-03-03 | 1977-01-11 | Bayer Aktiengesellschaft | 2-Amino-3,4-dihydropyridines used to effect coronary vessel dilation and treat hypertension |
| IT8367883A0 (it) * | 1982-08-23 | 1983-08-22 | Rorer Int Overseas | Composti cardiotonici del 2 piridone 5 biciclico eteroaril sostituito e relative composizioni farmaceutiche |
| WO1993009774A1 (en) * | 1991-11-18 | 1993-05-27 | G.D. Searle & Co. | 2-(4-substituted)phenylmethylene derivatives and methods of use |
| CA2496815C (en) | 2002-08-27 | 2011-04-26 | Bayer Healthcare Ag | Dihydropyridinone derivatives |
| US20050252833A1 (en) * | 2004-05-14 | 2005-11-17 | Doyle James A | Process and apparatus for converting oil shale or oil sand (tar sand) to oil |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1923990C3 (de) * | 1969-05-10 | 1978-11-23 | Bayer Ag | Verfahren zur Herstellung von N-substituierten M-Dihydropyridin-S.S-dicarbonsäureestern |
| DE2013431C3 (de) * | 1970-03-20 | 1979-12-20 | Bayer Ag, 5090 Leverkusen | 4-Azidophenyl-l,4-dihydropyridin-3,5-dicarbonsäureester |
| DE2003146A1 (de) * | 1970-01-24 | 1971-07-29 | Bayer Ag | Neue 1,4-Dihydropyridinderivate |
-
1972
- 1972-08-31 DE DE2242787A patent/DE2242787C2/de not_active Expired
-
1973
- 1973-08-21 US US390193A patent/US3925395A/en not_active Expired - Lifetime
- 1973-08-23 CA CA179,509A patent/CA1016946A/en not_active Expired
- 1973-08-27 IL IL43080A patent/IL43080A/en unknown
- 1973-08-28 NL NL7311832A patent/NL7311832A/xx not_active Application Discontinuation
- 1973-08-29 BE BE135060A patent/BE804161A/xx unknown
- 1973-08-29 CH CH1238973A patent/CH592061A5/xx not_active IP Right Cessation
- 1973-08-29 JP JP9628973A patent/JPS5626661B2/ja not_active Expired
- 1973-08-29 PL PL1973164910A patent/PL89430B1/pl unknown
- 1973-08-29 DD DD173153A patent/DD109628A5/xx unknown
- 1973-08-29 LU LU68325A patent/LU68325A1/xx unknown
- 1973-08-30 SE SE7311813A patent/SE385882B/xx unknown
- 1973-08-30 GB GB4084873A patent/GB1389505A/en not_active Expired
- 1973-08-30 IE IE1524/73A patent/IE38141B1/xx unknown
- 1973-08-30 ES ES418340A patent/ES418340A1/es not_active Expired
- 1973-08-30 ZA ZA735973A patent/ZA735973B/xx unknown
- 1973-08-30 AU AU59835/73A patent/AU476373B2/en not_active Expired
- 1973-08-30 HU HUBA2976A patent/HU167992B/hu unknown
- 1973-08-30 DK DK476573*A patent/DK131855C/da active
- 1973-08-31 FR FR7331531A patent/FR2197598B1/fr not_active Expired
- 1973-08-31 AT AT760073A patent/AT327902B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1016946A (en) | 1977-09-06 |
| PL89430B1 (OSRAM) | 1976-11-30 |
| FR2197598B1 (OSRAM) | 1977-07-15 |
| ES418340A1 (es) | 1976-03-16 |
| IE38141B1 (en) | 1978-01-04 |
| GB1389505A (en) | 1975-04-03 |
| DK131855B (da) | 1975-09-15 |
| DE2242787A1 (de) | 1974-03-14 |
| HU167992B (OSRAM) | 1976-02-28 |
| BE804161A (fr) | 1974-02-28 |
| IL43080A (en) | 1977-01-31 |
| JPS5626661B2 (OSRAM) | 1981-06-19 |
| AU476373B2 (en) | 1976-09-16 |
| ZA735973B (en) | 1974-10-30 |
| US3925395A (en) | 1975-12-09 |
| AU5983573A (en) | 1975-03-06 |
| FR2197598A1 (OSRAM) | 1974-03-29 |
| IL43080A0 (en) | 1973-11-28 |
| DD109628A5 (OSRAM) | 1974-11-12 |
| ATA760073A (de) | 1975-05-15 |
| IE38141L (en) | 1974-02-28 |
| AT327902B (de) | 1976-02-25 |
| DK131855C (da) | 1976-02-16 |
| SE385882B (sv) | 1976-07-26 |
| JPS4962483A (OSRAM) | 1974-06-17 |
| LU68325A1 (OSRAM) | 1973-10-30 |
| CH592061A5 (OSRAM) | 1977-10-14 |
| NL7311832A (OSRAM) | 1974-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |