FI101377B - Menetelmä N-alkyloitujen 1,4-dihydropyridiiniyhdisteiden valmistamisek si - Google Patents
Menetelmä N-alkyloitujen 1,4-dihydropyridiiniyhdisteiden valmistamisek si Download PDFInfo
- Publication number
- FI101377B FI101377B FI911700A FI911700A FI101377B FI 101377 B FI101377 B FI 101377B FI 911700 A FI911700 A FI 911700A FI 911700 A FI911700 A FI 911700A FI 101377 B FI101377 B FI 101377B
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- formula
- general formula
- dihydropyridine
- ester
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 27
- 230000008569 process Effects 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- -1 benzylidene compound Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- OIORMXXUKIGDHC-UHFFFAOYSA-N diethyl 1-cyclopropyl-2,6-dimethyl-4-[4-(trifluoromethyl)phenyl]-4h-pyridine-3,5-dicarboxylate Chemical compound CC1=C(C(=O)OCC)C(C=2C=CC(=CC=2)C(F)(F)F)C(C(=O)OCC)=C(C)N1C1CC1 OIORMXXUKIGDHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 3
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 1
- UNQWSIBNMPYECZ-UHFFFAOYSA-N dimethyl 1,2-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C=1CNC=C(C=1)C(=O)OC UNQWSIBNMPYECZ-UHFFFAOYSA-N 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 abstract description 7
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- 229940079593 drug Drugs 0.000 abstract description 4
- 230000004089 microcirculation Effects 0.000 abstract description 4
- SYHPGXUWPYJXOO-UHFFFAOYSA-N 1,4-dihydropyridine-2,3-dicarboxylic acid Chemical class OC(=O)C1=C(C(O)=O)NC=CC1 SYHPGXUWPYJXOO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000013543 active substance Substances 0.000 abstract description 2
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 9
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000037396 body weight Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- AVFYPHPSIBAAME-UHFFFAOYSA-N dimethyl 1,2,6-trimethyl-4-[4-(trifluoromethyl)phenyl]-4h-pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)N(C)C(C)=C(C(=O)OC)C1C1=CC=C(C(F)(F)F)C=C1 AVFYPHPSIBAAME-UHFFFAOYSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002587 anti-hemolytic effect Effects 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 230000010221 calcium permeability Effects 0.000 description 3
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
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- 239000000203 mixture Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 2
- 108091006112 ATPases Proteins 0.000 description 2
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010054147 Hemoglobins Proteins 0.000 description 2
- 102000001554 Hemoglobins Human genes 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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- GYWPWUWXZRKZQL-UHFFFAOYSA-N dimethyl 4-(4-bromophenyl)-1,2,6-trimethyl-4h-pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)N(C)C(C)=C(C(=O)OC)C1C1=CC=C(Br)C=C1 GYWPWUWXZRKZQL-UHFFFAOYSA-N 0.000 description 2
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 2
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- HNFCWFPZYSJCMI-UHFFFAOYSA-N propyl 3-(4-bromophenyl)prop-2-enoate Chemical compound CCCOC(=O)C=CC1=CC=C(Br)C=C1 HNFCWFPZYSJCMI-UHFFFAOYSA-N 0.000 description 1
- PWZUUYSISTUNDW-VAFBSOEGSA-N quinestrol Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@]4(O)C#C)C)CC2=CC=3OC1CCCC1 PWZUUYSISTUNDW-VAFBSOEGSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000036262 stenosis Effects 0.000 description 1
- 208000037804 stenosis Diseases 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4011695A DE4011695A1 (de) | 1990-04-11 | 1990-04-11 | Verwendung von n-alkylierten 1,4-dihydropyridindicarbonsaeureestern als arzneimittel, neue verbindungen und verfahren zu ihrer herstellung |
| DE4011695 | 1990-04-11 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI911700A0 FI911700A0 (fi) | 1991-04-09 |
| FI911700A7 FI911700A7 (fi) | 1991-10-12 |
| FI101377B1 FI101377B1 (fi) | 1998-06-15 |
| FI101377B true FI101377B (fi) | 1998-06-15 |
Family
ID=6404197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI911700A FI101377B (fi) | 1990-04-11 | 1991-04-09 | Menetelmä N-alkyloitujen 1,4-dihydropyridiiniyhdisteiden valmistamisek si |
Country Status (18)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4342196A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Neue 4-Phenyl-substituierte 1,4-Dihydropyridine |
| DE4125271A1 (de) * | 1991-07-31 | 1993-02-11 | Bayer Ag | Neue n-alkylierte 1,4-dihydropyridindicarbonsaeureester |
| US5310917A (en) * | 1991-09-13 | 1994-05-10 | Merck & Co., Inc. | Process for the preparation of 4-substituted-1,4-dihydropydrines |
| WO1993006082A1 (en) * | 1991-09-13 | 1993-04-01 | Merck & Co., Inc. | Process for the preparation of 4-substituted-1,4-dihydropyridines |
| DE4133257A1 (de) * | 1991-10-08 | 1993-04-15 | Bayer Ag | N-methyl-nimodipin, verfahren zu seiner herstellung und seine verwendung als zerebraltherapeutikum |
| DE4200714A1 (de) * | 1992-01-14 | 1993-07-15 | Bayer Ag | Spezieller 1,4-dihydropyridin-3,5-dicarbonsaeureester, verfahren zu seiner herstellung und seine pharmazeutische verwendung |
| DE4223867A1 (de) * | 1992-07-20 | 1994-01-27 | Bayer Ag | Spezieller 1,4-Dihydropyridin-3,5-dicarbonsäureester, Verfahren zu seiner Herstellung und seine pharmazeutische Verwendung |
| DE4313691A1 (de) * | 1993-04-27 | 1994-11-03 | Bayer Ag | 2,6-Disubstituierte 4-Chinolyl-dihydropyridine |
| DE4313697A1 (de) * | 1993-04-27 | 1994-11-03 | Bayer Ag | Chinolyl-dihydropyridinester, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln |
| DE4313692A1 (de) * | 1993-04-27 | 1994-11-03 | Bayer Ag | 3-Chinolyl substituierte Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln |
| DE4328884A1 (de) * | 1993-08-27 | 1995-03-02 | Bayer Ag | Verwendung von N-alkylierten 1,4-Dihydropyridincarbonsäureestern als Arzneimittel |
| EE03192B1 (et) * | 1993-12-10 | 1999-06-15 | Bayer Aktiengesellschaft | Isopropüül-(2-metoksüetüül)-4-(2-kloro-3-tsüanofenüül)-1,4-dihüdro-2,6-dimetüülpüri diin-3,5-dikarboksülaat, selle enantiomeerid ja vaheühend, meetodid nimetatud ühendite valmistamiseks ja kasutamine |
| EP0657432B1 (de) * | 1993-12-10 | 2003-03-12 | Bayer Ag | Phenyl-substituierte 1,4-Dihydropyridine mit cerebraler Aktivität |
| DE4430094A1 (de) | 1994-08-25 | 1996-02-29 | Bayer Ag | Verwendung von 3,5-Dicarbonsäureester-1,4-Dihydropyridinen als Arzneimittel |
| DE19638570A1 (de) * | 1996-09-20 | 1998-03-26 | Bayer Ag | Wirkstoffhaltige thermoplastische Polyurethane |
| CA2470813A1 (en) * | 2001-12-20 | 2003-07-03 | Bayer Healthcare Ag | 1,4-dihydro-1,4-diphenylpyridine derivatives |
| US8420790B2 (en) | 2009-10-30 | 2013-04-16 | Reliable Biopharmaceutical Corporation | Efficient and scalable process for the manufacture of Fondaparinux sodium |
| CN110606822A (zh) | 2011-11-24 | 2019-12-24 | 里克特吉迪翁公司 | 具有hsp调节活性的1,4-二氢吡啶衍生物 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US3883543A (en) * | 1969-05-10 | 1975-05-13 | Bayer Ag | N-alkyl-1,4-dihydropyridines |
| DE1963188A1 (de) * | 1969-12-17 | 1971-06-24 | Bayer Ag | Neue Cyanphenyl-1,4-dihydropyridinderivate |
| CH550189A (de) * | 1971-01-08 | 1974-06-14 | Ciba Geigy Ag | Verfahren zur herstellung von neuen dibenzo (b,f) thiepincarbonsaeuren. |
| 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 |
| DE2210667A1 (de) * | 1972-03-06 | 1973-09-20 | Bayer Ag | Kondensiert aromatisch substituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2228377A1 (de) * | 1972-06-10 | 1974-01-03 | Bayer Ag | Dihydropyridin-carbonsaeureamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| CH569043A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-01-23 | 1975-11-14 | Ciba Geigy Ag | |
| US3956341A (en) * | 1974-02-21 | 1976-05-11 | Smithkline Corporation | 1,3,5-Tricarbo-1,4-dihydropyridines |
| SU798099A1 (ru) * | 1978-03-06 | 1981-01-23 | Ордена Трудового Красного Знамениинститут Органического Синтезаан Латвийской Ccp | 1-Бензил-2,6-диметил-4-о-или-M-НиТРОфЕНил-3,5-диэТОКСиКАРбОНил- 1,4-дигидРОпиРидиНы, пРО Вл ющиЕКОРОНАРОдилАТиРующую АКТиВНОСТь |
| DE3587851D1 (de) * | 1984-09-28 | 1994-07-21 | Byk Gulden Lomberg Chem Fab | Neue Diarylverbindungen. |
| US4975440A (en) * | 1984-09-28 | 1990-12-04 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Optically-active 1,4-dihydropyridine |
| US4780538A (en) * | 1986-02-12 | 1988-10-25 | Merck & Co., Inc. | Process for 1,4-dihydropyridine compounds using a titanamine catalyst |
| GB8616047D0 (en) * | 1986-07-01 | 1986-08-06 | Sandoz Ltd | A 1 4-dihydropyridine derivatives |
| GR1002248B (en) * | 1988-03-08 | 1996-04-23 | Egyt Gyogyszervegyeszeti Gyar | 1,4-dihydropyridine derivatives preparation method |
-
1990
- 1990-04-11 DE DE4011695A patent/DE4011695A1/de not_active Withdrawn
-
1991
- 1991-03-30 ES ES91105115T patent/ES2063998T3/es not_active Expired - Lifetime
- 1991-03-30 DK DK91105115.9T patent/DK0451654T3/da active
- 1991-03-30 DE DE59102788T patent/DE59102788D1/de not_active Expired - Fee Related
- 1991-03-30 EP EP91105115A patent/EP0451654B1/de not_active Expired - Lifetime
- 1991-03-30 AT AT91105115T patent/ATE111079T1/de active
- 1991-04-04 US US07/680,454 patent/US5234935A/en not_active Expired - Fee Related
- 1991-04-08 IL IL9779691A patent/IL97796A/en not_active IP Right Cessation
- 1991-04-08 NZ NZ237722A patent/NZ237722A/en unknown
- 1991-04-08 JP JP3101762A patent/JP3012352B2/ja not_active Expired - Lifetime
- 1991-04-08 CA CA002040062A patent/CA2040062A1/en not_active Abandoned
- 1991-04-09 AU AU74253/91A patent/AU642992B2/en not_active Ceased
- 1991-04-09 PT PT97300A patent/PT97300B/pt not_active IP Right Cessation
- 1991-04-09 FI FI911700A patent/FI101377B/fi active
- 1991-04-10 ZA ZA912652A patent/ZA912652B/xx unknown
- 1991-04-10 KR KR1019910005710A patent/KR0180741B1/ko not_active Expired - Fee Related
- 1991-04-10 IE IE120091A patent/IE64452B1/en not_active IP Right Cessation
- 1991-04-10 TW TW080102712A patent/TW197423B/zh active
- 1991-04-11 HU HU911184A patent/HUT59905A/hu unknown
-
1993
- 1993-05-21 US US08/065,503 patent/US5432185A/en not_active Expired - Fee Related
-
1995
- 1995-06-22 HU HU95P/P00334P patent/HU211313A9/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5234935A (en) | 1993-08-10 |
| PT97300B (pt) | 1998-10-30 |
| ES2063998T3 (es) | 1995-01-16 |
| IL97796A (en) | 1995-03-15 |
| AU7425391A (en) | 1991-10-17 |
| DK0451654T3 (da) | 1995-02-13 |
| FI101377B1 (fi) | 1998-06-15 |
| HU211313A9 (en) | 1995-11-28 |
| ZA912652B (en) | 1992-01-29 |
| IE64452B1 (en) | 1995-08-09 |
| PT97300A (pt) | 1992-01-31 |
| JP3012352B2 (ja) | 2000-02-21 |
| EP0451654A2 (de) | 1991-10-16 |
| CA2040062A1 (en) | 1991-10-12 |
| DE59102788D1 (de) | 1994-10-13 |
| IE911200A1 (en) | 1991-10-23 |
| KR0180741B1 (ko) | 1999-03-20 |
| TW197423B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-01-01 |
| HU911184D0 (en) | 1991-10-28 |
| EP0451654A3 (en) | 1992-07-08 |
| DE4011695A1 (de) | 1991-10-17 |
| IL97796A0 (en) | 1992-06-21 |
| NZ237722A (en) | 1995-10-26 |
| ATE111079T1 (de) | 1994-09-15 |
| HUT59905A (en) | 1992-07-28 |
| JPH04234847A (ja) | 1992-08-24 |
| US5432185A (en) | 1995-07-11 |
| EP0451654B1 (de) | 1994-09-07 |
| FI911700A0 (fi) | 1991-04-09 |
| AU642992B2 (en) | 1993-11-04 |
| KR910018025A (ko) | 1991-11-30 |
| FI911700A7 (fi) | 1991-10-12 |
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