NO309125B1 - Anvendelse av 1-alkyl-5-acyl-1,4-dihydropyridiner for fremstilling av legemidler som har en selektiv modulerende virkning på kaliumkanaler, samt utvalgte nye dihydropyridiner - Google Patents
Anvendelse av 1-alkyl-5-acyl-1,4-dihydropyridiner for fremstilling av legemidler som har en selektiv modulerende virkning på kaliumkanaler, samt utvalgte nye dihydropyridiner Download PDFInfo
- Publication number
- NO309125B1 NO309125B1 NO955104A NO955104A NO309125B1 NO 309125 B1 NO309125 B1 NO 309125B1 NO 955104 A NO955104 A NO 955104A NO 955104 A NO955104 A NO 955104A NO 309125 B1 NO309125 B1 NO 309125B1
- Authority
- NO
- Norway
- Prior art keywords
- acetyl
- trimethyl
- carbon atoms
- stands
- alkyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims abstract description 10
- 102000004257 Potassium Channel Human genes 0.000 title claims abstract description 7
- 108020001213 potassium channel Proteins 0.000 title claims abstract description 7
- 229940079593 drug Drugs 0.000 title claims description 9
- 230000003804 effect on potassium Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- -1 4-chloro-3-trifluoromethylphenyl Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 6
- 229940126601 medicinal product Drugs 0.000 claims 2
- BKZAJMPKXZAUND-UHFFFAOYSA-N 1-[5-acetyl-1,2,6-trimethyl-4-(2,3,5-trichlorophenyl)-4h-pyridin-3-yl]ethanone Chemical compound CC(=O)C1=C(C)N(C)C(C)=C(C(C)=O)C1C1=CC(Cl)=CC(Cl)=C1Cl BKZAJMPKXZAUND-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 abstract 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 2
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 abstract 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 abstract 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 239000012442 inert solvent Substances 0.000 description 3
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- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 102000005702 Calcium-Activated Potassium Channels Human genes 0.000 description 2
- 108010045489 Calcium-Activated Potassium Channels Proteins 0.000 description 2
- 108091006146 Channels Proteins 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
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- 230000028327 secretion Effects 0.000 description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- OSLAYKKXCYSJSF-ARJAWSKDSA-N (Z)-4-aminopent-3-en-2-one Chemical compound C\C(N)=C\C(C)=O OSLAYKKXCYSJSF-ARJAWSKDSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- KPYBNSGFXQGVOM-UHFFFAOYSA-N 1-[5-acetyl-1,2,6-trimethyl-4-(2,4,5-trichlorophenyl)-4h-pyridin-3-yl]ethanone Chemical compound CC(=O)C1=C(C)N(C)C(C)=C(C(C)=O)C1C1=CC(Cl)=C(Cl)C=C1Cl KPYBNSGFXQGVOM-UHFFFAOYSA-N 0.000 description 1
- LXQRQVUSDOKVLD-UHFFFAOYSA-N 2,4,5-trichlorobenzaldehyde Chemical compound ClC1=CC(Cl)=C(C=O)C=C1Cl LXQRQVUSDOKVLD-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- PGHMRUGBZOYCAA-ADZNBVRBSA-N ionomycin Chemical compound O1[C@H](C[C@H](O)[C@H](C)[C@H](O)[C@H](C)/C=C/C[C@@H](C)C[C@@H](C)C(/O)=C/C(=O)[C@@H](C)C[C@@H](C)C[C@@H](CCC(O)=O)C)CC[C@@]1(C)[C@@H]1O[C@](C)([C@@H](C)O)CC1 PGHMRUGBZOYCAA-ADZNBVRBSA-N 0.000 description 1
- PGHMRUGBZOYCAA-UHFFFAOYSA-N ionomycin Natural products O1C(CC(O)C(C)C(O)C(C)C=CCC(C)CC(C)C(O)=CC(=O)C(C)CC(C)CC(CCC(O)=O)C)CCC1(C)C1OC(C)(C(C)O)CC1 PGHMRUGBZOYCAA-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- MXXNRLBDAUTKLW-UHFFFAOYSA-N methyl 5-acetyl-4-(4-chlorophenyl)-1,2,6-trimethyl-4h-pyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)N(C)C(C)=C(C(C)=O)C1C1=CC=C(Cl)C=C1 MXXNRLBDAUTKLW-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000955 neuroendocrine Effects 0.000 description 1
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- 239000002858 neurotransmitter agent Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- 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
-
- 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
- A61K31/4422—1,4-Dihydropyridines, e.g. nifedipine, nicardipine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4444864A DE4444864A1 (de) | 1994-12-16 | 1994-12-16 | Verwendung von 5-Acyl-1,4-dihydropyridinen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO955104D0 NO955104D0 (no) | 1995-12-15 |
| NO955104L NO955104L (no) | 1996-06-17 |
| NO309125B1 true NO309125B1 (no) | 2000-12-18 |
Family
ID=6535989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO955104A NO309125B1 (no) | 1994-12-16 | 1995-12-15 | Anvendelse av 1-alkyl-5-acyl-1,4-dihydropyridiner for fremstilling av legemidler som har en selektiv modulerende virkning på kaliumkanaler, samt utvalgte nye dihydropyridiner |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US5646166A (el) |
| EP (1) | EP0717036B1 (el) |
| JP (1) | JPH08239364A (el) |
| KR (1) | KR960022464A (el) |
| CN (1) | CN1130505A (el) |
| AT (1) | ATE177735T1 (el) |
| AU (1) | AU704466B2 (el) |
| CA (1) | CA2165130A1 (el) |
| CZ (1) | CZ332995A3 (el) |
| DE (2) | DE4444864A1 (el) |
| DK (1) | DK0717036T3 (el) |
| EE (1) | EE9500075A (el) |
| ES (1) | ES2130506T3 (el) |
| FI (1) | FI956015A (el) |
| GR (1) | GR3030319T3 (el) |
| HU (1) | HUT74185A (el) |
| IL (1) | IL116387A (el) |
| NO (1) | NO309125B1 (el) |
| NZ (1) | NZ280662A (el) |
| PL (1) | PL311845A1 (el) |
| RU (1) | RU2158259C2 (el) |
| SI (1) | SI0717036T1 (el) |
| SK (1) | SK158195A3 (el) |
| TW (1) | TW381023B (el) |
| ZA (1) | ZA9510693B (el) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2348165A1 (en) * | 1998-10-28 | 2000-05-04 | Abbott Laboratories | Dihydropyridine compounds and methods of use |
| EP1377580B1 (en) * | 2001-01-30 | 2006-09-27 | Eli Lilly And Company | Benzenesulfonic acid indol-5-yl esters as antagonists of the 5-ht6 receptor |
| US20030045449A1 (en) * | 2001-08-15 | 2003-03-06 | Pfizer, Inc. | Pharmaceutical combinations for the treatment of neurodegenerative diseases |
| US20050075359A1 (en) * | 2003-03-14 | 2005-04-07 | Rikako Kono | Large conductance calcium-activated K channel opener |
| AU2006203819A1 (en) * | 2005-01-07 | 2006-07-13 | Roskamp Research Llc | Compounds for inhibiting beta-amyloid production and methods of identifying the compounds |
| WO2013076516A1 (en) * | 2011-11-24 | 2013-05-30 | Lipidart Kutató Fejlesztő És Tanácsadó Kft. | 1,4- dihydropyridine derivatives with hsp modulating activity |
| CN103420900B (zh) * | 2012-05-22 | 2015-06-03 | 中国科学院大连化学物理研究所 | 一种制备卤代-1,2-二氢吡啶的方法 |
| CN103420901B (zh) * | 2012-05-22 | 2015-06-17 | 中国科学院大连化学物理研究所 | 一种制备1,2-二氢吡啶衍生物的方法 |
| CN103804286B (zh) * | 2012-11-06 | 2016-07-06 | 中国科学院大连化学物理研究所 | 一种由3-氮杂-1,5-烯炔制备吡啶衍生物的方法 |
| CN103804283B (zh) * | 2012-11-06 | 2016-04-20 | 中国科学院大连化学物理研究所 | 一种制备1,2-二氢吡啶衍生物的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966948A (en) | 1970-01-24 | 1976-06-29 | Bayer Aktiengesellschaft | Spasmolytic, vaso-dilating and anti-hypertensive compositions and methods |
| DE2018739A1 (en) | 1970-04-18 | 1971-10-28 | Farbenfabriken Bayer Ag, 5090 Leverkusen | 1,4-dihydro-3,5-diacyl-4-arylpyridines,coronary active |
| DE2018738A1 (en) | 1970-04-18 | 1971-10-28 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Hydrogenated pyridines, quinolines andacridi |
| GB1430961A (en) * | 1972-01-22 | 1976-04-07 | Yamanouchi Pharma Co Ltd | 1-substituted-1,4-dihyddrypyridine derivatives |
| FR2649395B1 (fr) * | 1989-07-04 | 1992-11-06 | Adir | Nouveau derive de la dihydro-1,4 pyridine denomme (-) i1(((amino-2 ethoxy)-2 ethoxy) methyli1) -2 (dichloro-2,3 phenyl)-4 ethoxycarbonyl-3 methoxycarbonyl-5 methyl-6 dihydro-1,4 pyridine, son procede de preparation et les compositions qui le contiennent |
| US5446057A (en) * | 1993-09-24 | 1995-08-29 | Warner-Lambert Company | Substituted tetrahydropyridine and piperidine carboxylic acids as muscarinic antagonists |
| JP3709997B2 (ja) * | 1994-03-29 | 2005-10-26 | 日東電工株式会社 | 耐熱性ネガ型フォトレジスト組成物および感光性基材、ならびにネガ型パターン形成方法 |
-
1994
- 1994-12-16 DE DE4444864A patent/DE4444864A1/de not_active Withdrawn
-
1995
- 1995-11-24 TW TW084112525A patent/TW381023B/zh not_active IP Right Cessation
- 1995-12-04 ES ES95119053T patent/ES2130506T3/es not_active Expired - Lifetime
- 1995-12-04 EP EP95119053A patent/EP0717036B1/de not_active Expired - Lifetime
- 1995-12-04 DK DK95119053T patent/DK0717036T3/da active
- 1995-12-04 DE DE59505373T patent/DE59505373D1/de not_active Expired - Fee Related
- 1995-12-04 AT AT95119053T patent/ATE177735T1/de not_active IP Right Cessation
- 1995-12-04 SI SI9530214T patent/SI0717036T1/xx unknown
- 1995-12-07 AU AU40293/95A patent/AU704466B2/en not_active Ceased
- 1995-12-08 US US08/569,438 patent/US5646166A/en not_active Expired - Fee Related
- 1995-12-13 CA CA002165130A patent/CA2165130A1/en not_active Abandoned
- 1995-12-13 NZ NZ280662A patent/NZ280662A/en unknown
- 1995-12-13 JP JP7346237A patent/JPH08239364A/ja active Pending
- 1995-12-14 IL IL11638795A patent/IL116387A/xx not_active IP Right Cessation
- 1995-12-14 PL PL95311845A patent/PL311845A1/xx unknown
- 1995-12-14 FI FI956015A patent/FI956015A/fi unknown
- 1995-12-15 KR KR1019950050397A patent/KR960022464A/ko not_active Application Discontinuation
- 1995-12-15 HU HU9503592A patent/HUT74185A/hu unknown
- 1995-12-15 ZA ZA9510693A patent/ZA9510693B/xx unknown
- 1995-12-15 SK SK1581-95A patent/SK158195A3/sk unknown
- 1995-12-15 EE EE9500075A patent/EE9500075A/xx unknown
- 1995-12-15 RU RU95121070/04A patent/RU2158259C2/ru active
- 1995-12-15 CZ CZ953329A patent/CZ332995A3/cs unknown
- 1995-12-15 NO NO955104A patent/NO309125B1/no not_active IP Right Cessation
- 1995-12-15 CN CN95121330A patent/CN1130505A/zh active Pending
-
1997
- 1997-02-11 US US08/798,255 patent/US5942526A/en not_active Expired - Fee Related
-
1999
- 1999-05-27 GR GR990401406T patent/GR3030319T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2130506T3 (es) | 1999-07-01 |
| SI0717036T1 (en) | 1999-06-30 |
| CA2165130A1 (en) | 1996-06-17 |
| KR960022464A (ko) | 1996-07-18 |
| PL311845A1 (en) | 1996-06-24 |
| CZ332995A3 (en) | 1996-07-17 |
| US5646166A (en) | 1997-07-08 |
| NO955104D0 (no) | 1995-12-15 |
| DE4444864A1 (de) | 1996-06-20 |
| DE59505373D1 (de) | 1999-04-22 |
| GR3030319T3 (en) | 1999-09-30 |
| FI956015A (fi) | 1996-06-17 |
| HU9503592D0 (en) | 1996-02-28 |
| AU704466B2 (en) | 1999-04-22 |
| IL116387A (en) | 2000-11-21 |
| NZ280662A (en) | 1997-02-24 |
| EE9500075A (et) | 1996-06-17 |
| IL116387A0 (en) | 1996-03-31 |
| JPH08239364A (ja) | 1996-09-17 |
| AU4029395A (en) | 1996-06-27 |
| CN1130505A (zh) | 1996-09-11 |
| US5942526A (en) | 1999-08-24 |
| EP0717036A1 (de) | 1996-06-19 |
| DK0717036T3 (da) | 1999-10-11 |
| ZA9510693B (en) | 1996-07-03 |
| SK158195A3 (en) | 1996-09-04 |
| RU2158259C2 (ru) | 2000-10-27 |
| HUT74185A (en) | 1996-11-28 |
| NO955104L (no) | 1996-06-17 |
| ATE177735T1 (de) | 1999-04-15 |
| FI956015A0 (fi) | 1995-12-14 |
| TW381023B (en) | 2000-02-01 |
| EP0717036B1 (de) | 1999-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN JUNE 2002 |