FI89166C - Foerfarande foer framstaellning av terapeutiskt aktiva heterocykliska foereningar - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva heterocykliska foereningar Download PDFInfo
- Publication number
- FI89166C FI89166C FI853103A FI853103A FI89166C FI 89166 C FI89166 C FI 89166C FI 853103 A FI853103 A FI 853103A FI 853103 A FI853103 A FI 853103A FI 89166 C FI89166 C FI 89166C
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- Finland
- Prior art keywords
- formula
- compound
- methyl
- defined above
- dihydro
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- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 88
- -1 sulfonyloxy group Chemical group 0.000 claims description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- YLEGUTIKJYHCET-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound N1C(C)=C(C(O)=O)C(C=2C=C(C=CC=2)[N+]([O-])=O)C(C(O)=O)=C1CN1C=CN=C1 YLEGUTIKJYHCET-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 2
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 2
- BTYZSLAEGMMHGN-UHFFFAOYSA-N 2-methyl-4-(3-nitrophenyl)-6-(pyridin-3-yloxymethyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound N1C(C)=C(C(O)=O)C(C=2C=C(C=CC=2)[N+]([O-])=O)C(C(O)=O)=C1COC1=CC=CN=C1 BTYZSLAEGMMHGN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 101100232295 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) GLK1 gene Proteins 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- VVHYPAOOAMQMFV-UHFFFAOYSA-N dimethyl 4-(2,3-dichlorophenyl)-2-(2-imidazol-1-ylethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(NC(=C(C1C1=C(C(=CC=C1)Cl)Cl)C(=O)OC)C)CCN1C=NC=C1 VVHYPAOOAMQMFV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- SMJWHUFENZBYFF-UHFFFAOYSA-N COC(=O)C=1C(C(=C(NC1C)CC=1NC=CN1)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-] Chemical compound COC(=O)C=1C(C(=C(NC1C)CC=1NC=CN1)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-] SMJWHUFENZBYFF-UHFFFAOYSA-N 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 25
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- 238000004220 aggregation Methods 0.000 description 5
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
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- PZSKEXIHJQBKRF-UHFFFAOYSA-N diethyl 2-(2-imidazol-1-ylethyl)-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C=1C(C=2C(=CC=CC=2)[N+]([O-])=O)C(C(=O)OCC)=C(C)NC=1CCN1C=CN=C1 PZSKEXIHJQBKRF-UHFFFAOYSA-N 0.000 description 1
- HHLKLVCAVMNNMT-UHFFFAOYSA-N diethyl 2-[2-(dimethylamino)ethyl]-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(CCN(C)C)=C(C(=O)OCC)C1C1=CC=CC([N+]([O-])=O)=C1 HHLKLVCAVMNNMT-UHFFFAOYSA-N 0.000 description 1
- PGGQCHVPWSXPSI-UHFFFAOYSA-N diethyl pyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=CN=CC(C(=O)OCC)=C1 PGGQCHVPWSXPSI-UHFFFAOYSA-N 0.000 description 1
- FUXVZXSCPAIJCJ-UHFFFAOYSA-N dimethyl 1,2,6-trimethyl-4-(3-nitrophenyl)-4h-pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)N(C)C(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 FUXVZXSCPAIJCJ-UHFFFAOYSA-N 0.000 description 1
- MWULSRFCFJZYOY-UHFFFAOYSA-N dimethyl 2-(1h-imidazol-2-ylmethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C=1C(C=2C=C(C=CC=2)[N+]([O-])=O)C(C(=O)OC)=C(C)NC=1CC1=NC=CN1 MWULSRFCFJZYOY-UHFFFAOYSA-N 0.000 description 1
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- IADJFPRMDZEXJS-UHFFFAOYSA-N dimethyl 2-[2-(benzimidazol-1-yl)ethyl]-4-(2,3-dichlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(CCN2C3=CC=CC=C3N=C2)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl IADJFPRMDZEXJS-UHFFFAOYSA-N 0.000 description 1
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- GJWDEVSJBHKJAL-UHFFFAOYSA-N dimethyl 4-(2,3-dichlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)N=C(C)C(C(=O)OC)=C1C1=CC=CC(Cl)=C1Cl GJWDEVSJBHKJAL-UHFFFAOYSA-N 0.000 description 1
- LCVNWZGBDMRKDN-UHFFFAOYSA-N dimethyl 4-(2,3-dichlorophenyl)-2-(1h-imidazol-2-ylmethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C=1C(C=2C(=C(Cl)C=CC=2)Cl)C(C(=O)OC)=C(C)NC=1CC1=NC=CN1 LCVNWZGBDMRKDN-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
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- YOPMSDPIOQUWFE-XYOKQWHBSA-N ethyl (2e)-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(\C(C)=O)=C\C1=CC=CC([N+]([O-])=O)=C1 YOPMSDPIOQUWFE-XYOKQWHBSA-N 0.000 description 1
- YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- LYUBYLJQOZIBQB-UHFFFAOYSA-N methyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate Chemical compound COC(=O)C(C(C)=O)=CC1=CC=CC([N+]([O-])=O)=C1 LYUBYLJQOZIBQB-UHFFFAOYSA-N 0.000 description 1
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- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000011587 new zealand white rabbit Methods 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 239000008279 sol Substances 0.000 description 1
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- 239000008174 sterile solution Substances 0.000 description 1
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- 239000011550 stock solution Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 210000003462 vein Anatomy 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/12—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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848421039A GB8421039D0 (en) | 1984-08-17 | 1984-08-17 | Heterocyclic compounds |
| GB8421039 | 1984-08-17 | ||
| GB8515751 | 1985-06-21 | ||
| GB858515751A GB8515751D0 (en) | 1985-06-21 | 1985-06-21 | Heterocyclic compounds |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI853103A0 FI853103A0 (fi) | 1985-08-13 |
| FI853103L FI853103L (fi) | 1986-02-18 |
| FI89166B FI89166B (fi) | 1993-05-14 |
| FI89166C true FI89166C (fi) | 1993-08-25 |
Family
ID=26288137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI853103A FI89166C (fi) | 1984-08-17 | 1985-08-13 | Foerfarande foer framstaellning av terapeutiskt aktiva heterocykliska foereningar |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5068337A (en:Method) |
| EP (1) | EP0172029B1 (en:Method) |
| JP (1) | JPH0680053B2 (en:Method) |
| KR (1) | KR930000167B1 (en:Method) |
| AR (1) | AR241417A1 (en:Method) |
| AT (1) | ATE61055T1 (en:Method) |
| AU (1) | AU587388B2 (en:Method) |
| CA (1) | CA1310011C (en:Method) |
| CZ (1) | CZ279473B6 (en:Method) |
| DE (1) | DE3581858D1 (en:Method) |
| DK (1) | DK374185A (en:Method) |
| ES (1) | ES8604564A1 (en:Method) |
| FI (1) | FI89166C (en:Method) |
| GB (1) | GB2168969B (en:Method) |
| GR (1) | GR851819B (en:Method) |
| HU (1) | HU194868B (en:Method) |
| IE (1) | IE58706B1 (en:Method) |
| IL (1) | IL75943A (en:Method) |
| MY (1) | MY101736A (en:Method) |
| NZ (1) | NZ212956A (en:Method) |
| PH (1) | PH26049A (en:Method) |
| PT (1) | PT80956B (en:Method) |
| SU (1) | SU1486059A3 (en:Method) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1267416A (en) * | 1985-06-17 | 1990-04-03 | Ila Sircar | 1,4-dihydropyridine derivatives useful for the treatment of cardiovascular disorders |
| IT1204421B (it) * | 1986-06-27 | 1989-03-01 | Boehringer Biochemia Srl | 2-(aminoalchiltio)metil-1,4-diidropiridine,un metodo per la loro preparazione e composizioni farmaceutiche che le contengono |
| EP0225175A3 (en) * | 1985-11-28 | 1988-12-28 | FISONS plc | Dihydropyridine derivatives, processes for their preparation and pharmaceutical compositions thereof |
| GB8602518D0 (en) * | 1986-02-01 | 1986-03-05 | Wyeth John & Brother Ltd | 1 4-dihydropyridines |
| DE3617976A1 (de) * | 1986-05-28 | 1988-01-14 | Alter Sa | 1,4-dihydropyridin, verfahren zu dessen herstellung und dessen verwendung in antithrombotischen medikamenten |
| FR2602231B1 (fr) * | 1986-08-04 | 1988-10-28 | Adir | Nouveaux derives de la dihydro-1,4 pyridine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| WO1988005043A1 (en) * | 1986-12-24 | 1988-07-14 | Boehringer Biochemia Robin S.P.A. | New aralkyl-1,4-dihydropyridines, a method for their preparation and pharmaceutical compositions containing them |
| GB8729471D0 (en) * | 1987-12-17 | 1988-02-03 | Wyeth John & Brother Ltd | New crystal form |
| JPH0286981A (ja) * | 1988-09-22 | 1990-03-27 | Aisin Seiki Co Ltd | ロータリ圧縮機 |
| US5616591A (en) * | 1992-03-27 | 1997-04-01 | E.R. Squibb & Sons, Inc. | Indole- and benzimidazole-substituted quinoline derivatives |
| DE4233601A1 (de) * | 1992-10-06 | 1994-04-07 | Bayer Ag | 3-substituierte Chinolin-5-carbonsäuren |
| EP0974663A1 (en) * | 1993-06-25 | 2000-01-26 | Smithkline Beecham Plc | Lipoprotein associated phospholipase A2, inhibitors thereof and use of same in diagnosis and therapy |
| KR100510854B1 (ko) * | 1996-05-01 | 2006-05-12 | 오르토-맥네일 파마슈티칼, 인코퍼레이티드 | 혈전성질환의치료를위한피롤리딘,피페리딘및헥사하이드로아제핀의카르복사미드유도체 |
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| BR0010349B1 (pt) * | 1999-05-07 | 2011-10-04 | derivados de ácido propanóico que inibem a ligação de integrinas aos seus receptores. | |
| DE60112305T2 (de) * | 2000-12-29 | 2006-05-24 | Pfizer Ltd., Sandwich | Verfahren zur herstellung amlodipinmaleat |
| CA2433772C (en) * | 2001-02-14 | 2008-10-07 | Warner-Lambert Company Llc | Pyrimidine matrix metalloproteinase inhibitors |
| US6566359B1 (en) | 2002-05-20 | 2003-05-20 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | 2,4,6-trimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid esters as neuroprotective drugs |
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| GB1552911A (en) * | 1975-07-02 | 1979-09-19 | Fujisawa Pharmaceutical Co | 1,4 dihydropyridine derivatives and the preparation thereof |
| DE2639257A1 (de) * | 1976-09-01 | 1978-03-02 | Bayer Ag | Aminoalkylidenamino-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2658183A1 (de) * | 1976-12-22 | 1978-07-06 | Bayer Ag | In 2-position substituierte 1,4- dihydropyridin-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4177278A (en) * | 1977-04-05 | 1979-12-04 | Bayer Aktiengesellschaft | 2-Alkyleneaminodihydropyridines compounds, their production and their medicinal use |
| DE2738153A1 (de) * | 1977-08-24 | 1979-03-08 | Bayer Ag | 2-pyridyl-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4307103A (en) * | 1978-09-08 | 1981-12-22 | Fujisawa Pharmaceutical Co., Ltd. | Dihydropyridine derivative, processes for preparation thereof and pharmaceutical composition comprising the same |
| JPS5547656A (en) * | 1978-09-29 | 1980-04-04 | Dainippon Pharmaceut Co Ltd | 2-(2-substituted aminoethyl)-1,4-dihydropyridine derivative and its derivative |
| DE2844595A1 (de) * | 1978-10-13 | 1980-04-30 | Bayer Ag | Acylaminodihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| CS228917B2 (en) * | 1981-03-14 | 1984-05-14 | Pfizer | Method of preparing substituted derivatives of 1,4-dihydropyridine |
| SE8105230L (sv) * | 1981-09-03 | 1983-03-04 | Haessle Ab | Nya dihydropyridiner |
| DE3269219D1 (en) * | 1981-11-17 | 1986-03-27 | Fisons Plc | Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals |
| DE3207982A1 (de) * | 1982-03-05 | 1983-09-08 | Bayer Ag, 5090 Leverkusen | Neue 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihrer verwendung in arzneimitteln |
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| WO1983003249A1 (en) * | 1982-03-17 | 1983-09-29 | Yoshitomi Pharmaceutical | 1,4-dihydropyridine-3,5-dicarboxylate derivatives |
| DE3363743D1 (en) * | 1982-07-22 | 1986-07-03 | Pfizer Ltd | Dihydropyridine anti-ischaemic and antihypertensive agents |
| PH19166A (en) * | 1982-09-04 | 1986-01-16 | Pfizer | Dihydropyridined,pharmaceutical compositions and method of use |
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| US4515799A (en) * | 1983-02-02 | 1985-05-07 | Pfizer Inc. | Dihydropyridine anti-ischaemic and antihypertensive agents |
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| GB8414518D0 (en) * | 1984-06-07 | 1984-07-11 | Pfizer Ltd | Therapeutic agents |
-
1985
- 1985-07-23 GR GR851819A patent/GR851819B/el unknown
- 1985-07-24 IE IE186085A patent/IE58706B1/en not_active IP Right Cessation
- 1985-07-26 AR AR85301104A patent/AR241417A1/es active
- 1985-07-29 IL IL75943A patent/IL75943A/xx not_active IP Right Cessation
- 1985-07-31 CA CA000487896A patent/CA1310011C/en not_active Expired - Fee Related
- 1985-08-01 NZ NZ212956A patent/NZ212956A/xx unknown
- 1985-08-02 AU AU45726/85A patent/AU587388B2/en not_active Ceased
- 1985-08-13 FI FI853103A patent/FI89166C/fi not_active IP Right Cessation
- 1985-08-14 PH PH32635A patent/PH26049A/en unknown
- 1985-08-14 PT PT80956A patent/PT80956B/pt not_active IP Right Cessation
- 1985-08-15 CZ CS855922A patent/CZ279473B6/cs unknown
- 1985-08-15 DE DE8585305803T patent/DE3581858D1/de not_active Expired - Fee Related
- 1985-08-15 AT AT85305803T patent/ATE61055T1/de not_active IP Right Cessation
- 1985-08-15 EP EP85305803A patent/EP0172029B1/en not_active Expired - Lifetime
- 1985-08-15 GB GB08520485A patent/GB2168969B/en not_active Expired
- 1985-08-16 JP JP60180894A patent/JPH0680053B2/ja not_active Expired - Lifetime
- 1985-08-16 SU SU853940051A patent/SU1486059A3/ru active
- 1985-08-16 ES ES546189A patent/ES8604564A1/es not_active Expired
- 1985-08-16 HU HU853175A patent/HU194868B/hu not_active IP Right Cessation
- 1985-08-16 KR KR1019850005902A patent/KR930000167B1/ko not_active Expired - Fee Related
- 1985-08-16 DK DK374185A patent/DK374185A/da unknown
-
1986
- 1986-11-13 US US06/930,972 patent/US5068337A/en not_active Expired - Fee Related
-
1987
- 1987-05-18 MY MYPI87000676A patent/MY101736A/en unknown
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Legal Events
| Date | Code | Title | Description |
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| BB | Publication of examined application | ||
| MM | Patent lapsed |
Owner name: JOHN WYETH & BROTHER LIMITED |