FI81100B - Foerfarande foer framstaellning av terapeutiskt aktiva 1,4,5,7-tetrahydrofuro/3,4-b/pyridinderivat. - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva 1,4,5,7-tetrahydrofuro/3,4-b/pyridinderivat. Download PDFInfo
- Publication number
- FI81100B FI81100B FI841153A FI841153A FI81100B FI 81100 B FI81100 B FI 81100B FI 841153 A FI841153 A FI 841153A FI 841153 A FI841153 A FI 841153A FI 81100 B FI81100 B FI 81100B
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- Finland
- Prior art keywords
- formula
- defined above
- group
- carbon atoms
- alkyl
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 44
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- -1 straight-chain Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000002081 enamines Chemical class 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004122 cyclic group Chemical class 0.000 claims description 5
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims description 5
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000006241 alcohol protecting group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims 2
- DEWNXYXWUROCHP-UHFFFAOYSA-N 1,4,5,7-tetrahydrofuro[3,4-b]pyridine Chemical class C1C=CNC2=C1COC2 DEWNXYXWUROCHP-UHFFFAOYSA-N 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
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- 239000001257 hydrogen Substances 0.000 abstract description 6
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- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
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- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 abstract 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
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- 230000008602 contraction Effects 0.000 description 4
- AOKGPWIRRWBVRG-DAXSKMNVSA-N ethyl (z)-4-acetyloxy-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(/N)COC(C)=O AOKGPWIRRWBVRG-DAXSKMNVSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 125000004414 alkyl thio group Chemical group 0.000 description 3
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- 238000001816 cooling Methods 0.000 description 3
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- 210000002837 heart atrium Anatomy 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
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- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
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- 235000019359 magnesium stearate Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
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- 231100000252 nontoxic Toxicity 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical class C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HJCKWIIBFLDPOB-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-oxochromene-8-carbaldehyde Chemical compound ClC1=CC=CC(C=2OC3=C(C=O)C=CC=C3C(=O)C=2)=C1 HJCKWIIBFLDPOB-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WUESBHAZGPHYJE-UHFFFAOYSA-N 4-acetyloxy-3-oxobutanoic acid Chemical compound CC(=O)OCC(=O)CC(O)=O WUESBHAZGPHYJE-UHFFFAOYSA-N 0.000 description 1
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- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
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- 229940126601 medicinal product Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- PISGFYGZIOIJOH-UHFFFAOYSA-N methyl 2-methyl-5-oxo-4-(4-oxo-2-phenylthiochromen-8-yl)-4,7-dihydro-1h-furo[3,4-b]pyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)NC(COC2=O)=C2C1C1=CC=CC(C(C=2)=O)=C1SC=2C1=CC=CC=C1 PISGFYGZIOIJOH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Chemical group 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 150000003892 tartrate salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 229930195735 unsaturated hydrocarbon Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Steroid Compounds (AREA)
Claims (6)
1. Förfarande för framställning av terapeutiskt aktiva 1,4,5,7-tetrahydrofuro^3,4-bjpyridinderivat med 5 formeIn I 0 10 (ΟΧτΙγ Λ Λ R1 I 0 0 R"° TT/ 15 “3 H 20 väri R·*· är en möjligen med halogen substituerad fenyl, en rak-kedjad, cyklisk eller förgrenad alkyl med 1-10 kolatomer, en karboxylsyraalkylester med 1-6 C-atomer i alkylgruppen, en pyridyl- eller en tienylgrupp, 4
25 R är en rakkedjad eller förgrenad alkyl med 1-10 C-atomer, en alkylen med 2-10 C-atomer, en cykloalkyl med 5 eller 6 C-atomer i ringen, en cyklohexylmetylgrupp, en C^_^-alkyl-grupp som kan vara substituerad med en trimetylsilylgrupp, eller med en alkoxigrupp med 1-6 C-atomer, eller med en 30 metylmerkaptogrupp, eller med en bensylgrupp som kan vara substituerad med en metylmerkaptogrupp, ooh X är 0 eller S, samt av dessa föreningars salter, kännetecknat därav, att 28 81 1 00 A) aldehyder med formeln II 0 5 (ρτ\ H 10 vari R* och X har ovan angivna betydelse, omsättes med enaminer med formeln III .•-A CH3/XVx'NH2 20 4 väri R har ovan angivna betydelse, och med ketoner med formeln IV 0
25 A^^OR7 IV Z vari 7 R är en alkylgrupp med 1-6 C-atomer, och Z är halogen 30 eller -O-B, varvid B är en alkoholskyddsgrupp, sAsom -C-CH3, -CH2-0-CH3, ~CH2~~^3^ eller “Si (alkyl) 3 eventuellti närvaro av ett inert, organiskt lösnings-35 medel vid en temperatur mellan 20 och 150°C, och ifall Z är-O-B, avlägsnas skyddsgruppen med lämpliga medel, eller It 29 81 1 00 B) aldehyder med formeln II, väri R* och X har ovan angivna betydelse, omsättes med ketoner med formeln V 0 X 5 r4o CH3\X^ o vari 4 R har ovan angivna betydelse, och med enaminer med 10 formeln VI Λ™· Z VI Ψ 15 7 väri R och Z har ovan angivna betydelse, eventuellt i närvaro av inerta organiska lösningmedel vid en temperatur mellan 20 och 150°C och, dä Z = O-B, väri B har ovan angivna betydelse, avlägsnas skyddsgruppen 20 avslutningsvis med lämpliga medel, eller C) ylidenföreningar med formeln VII 0 (pTjT
25. Y^x^R1 r4o vari CH o 1 4 3
30 R , R och X har ovan angivna betydelse, omsättes med 7 enaminer med formeln VI, vari R och Z har ovan angivna betydelse, eventuellt i närvaro av inerta, organiska lösningsmedel vid en temperatur mellan 20 och 150°C och, dä Z =-0-B, vari B har ovan angivna betydelse, 35 avspjälkes skyddsgruppen avslutningsvis med lämpliga medel, eller 30 81 1 00 D) aldehyder med formeln II, väri R^ och X har ovan angivna betydelse, omsättes med ketoner med formeln V, 4 väri R har ovan angivna betydelse, och med tetronsyra-amider med formeln VIII 5 0 Λ H.H VI11 10 eventuellt i närvaro av inerta, organiska lösningsmedel vid en temperatur mellan 20 och 150°C, eller E) bensylidenföreningar med formeln IX 0 15 (on l^^^COOR7 Z 20 vari 17 0 R , R , X och Z har ovan angivna betydelse, omsättes 4 med enaminer med formeln III, van R har ovan angivna betydelse, eventuellt i närvaro av inerta, organiska lösningsmedel vid en temperatur mellan 20 och 150°C 25 och, det Z =-0-B, väri B har ovan angivna betydelse, avspjälkes skyddsgruppen med lämpliga medel.
2. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att reaktanterna insätts i ekvi-molära mängder. 30
3. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att föreningarna med formeln III, V och VI insättes i ett överskott av upp till 3 mol.
4. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man utför omsättningen vid 35 en temperatur av 30-120°C. 11 31 81100
5. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man utför omsättningen vid det använda lösningsmedlets kokpunkt.
6. Förfarande enligt patentkravet 1, känne-5 tecknat därav, att man framställer 2-metyl-4- (4-oxo-2-fenyl-4H-tiokromen-8-yl)-5-oxo-l,4,5,7-tetra-hydrofuro^3,4-b} pyridin-3-karboxylsyraetylester.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833311003 DE3311003A1 (de) | 1983-03-25 | 1983-03-25 | Chromon- und thiochromonsubstituierte 1,4-dihydropyridinlactone, mehrere verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| DE3311003 | 1983-03-25 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI841153A0 FI841153A0 (fi) | 1984-03-22 |
| FI841153A FI841153A (fi) | 1984-09-26 |
| FI81100B true FI81100B (fi) | 1990-05-31 |
| FI81100C FI81100C (sv) | 1990-09-10 |
Family
ID=6194710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI841153A FI81100C (sv) | 1983-03-25 | 1984-03-22 | Förfarande för framställning av terapeutiskt aktiva 1,4,5,7-tetrahydro furo/3,4-b/pyridinderivat |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4555512A (sv) |
| EP (1) | EP0123095B1 (sv) |
| JP (1) | JPS59193887A (sv) |
| KR (1) | KR920001137B1 (sv) |
| AT (1) | ATE38229T1 (sv) |
| AU (1) | AU564838B2 (sv) |
| CA (1) | CA1211109A (sv) |
| DE (2) | DE3311003A1 (sv) |
| DK (1) | DK158950C (sv) |
| ES (5) | ES8607307A1 (sv) |
| FI (1) | FI81100C (sv) |
| GR (1) | GR81924B (sv) |
| HU (1) | HU189849B (sv) |
| IE (1) | IE57039B1 (sv) |
| IL (1) | IL71314A (sv) |
| NO (1) | NO160659C (sv) |
| NZ (1) | NZ207588A (sv) |
| PH (1) | PH20322A (sv) |
| PT (1) | PT78311B (sv) |
| ZA (1) | ZA842166B (sv) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4011105A1 (de) * | 1990-04-06 | 1991-10-10 | Bayer Ag | Neue 4-chinolyl-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| US5204472A (en) * | 1990-04-06 | 1993-04-20 | Bayer Aktiengesellschaft | Quinoline and isoquinoline intermediates |
| DE4313696A1 (de) * | 1993-04-27 | 1994-11-03 | Bayer Ag | 2-Amino-4-heteroaryl-1,4-dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln |
| CA2538188A1 (en) * | 2003-09-10 | 2005-03-24 | Synta Pharmaceuticals Corp. | Dihydropyridine compounds for treating or preventing metabolic disorders |
| DE102005034267A1 (de) | 2005-07-22 | 2007-01-25 | Bayer Healthcare Ag | 4-Chromenonyl-1,4-dihydropyridine und ihre Verwendung |
| DE102005034264A1 (de) | 2005-07-22 | 2007-02-01 | Bayer Healthcare Ag | 4-Chromenonyl-1,4-dihydropyridincarbonitrile und ihre Verwendung |
| EP2042496A1 (de) | 2007-09-18 | 2009-04-01 | Bayer CropScience AG | Verfahren zur Herstellung von 4-Aminobut-2-enoliden |
| EP2039678A1 (de) | 2007-09-18 | 2009-03-25 | Bayer CropScience AG | Verfahren zum Herstellen von 4-Aminobut-2-enoliden |
| EP2230236A1 (de) | 2009-03-16 | 2010-09-22 | Bayer CropScience AG | Neues Verfahren zur Herstellung von Enaminocarbonyl-Verbindungen |
| EP2230237A1 (de) | 2009-03-16 | 2010-09-22 | Bayer CropScience AG | Neues Verfahren zur Herstellung von Enaminocarbonyl-Verbindungen |
| TW201111370A (en) | 2009-08-18 | 2011-04-01 | Bayer Cropscience Ag | Novel process for the preparation of 4-aminobut-2-enolides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ201395A (en) * | 1981-07-30 | 1987-02-20 | Bayer Ag | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
| DE3269219D1 (en) * | 1981-11-17 | 1986-03-27 | Fisons Plc | Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals |
| DE3315805A1 (de) * | 1983-04-30 | 1984-11-08 | Bayer Ag, 5090 Leverkusen | Wirkstoffzubereitungen |
| DE3339861A1 (de) * | 1983-11-04 | 1985-05-15 | Bayer Ag, 5090 Leverkusen | Arzneizubereitung enthaltend dihydropyridine |
-
1983
- 1983-03-25 DE DE19833311003 patent/DE3311003A1/de not_active Withdrawn
-
1984
- 1984-02-29 DK DK144984A patent/DK158950C/da not_active IP Right Cessation
- 1984-03-12 DE DE8484102659T patent/DE3474824D1/de not_active Expired
- 1984-03-12 EP EP84102659A patent/EP0123095B1/de not_active Expired
- 1984-03-12 AT AT84102659T patent/ATE38229T1/de not_active IP Right Cessation
- 1984-03-13 NO NO840950A patent/NO160659C/no unknown
- 1984-03-14 US US06/589,614 patent/US4555512A/en not_active Expired - Lifetime
- 1984-03-21 ES ES530800A patent/ES8607307A1/es not_active Expired
- 1984-03-22 IL IL71314A patent/IL71314A/xx not_active IP Right Cessation
- 1984-03-22 NZ NZ207588A patent/NZ207588A/en unknown
- 1984-03-22 FI FI841153A patent/FI81100C/sv not_active IP Right Cessation
- 1984-03-23 CA CA000450361A patent/CA1211109A/en not_active Expired
- 1984-03-23 PH PH30431A patent/PH20322A/en unknown
- 1984-03-23 GR GR74196A patent/GR81924B/el unknown
- 1984-03-23 HU HU841175A patent/HU189849B/hu not_active IP Right Cessation
- 1984-03-23 IE IE716/84A patent/IE57039B1/xx unknown
- 1984-03-23 ZA ZA842166A patent/ZA842166B/xx unknown
- 1984-03-23 PT PT78311A patent/PT78311B/pt not_active IP Right Cessation
- 1984-03-24 KR KR1019840001520A patent/KR920001137B1/ko active IP Right Grant
- 1984-03-24 JP JP59057202A patent/JPS59193887A/ja active Granted
- 1984-03-26 AU AU26099/84A patent/AU564838B2/en not_active Ceased
-
1986
- 1986-02-21 ES ES552278A patent/ES8707957A1/es not_active Expired
- 1986-02-21 ES ES552279A patent/ES8707958A1/es not_active Expired
- 1986-02-21 ES ES552280A patent/ES8707959A1/es not_active Expired
- 1986-02-21 ES ES552277A patent/ES8707952A1/es not_active Expired
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