FI75808C - Foerfarande foer framstaellning av terapeutiskt anvaendbara aminopropanoloxipyridinderivat. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara aminopropanoloxipyridinderivat. Download PDFInfo
- Publication number
- FI75808C FI75808C FI821034A FI821034A FI75808C FI 75808 C FI75808 C FI 75808C FI 821034 A FI821034 A FI 821034A FI 821034 A FI821034 A FI 821034A FI 75808 C FI75808 C FI 75808C
- Authority
- FI
- Finland
- Prior art keywords
- compound
- formula
- ether
- preparation
- compounds
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- KVCOOWROABTXDJ-UHFFFAOYSA-N 6-chloropyridin-3-ol Chemical compound OC1=CC=C(Cl)N=C1 KVCOOWROABTXDJ-UHFFFAOYSA-N 0.000 claims description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 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 claims description 2
- 239000007787 solid Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 4
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- GQJZJKJIYYMRLA-UHFFFAOYSA-N 2-chloro-5-[2-(cyclopropylmethoxy)ethoxy]pyridine Chemical compound C1=NC(Cl)=CC=C1OCCOCC1CC1 GQJZJKJIYYMRLA-UHFFFAOYSA-N 0.000 description 2
- -1 2-cyclopropylmethoxyethoxy Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229960001317 isoprenaline Drugs 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- HNOAXSVPMXZKBT-UHFFFAOYSA-N (2-phenyl-3-propan-2-yl-1,3-oxazolidin-5-yl)methanol Chemical compound CC(C)N1CC(CO)OC1C1=CC=CC=C1 HNOAXSVPMXZKBT-UHFFFAOYSA-N 0.000 description 1
- HUIBFXXMYGQSAH-HNNXBMFYSA-N (2s)-1-(tert-butylamino)-3-[5-[2-(cyclopropylmethoxy)ethoxy]pyridin-2-yl]oxypropan-2-ol Chemical compound C1=NC(OC[C@@H](O)CNC(C)(C)C)=CC=C1OCCOCC1CC1 HUIBFXXMYGQSAH-HNNXBMFYSA-N 0.000 description 1
- VUIYJOZPJCIVAA-UHFFFAOYSA-N 1-[5-[2-(cyclopropylmethoxy)ethoxy]pyridin-2-yl]oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=NC(OCC(O)CNC(C)C)=CC=C1OCCOCC1CC1 VUIYJOZPJCIVAA-UHFFFAOYSA-N 0.000 description 1
- FHDRFAXKVIXVIJ-UHFFFAOYSA-N 1-[6-[2-(cyclopropylmethoxy)ethoxy]pyridin-3-yl]oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound N1=CC(OCC(O)CNC(C)C)=CC=C1OCCOCC1CC1 FHDRFAXKVIXVIJ-UHFFFAOYSA-N 0.000 description 1
- CRYSXEGANJJZKJ-UHFFFAOYSA-N 2-(cyclopropylmethoxy)ethanol Chemical compound OCCOCC1CC1 CRYSXEGANJJZKJ-UHFFFAOYSA-N 0.000 description 1
- CLRXYKVOYODTOA-UHFFFAOYSA-N 2-(cyclopropylmethoxy)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOCC1CC1 CLRXYKVOYODTOA-UHFFFAOYSA-N 0.000 description 1
- MMRVDDUKOOOTTB-UHFFFAOYSA-N 2-[2-(cyclopropylmethoxy)ethoxy]-5-(oxiran-2-ylmethoxy)pyridine Chemical compound C1CC1COCCOC(N=C1)=CC=C1OCC1CO1 MMRVDDUKOOOTTB-UHFFFAOYSA-N 0.000 description 1
- NKWVEVOIKBAYKU-UHFFFAOYSA-N 2-[2-(cyclopropylmethoxy)ethoxy]-5-phenylmethoxypyridine Chemical compound C1CC1COCCOC(N=C1)=CC=C1OCC1=CC=CC=C1 NKWVEVOIKBAYKU-UHFFFAOYSA-N 0.000 description 1
- QLUMNDLJGBUHPB-UHFFFAOYSA-N 2-chloro-5-phenylmethoxypyridine Chemical compound C1=NC(Cl)=CC=C1OCC1=CC=CC=C1 QLUMNDLJGBUHPB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WPJYWANDOFUCGB-UHFFFAOYSA-N 6-[2-(cyclopropylmethoxy)ethoxy]pyridin-3-ol Chemical compound N1=CC(O)=CC=C1OCCOCC1CC1 WPJYWANDOFUCGB-UHFFFAOYSA-N 0.000 description 1
- 101100380241 Caenorhabditis elegans arx-2 gene Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 208000031229 Cardiomyopathies Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000021908 Myocardial disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- JERBWURCWWHQBK-ABLWVSNPSA-N [(2s)-3-tert-butyl-2-phenyl-1,3-oxazolidin-5-yl]methanol Chemical compound CC(C)(C)N1CC(CO)O[C@H]1C1=CC=CC=C1 JERBWURCWWHQBK-ABLWVSNPSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 101150092805 actc1 gene Proteins 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 239000000808 adrenergic beta-agonist Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000001955 cumulated effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8106005A FR2502618A1 (fr) | 1981-03-25 | 1981-03-25 | Derives de pyridine, leur preparation et leur application en therapeutique |
| FR8106005 | 1981-03-25 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI821034A0 FI821034A0 (fi) | 1982-03-24 |
| FI821034L FI821034L (fi) | 1982-09-26 |
| FI75808B FI75808B (fi) | 1988-04-29 |
| FI75808C true FI75808C (fi) | 1988-08-08 |
Family
ID=9256643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI821034A FI75808C (fi) | 1981-03-25 | 1982-03-24 | Foerfarande foer framstaellning av terapeutiskt anvaendbara aminopropanoloxipyridinderivat. |
Country Status (20)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998033793A1 (fr) * | 1997-01-30 | 1998-08-06 | Sanofi-Synthelabo | DERIVES DE α-AZACYCLOMETHYL BENZOTHIOPHENE ET DE α-AZACYCLOMETHYL BENZOFURANE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| FR2758820B1 (fr) * | 1997-01-30 | 1999-02-26 | Synthelabo | Derives de alpha-azacyclomethyl-benzofurane, leur preparation et leur application en therapeutique |
| JP7732668B2 (ja) | 2019-08-05 | 2025-09-02 | 北京志健金瑞生物医▲薬▼科技有限公司 | 窒素含有多環式縮合環系化合物、その薬学的組成物、製造方法及び用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115575A (en) * | 1973-02-20 | 1978-09-19 | Ciba-Geigy Corporation | 2-(3-Amino-2-hydroxy-propoxy)-pyrazines |
| AR206801A1 (es) * | 1973-02-20 | 1976-08-23 | Ciba Geigy Ag | Procedimiento para la elaboracion de derivados del 1-pirid loxi-2-hidroxi-3-amino-propano |
| US4195090A (en) * | 1973-02-20 | 1980-03-25 | Ciba-Geigy Corporation | 2-(3-Amino-2-hydroxy-propoxy)pyridine derivatives and pharmaceutical compositions therewith |
-
1981
- 1981-03-25 FR FR8106005A patent/FR2502618A1/fr active Granted
-
1982
- 1982-03-08 AT AT82400397T patent/ATE15895T1/de not_active IP Right Cessation
- 1982-03-08 DE DE8282400397T patent/DE3266607D1/de not_active Expired
- 1982-03-08 EP EP82400397A patent/EP0061379B1/fr not_active Expired
- 1982-03-23 MX MX191934A patent/MX156114A/es unknown
- 1982-03-23 GR GR67694A patent/GR75930B/el unknown
- 1982-03-24 CA CA000399301A patent/CA1185978A/en not_active Expired
- 1982-03-24 ZA ZA822008A patent/ZA822008B/xx unknown
- 1982-03-24 NZ NZ200118A patent/NZ200118A/en unknown
- 1982-03-24 HU HU82893A patent/HU186488B/hu not_active IP Right Cessation
- 1982-03-24 ES ES510724A patent/ES8303346A1/es not_active Expired
- 1982-03-24 IL IL65336A patent/IL65336A/xx unknown
- 1982-03-24 US US06/361,200 patent/US4406907A/en not_active Expired - Fee Related
- 1982-03-24 AR AR288854A patent/AR231281A1/es active
- 1982-03-24 DK DK133282A patent/DK156652C/da not_active IP Right Cessation
- 1982-03-24 FI FI821034A patent/FI75808C/fi not_active IP Right Cessation
- 1982-03-24 IE IE682/82A patent/IE52654B1/en unknown
- 1982-03-24 NO NO820979A patent/NO159850C/no unknown
- 1982-03-24 AU AU81873/82A patent/AU545747B2/en not_active Ceased
- 1982-03-24 JP JP57047061A patent/JPS57169462A/ja active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SYNTHELABO |