FI79852C - Foerfarande foer framstaellning av farmakologiskt anvaendbara 6-vinyl-furo-(3,4-c)-pyridinderivat. - Google Patents
Foerfarande foer framstaellning av farmakologiskt anvaendbara 6-vinyl-furo-(3,4-c)-pyridinderivat. Download PDFInfo
- Publication number
- FI79852C FI79852C FI844279A FI844279A FI79852C FI 79852 C FI79852 C FI 79852C FI 844279 A FI844279 A FI 844279A FI 844279 A FI844279 A FI 844279A FI 79852 C FI79852 C FI 79852C
- Authority
- FI
- Finland
- Prior art keywords
- furo
- dihydro
- pyridine
- vinyl
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 9
- JYNVFJZLBWIXBQ-UHFFFAOYSA-N 6-ethenylfuro[3,4-c]pyridine Chemical class C1=NC(C=C)=CC2=COC=C21 JYNVFJZLBWIXBQ-UHFFFAOYSA-N 0.000 title description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 5
- HNYKBJGQIWXQIA-UHFFFAOYSA-N 6-ethenyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical class N1=C(C=C)C(O)=C2COCC2=C1 HNYKBJGQIWXQIA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 238000010306 acid treatment Methods 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 25
- 239000007858 starting material Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 3
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229940116269 uric acid Drugs 0.000 description 3
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 description 2
- LHCMMHHWVIUEJS-UHFFFAOYSA-N 6-(chloromethyl)-3-(4-chlorophenyl)-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine Chemical compound ClCC1=NC=C2C(C=3C=CC(Cl)=CC=3)OCC2=C1OCC1=CC=CC=C1 LHCMMHHWVIUEJS-UHFFFAOYSA-N 0.000 description 2
- RBBZFCJQLKJRNM-UHFFFAOYSA-N 6-ethenyl-3-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=NC(C=C)=C(O)C2=C1C(C)OC2 RBBZFCJQLKJRNM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- GHZHWDWADLAOIQ-UHFFFAOYSA-N 2,3-bis(4-hydroxyphenyl)propionitrile Chemical compound C1=CC(O)=CC=C1CC(C#N)C1=CC=C(O)C=C1 GHZHWDWADLAOIQ-UHFFFAOYSA-N 0.000 description 1
- GBWYCLRVNAYVTG-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-ethenyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C12=CN=C(C=C)C(O)=C2COC1C1=CC=C(Cl)C=C1 GBWYCLRVNAYVTG-UHFFFAOYSA-N 0.000 description 1
- DEHRYMBZUAIZBB-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-ethenyl-3-ethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound O1CC(C(=C(C=C)N=C2)O)=C2C1(CC)C1=CC=C(Cl)C=C1 DEHRYMBZUAIZBB-UHFFFAOYSA-N 0.000 description 1
- MJMNTWOKOKJOQH-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-ethenyl-3-methyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound O1CC(C(=C(C=C)N=C2)O)=C2C1(C)C1=CC=C(Cl)C=C1 MJMNTWOKOKJOQH-UHFFFAOYSA-N 0.000 description 1
- NKNASSUVZQRSNI-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-methyl-5-oxido-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridin-5-ium Chemical compound C1=2COC(C=3C=CC(Cl)=CC=3)C=2C=[N+]([O-])C(C)=C1OCC1=CC=CC=C1 NKNASSUVZQRSNI-UHFFFAOYSA-N 0.000 description 1
- NLNBWNQDPBQCJS-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-methyl-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine Chemical compound CC1=NC=C2C(C=3C=CC(Cl)=CC=3)OCC2=C1OCC1=CC=CC=C1 NLNBWNQDPBQCJS-UHFFFAOYSA-N 0.000 description 1
- RTQFXWWMGPETCR-UHFFFAOYSA-N 3-cyclohexyl-3-(2,3-dichlorophenyl)-6-ethenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C12=CN=C(C=C)C(O)=C2COC1(C=1C(=C(Cl)C=CC=1)Cl)C1CCCCC1 RTQFXWWMGPETCR-UHFFFAOYSA-N 0.000 description 1
- AFHKCMHSONKIEZ-UHFFFAOYSA-N 6-(chloromethyl)-3,3-dimethyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound CC1(C)OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 AFHKCMHSONKIEZ-UHFFFAOYSA-N 0.000 description 1
- YFIADQMCJWMZQS-UHFFFAOYSA-N 6-(chloromethyl)-3,3-diphenyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound C=1C=CC=CC=1COC=1C(CCl)=NC=C2C=1COC2(C=1C=CC=CC=1)C1=CC=CC=C1 YFIADQMCJWMZQS-UHFFFAOYSA-N 0.000 description 1
- WVSSCFLXTJYQQK-UHFFFAOYSA-N 6-(chloromethyl)-3-(4-chlorophenyl)-3-ethyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound C=1C=C(Cl)C=CC=1C1(CC)OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 WVSSCFLXTJYQQK-UHFFFAOYSA-N 0.000 description 1
- ASCKJMZNZOULFH-UHFFFAOYSA-N 6-(chloromethyl)-3-(4-chlorophenyl)-3-methyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound C=1C=C(Cl)C=CC=1C1(C)OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 ASCKJMZNZOULFH-UHFFFAOYSA-N 0.000 description 1
- KTLAFBRMBJFHMH-UHFFFAOYSA-N 6-(chloromethyl)-3-(4-fluorophenyl)-3-methyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound C=1C=C(F)C=CC=1C1(C)OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 KTLAFBRMBJFHMH-UHFFFAOYSA-N 0.000 description 1
- COKKCYOPAOSXAR-UHFFFAOYSA-N 6-(chloromethyl)-3-(4-fluorophenyl)-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine Chemical compound C1=CC(F)=CC=C1C1C(C=NC(CCl)=C2OCC=3C=CC=CC=3)=C2CO1 COKKCYOPAOSXAR-UHFFFAOYSA-N 0.000 description 1
- LHPYNEOLUYWLHM-UHFFFAOYSA-N 6-(chloromethyl)-3-(4-methoxyphenyl)-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine Chemical compound C1=CC(OC)=CC=C1C1C(C=NC(CCl)=C2OCC=3C=CC=CC=3)=C2CO1 LHPYNEOLUYWLHM-UHFFFAOYSA-N 0.000 description 1
- NDELLWURJCIBRP-UHFFFAOYSA-N 6-(chloromethyl)-3-cyclohexyl-3-(2,3-dichlorophenyl)-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound C=1C=CC=CC=1COC=1C(CCl)=NC=C2C=1COC2(C=1C(=C(Cl)C=CC=1)Cl)C1CCCCC1 NDELLWURJCIBRP-UHFFFAOYSA-N 0.000 description 1
- RIQNPNLDMRHCFF-UHFFFAOYSA-N 6-(chloromethyl)-3-methyl-3-pentyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound CCCCCC1(C)OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 RIQNPNLDMRHCFF-UHFFFAOYSA-N 0.000 description 1
- FCMCYYVQPDLPRY-UHFFFAOYSA-N 6-(chloromethyl)-3-phenyl-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine Chemical compound ClCC1=NC=C2C(C=3C=CC=CC=3)OCC2=C1OCC1=CC=CC=C1 FCMCYYVQPDLPRY-UHFFFAOYSA-N 0.000 description 1
- VYNQHMFJTOFBHU-UHFFFAOYSA-N 6-(chloromethyl)-7-phenylmethoxy-3-propyl-1,3-dihydrofuro[3,4-c]pyridine Chemical compound CCCC1OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 VYNQHMFJTOFBHU-UHFFFAOYSA-N 0.000 description 1
- IWUJKCFGZGXOHQ-UHFFFAOYSA-N 6-ethenyl-3,3-diphenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C12=CN=C(C=C)C(O)=C2COC1(C=1C=CC=CC=1)C1=CC=CC=C1 IWUJKCFGZGXOHQ-UHFFFAOYSA-N 0.000 description 1
- DLODMQNWTIIEKQ-UHFFFAOYSA-N 6-ethenyl-3-(4-fluorophenyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C12=CN=C(C=C)C(O)=C2COC1C1=CC=C(F)C=C1 DLODMQNWTIIEKQ-UHFFFAOYSA-N 0.000 description 1
- PDXQUUWSXAOEKG-UHFFFAOYSA-N 6-ethenyl-3-(4-fluorophenyl)-3-methyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound O1CC(C(=C(C=C)N=C2)O)=C2C1(C)C1=CC=C(F)C=C1 PDXQUUWSXAOEKG-UHFFFAOYSA-N 0.000 description 1
- FPQZWXAPDBMYCA-UHFFFAOYSA-N 6-ethenyl-3-methyl-3-pentyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C1=NC(C=C)=C(O)C2=C1C(CCCCC)(C)OC2 FPQZWXAPDBMYCA-UHFFFAOYSA-N 0.000 description 1
- GLKGCPLDRBCHDW-UHFFFAOYSA-N 6-ethenyl-3-methyl-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine Chemical compound CC1OCC2=C1C=NC(C=C)=C2OCC1=CC=CC=C1 GLKGCPLDRBCHDW-UHFFFAOYSA-N 0.000 description 1
- MCJMDPRKWGJGGX-UHFFFAOYSA-N 6-ethenyl-3-phenyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C12=CN=C(C=C)C(O)=C2COC1C1=CC=CC=C1 MCJMDPRKWGJGGX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WWQSAFNGTGNZMJ-UHFFFAOYSA-N CC1C2=CN=C(C(=C2CO1)OCC3=CC=CC=C3C)Cl Chemical compound CC1C2=CN=C(C(=C2CO1)OCC3=CC=CC=C3C)Cl WWQSAFNGTGNZMJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MNYARIILPGRTQL-WPRPVWTQSA-N Ephedroxane Chemical compound O1C(=O)N(C)[C@@H](C)[C@H]1C1=CC=CC=C1 MNYARIILPGRTQL-WPRPVWTQSA-N 0.000 description 1
- 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 1
- 241000699670 Mus sp. Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PHJBISJMBQUNIK-UHFFFAOYSA-N [3-(4-chlorophenyl)-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridin-6-yl]methanol Chemical compound OCC1=NC=C2C(C=3C=CC(Cl)=CC=3)OCC2=C1OCC1=CC=CC=C1 PHJBISJMBQUNIK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838330517A GB8330517D0 (en) | 1983-11-16 | 1983-11-16 | 6-vinyl-furo-(3,4-c)pyridine derivatives |
| GB8330517 | 1983-11-16 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI844279A0 FI844279A0 (fi) | 1984-11-01 |
| FI844279L FI844279L (fi) | 1985-05-17 |
| FI79852B FI79852B (fi) | 1989-11-30 |
| FI79852C true FI79852C (fi) | 1990-03-12 |
Family
ID=10551816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI844279A FI79852C (fi) | 1983-11-16 | 1984-11-01 | Foerfarande foer framstaellning av farmakologiskt anvaendbara 6-vinyl-furo-(3,4-c)-pyridinderivat. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4569939A (en:Method) |
| JP (1) | JPS60112793A (en:Method) |
| AT (1) | AT391867B (en:Method) |
| BE (1) | BE900942A (en:Method) |
| CA (1) | CA1257271A (en:Method) |
| CH (1) | CH660738A5 (en:Method) |
| DE (1) | DE3442035A1 (en:Method) |
| DK (1) | DK157870C (en:Method) |
| DZ (1) | DZ701A1 (en:Method) |
| ES (1) | ES8600299A1 (en:Method) |
| FI (1) | FI79852C (en:Method) |
| FR (2) | FR2554719B1 (en:Method) |
| GB (2) | GB8330517D0 (en:Method) |
| HK (1) | HK36087A (en:Method) |
| IE (1) | IE58005B1 (en:Method) |
| IT (1) | IT1213246B (en:Method) |
| LU (1) | LU85635A1 (en:Method) |
| MA (1) | MA20259A1 (en:Method) |
| MY (1) | MY101721A (en:Method) |
| NL (1) | NL8403353A (en:Method) |
| OA (1) | OA07864A (en:Method) |
| PT (1) | PT79511B (en:Method) |
| SE (1) | SE458116B (en:Method) |
| SG (1) | SG6687G (en:Method) |
| ZA (1) | ZA848130B (en:Method) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8402740D0 (en) * | 1984-02-02 | 1984-03-07 | Scras | Furo-(3 4-c)-pyridine derivatives |
| GB8422379D0 (en) * | 1984-09-05 | 1984-10-10 | Scras | Derivatives |
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| GB8917168D0 (en) * | 1989-07-27 | 1989-09-13 | Scras | Asymmetric synthesis of furo(3,4-c)pyridine derivatives |
| US5130252A (en) * | 1990-05-14 | 1992-07-14 | Synthetech, Inc. | Resolution of furopyridine enantiomers and synthetic precursors thereof |
| DE59203008D1 (de) * | 1991-04-24 | 1995-08-31 | Ciba Geigy Ag | Fliessfähige wässrige Dispersionen von Polycarbonsäure-Korrosionsinhibitoren. |
| DK1169322T3 (da) | 1999-03-08 | 2006-03-06 | Medicure Inc | Pyridoxalanaloger til behandling af lidelser foranlediget af vitamin B6-mangel |
| AU5840200A (en) * | 1999-07-13 | 2001-01-30 | Medicure Inc. | Treatment of diabetes and related pathologies |
| EP1872797A3 (en) | 1999-08-24 | 2008-04-02 | Medicure International Inc. | Treatment of cardiovascular and related pathologies |
| ES2305994T3 (es) | 2000-02-29 | 2008-11-01 | Medicure International Inc. | Fosfonatos cardioprotectores. |
| US7442689B2 (en) * | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| AU784840B2 (en) | 2000-03-28 | 2006-07-06 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel uses |
| WO2002004421A2 (en) | 2000-07-07 | 2002-01-17 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: cardiovascular therapeutics |
| US6897228B2 (en) * | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| US20040121988A1 (en) * | 2001-03-28 | 2004-06-24 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US20040186077A1 (en) * | 2003-03-17 | 2004-09-23 | Medicure International Inc. | Novel heteroaryl phosphonates as cardioprotective agents |
| US20060019929A1 (en) * | 2004-07-07 | 2006-01-26 | Albert Friesen | Combination therapies employing platelet aggregation drugs |
| US20070060549A1 (en) * | 2004-08-10 | 2007-03-15 | Friesen Albert D | Combination therapies employing ace inhibitors and uses thereof for the treatment of diabetic disorders |
| AU2005304220A1 (en) * | 2004-10-28 | 2006-05-18 | Medicure International Inc. | Dual antiplatelet/anticoagulant pyridoxine analogs |
| US7459468B2 (en) * | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| US20060094749A1 (en) * | 2004-10-28 | 2006-05-04 | Medicure International Inc. | Substituted pyridoxines as anti-platelet agents |
| JP2009517411A (ja) * | 2005-11-28 | 2009-04-30 | メディキュア インターナショナル インコーポレーテッド | 心血管及び関連病状の処置のための調剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
| GB2008582B (en) * | 1977-11-25 | 1982-04-28 | Scras | Pyridine derivative |
| IN156817B (en:Method) * | 1981-02-10 | 1985-11-09 | Scras |
-
1983
- 1983-11-16 GB GB838330517A patent/GB8330517D0/en active Pending
-
1984
- 1984-10-17 ZA ZA848130A patent/ZA848130B/xx unknown
- 1984-10-19 GB GB08426490A patent/GB2149782B/en not_active Expired
- 1984-10-26 CH CH5320/84A patent/CH660738A5/fr not_active IP Right Cessation
- 1984-10-30 BE BE0/213926A patent/BE900942A/fr not_active IP Right Cessation
- 1984-11-01 FI FI844279A patent/FI79852C/fi not_active IP Right Cessation
- 1984-11-01 JP JP59229029A patent/JPS60112793A/ja active Granted
- 1984-11-01 MA MA20483A patent/MA20259A1/fr unknown
- 1984-11-05 US US06/668,399 patent/US4569939A/en not_active Expired - Lifetime
- 1984-11-05 NL NL8403353A patent/NL8403353A/nl not_active Application Discontinuation
- 1984-11-07 LU LU85635A patent/LU85635A1/fr unknown
- 1984-11-14 DZ DZ847328A patent/DZ701A1/fr active
- 1984-11-14 SE SE8405710A patent/SE458116B/sv not_active IP Right Cessation
- 1984-11-14 CA CA000467828A patent/CA1257271A/en not_active Expired
- 1984-11-14 IT IT8423565A patent/IT1213246B/it active
- 1984-11-15 DK DK542584A patent/DK157870C/da not_active IP Right Cessation
- 1984-11-15 ES ES537665A patent/ES8600299A1/es not_active Expired
- 1984-11-15 IE IE2930/84A patent/IE58005B1/en not_active IP Right Cessation
- 1984-11-16 FR FR8417481A patent/FR2554719B1/fr not_active Expired
- 1984-11-16 AT AT0364384A patent/AT391867B/de not_active IP Right Cessation
- 1984-11-16 OA OA58441A patent/OA07864A/xx unknown
- 1984-11-16 FR FR8417480A patent/FR2554817B1/fr not_active Expired
- 1984-11-16 PT PT79511A patent/PT79511B/pt not_active IP Right Cessation
- 1984-11-16 DE DE19843442035 patent/DE3442035A1/de not_active Ceased
-
1987
- 1987-01-28 SG SG66/87A patent/SG6687G/en unknown
- 1987-03-31 MY MYPI87000398A patent/MY101721A/en unknown
- 1987-04-30 HK HK360/87A patent/HK36087A/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: SOCIETE DE CONSEILS DE RECHERCHES ET D APPLICATION |