NL8403353A - Nieuwe 6-vinyl-furo-(3,4-c)-pyridinederivaten, hun bereiding en farmaceutische preparaten die ze bevatten. - Google Patents
Nieuwe 6-vinyl-furo-(3,4-c)-pyridinederivaten, hun bereiding en farmaceutische preparaten die ze bevatten. Download PDFInfo
- Publication number
- NL8403353A NL8403353A NL8403353A NL8403353A NL8403353A NL 8403353 A NL8403353 A NL 8403353A NL 8403353 A NL8403353 A NL 8403353A NL 8403353 A NL8403353 A NL 8403353A NL 8403353 A NL8403353 A NL 8403353A
- Authority
- NL
- Netherlands
- Prior art keywords
- furo
- dihydro
- pyridine
- vinyl
- benzoxy
- Prior art date
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 7
- 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
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 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 4
- 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
- 238000009835 boiling Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000010306 acid treatment Methods 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 238000003756 stirring Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000000203 mixture 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
- 239000007858 starting material Substances 0.000 description 4
- -1 vinyl 7-hydroxy-furo (3,4-c) -pyridine Chemical compound 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
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- UWJGNEHXONHKGW-UHFFFAOYSA-N 1-(chloromethyl)-7-phenylmethoxyfuro[3,4-c]pyridine Chemical compound ClCC=1OC=C2C=NC=C(C2=1)OCC1=CC=CC=C1 UWJGNEHXONHKGW-UHFFFAOYSA-N 0.000 description 2
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 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
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 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
- 229940116269 uric acid Drugs 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
- ORVPKQVDQWSVML-UHFFFAOYSA-N 1-phenylmethoxyfuro[3,4-c]pyridine Chemical compound C(C1=CC=CC=C1)OC=1OC=C2C=NC=CC21 ORVPKQVDQWSVML-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
- 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
- WIXLGDNVLQGCRD-UHFFFAOYSA-N 3-cyclohexyl-6-ethenyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C12=CN=C(C=C)C(O)=C2COC1C1CCCCC1 WIXLGDNVLQGCRD-UHFFFAOYSA-N 0.000 description 1
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-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
- 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
- WPSYAVDEDQCTCO-UHFFFAOYSA-N 6-(chloromethyl)-3-cyclohexyl-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine Chemical compound ClCC1=NC=C2C(C3CCCCC3)OCC2=C1OCC1=CC=CC=C1 WPSYAVDEDQCTCO-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
- PWLHWLQOJWJRNE-UHFFFAOYSA-N 6-(chloromethyl)-3-methyl-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine Chemical compound CC1OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 PWLHWLQOJWJRNE-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
- ILANKVWOLFZSBA-UHFFFAOYSA-N 6-ethenyl-3,3-dimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C1=NC(C=C)=C(O)C2=C1C(C)(C)OC2 ILANKVWOLFZSBA-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
- TZOLFSKKRDLHDT-UHFFFAOYSA-N 6-ethenyl-3-(4-methoxyphenyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=CC(OC)=CC=C1C1C(C=NC(C=C)=C2O)=C2CO1 TZOLFSKKRDLHDT-UHFFFAOYSA-N 0.000 description 1
- 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 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
- HMZFVWPOQCNTJH-UHFFFAOYSA-N 6-ethenyl-3-propyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=NC(C=C)=C(O)C2=C1C(CCC)OC2 HMZFVWPOQCNTJH-UHFFFAOYSA-N 0.000 description 1
- NZOCLVWZHBNOKT-UHFFFAOYSA-N 6-methylfuro[3,4-c]pyridin-7-ol Chemical compound OC1=C(C)N=CC2=COC=C21 NZOCLVWZHBNOKT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-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
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000004880 Polyuria Diseases 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 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
- 239000004927 clay Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 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
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 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
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 (1)
| Publication Number | Publication Date |
|---|---|
| NL8403353A true NL8403353A (nl) | 1985-06-17 |
Family
ID=10551816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8403353A NL8403353A (nl) | 1983-11-16 | 1984-11-05 | Nieuwe 6-vinyl-furo-(3,4-c)-pyridinederivaten, hun bereiding en farmaceutische preparaten die ze bevatten. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4569939A (fr) |
| JP (1) | JPS60112793A (fr) |
| AT (1) | AT391867B (fr) |
| BE (1) | BE900942A (fr) |
| CA (1) | CA1257271A (fr) |
| CH (1) | CH660738A5 (fr) |
| DE (1) | DE3442035A1 (fr) |
| DK (1) | DK157870C (fr) |
| DZ (1) | DZ701A1 (fr) |
| ES (1) | ES537665A0 (fr) |
| FI (1) | FI79852C (fr) |
| FR (2) | FR2554817B1 (fr) |
| GB (2) | GB8330517D0 (fr) |
| HK (1) | HK36087A (fr) |
| IE (1) | IE58005B1 (fr) |
| IT (1) | IT1213246B (fr) |
| LU (1) | LU85635A1 (fr) |
| MA (1) | MA20259A1 (fr) |
| MY (1) | MY101721A (fr) |
| NL (1) | NL8403353A (fr) |
| OA (1) | OA07864A (fr) |
| PT (1) | PT79511B (fr) |
| SE (1) | SE458116B (fr) |
| SG (1) | SG6687G (fr) |
| ZA (1) | ZA848130B (fr) |
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. |
| US6339085B1 (en) | 1999-03-08 | 2002-01-15 | The University Of Manitoba | Therapeutics for cardiovascular and related diseases |
| US6489345B1 (en) | 1999-07-13 | 2002-12-03 | Medicure, Inc. | Treatment of diabetes and related pathologies |
| EP1872797A3 (fr) * | 1999-08-24 | 2008-04-02 | Medicure International Inc. | Traitement des pathologies cardiovasculaires et associées |
| JP2003525303A (ja) | 2000-02-29 | 2003-08-26 | メディキュア インターナショナル インコーポレイテッド | 心臓保護ホスホン酸塩およびマロン酸塩 |
| US7442689B2 (en) * | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| EP1278526A2 (fr) | 2000-03-28 | 2003-01-29 | Medicure International Inc. | Traitement d'une maladie vasculaire cerebrale |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel uses |
| ATE364595T1 (de) | 2000-07-07 | 2007-07-15 | Medicure Int Inc | Pyridoxin- und pyridoxalanaloga als cardiovasculäre therapeutika |
| 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 |
| EP1773370A1 (fr) * | 2004-07-07 | 2007-04-18 | Medicure International Inc. | Polytherapies faisant intervenir des inhibiteurs d'agregation plaquettaire |
| 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 |
| WO2006050598A1 (fr) * | 2004-10-28 | 2006-05-18 | Medicure International Inc. | Analogues de pyridoxine à double activité anti-plaquettes et anti-coagulantes |
| 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 |
| WO2007059631A1 (fr) * | 2005-11-28 | 2007-05-31 | Medicure International Inc. | Dosage selectionne pour le traitement de pathologies cardiovasculaires et apparentees |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2008582B (en) * | 1977-11-25 | 1982-04-28 | Scras | Pyridine derivative |
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
| IN156817B (fr) * | 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 JP JP59229029A patent/JPS60112793A/ja active Granted
- 1984-11-01 FI FI844279A patent/FI79852C/fi not_active IP Right Cessation
- 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 SE SE8405710A patent/SE458116B/sv not_active IP Right Cessation
- 1984-11-14 CA CA000467828A patent/CA1257271A/fr not_active Expired
- 1984-11-14 IT IT8423565A patent/IT1213246B/it active
- 1984-11-14 DZ DZ847328A patent/DZ701A1/fr active
- 1984-11-15 DK DK542584A patent/DK157870C/da not_active IP Right Cessation
- 1984-11-15 ES ES537665A patent/ES537665A0/es active Granted
- 1984-11-15 IE IE2930/84A patent/IE58005B1/en not_active IP Right Cessation
- 1984-11-16 FR FR8417480A patent/FR2554817B1/fr not_active Expired
- 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 PT PT79511A patent/PT79511B/pt not_active IP Right Cessation
- 1984-11-16 DE DE19843442035 patent/DE3442035A1/de not_active Ceased
- 1984-11-16 OA OA58441A patent/OA07864A/fr unknown
-
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
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL8403353A (nl) | Nieuwe 6-vinyl-furo-(3,4-c)-pyridinederivaten, hun bereiding en farmaceutische preparaten die ze bevatten. | |
| CA1257269A (fr) | Derives de furo-(3,4-c)-pyridine; preparation ett compositions therapeutiques qui en renferment | |
| FI75347C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla furo-(3,4-c)-pyridinderivat. | |
| US4735950A (en) | Furo-(3,4-C)-pyridine derivatives and therapeutic composition containing the same | |
| KR880002711B1 (ko) | 피리다진 유도체의 제조방법 | |
| EP0010361B1 (fr) | Bis-imidazoles, leur préparation et compositions pharmaceutiques les contenant | |
| CA1169081A (fr) | 8-aminoalkyl-4-alkylisopsoralenes | |
| IE50160B1 (en) | 8-aminoalkyl-4-alkylpsoralens | |
| US4036983A (en) | Ferrocene compounds and pharmaceutical composition for use in treatment of iron deficiency in an animal | |
| CA1040643A (fr) | Complexes d'or de phosphine ou de phosphite de l'acide thiobenzoique et de thiophenols substitues | |
| JPH0710863B2 (ja) | エーテル化若しくはエステル化しうるジヒドロキシ基により位置２で置換された４―ｏｈキノリンカルボン酸の新規の誘導体、その製造方法、及び医薬としてのその使用 | |
| EP0058009A1 (fr) | Dérivés de benzanilide et composés pharmaceutiques les contenant | |
| CA2005990C (fr) | Cetones furaniques a radical aryloxy substitue antiviraux | |
| US4128648A (en) | Substituted pyrano[4,3-d]-thiazolo[3,2-a]pyrimidines | |
| RU2068415C1 (ru) | 5,7-диокси-2-метил-8-/4-(3-окси-1-(1-пропил)пиперидинил/-4н-1-бензопиран-4-он или его стереоизомеры или фармакологически приемлемые кислотно-аддитивные соли и способ их получения | |
| GB2137618A (en) | Furo-(3,4-c)-pyridine derivatives | |
| KR0154281B1 (ko) | 접합고리 피리딘을 함유한 벤즈이미다졸 유도체 | |
| JPS62108880A (ja) | ３−イミノ−ピリダジンの誘導体、それらを得る方法、およびそれらを含有する薬学的組成物 | |
| JPS637186B2 (fr) | ||
| CS8905106A3 (en) | Process for preparing novel thieno/3', 4'-4,5/imidazo/2,1-b/ thiazole derivatives | |
| NL8100572A (nl) | Werkwijze voor het bereiden van een geneesmiddel met een secretieremmende en ulcusvormingremmende werking dat een pyridobenzodiazepinon dat door een diallylaminoacylgroep is gesubstitueerd en/of een fysiologisch verdraagbaar zuuradditiezout daarvan bevat en voor het bereiden van een dergelijk derivaat en/of een zuuradditiezout daarvan. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed | ||
| BV | The patent application has lapsed |