FI82053C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6-aminometyl-furo-(3,4-c)-pyridinderivat. - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6-aminometyl-furo-(3,4-c)-pyridinderivat. Download PDFInfo
- Publication number
- FI82053C FI82053C FI853288A FI853288A FI82053C FI 82053 C FI82053 C FI 82053C FI 853288 A FI853288 A FI 853288A FI 853288 A FI853288 A FI 853288A FI 82053 C FI82053 C FI 82053C
- Authority
- FI
- Finland
- Prior art keywords
- group
- furo
- hydroxy
- carbon atoms
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- IWTXSCSLCPQLDM-UHFFFAOYSA-N furo[3,4-c]pyridin-6-ylmethanamine Chemical class C1=NC(CN)=CC2=COC=C21 IWTXSCSLCPQLDM-UHFFFAOYSA-N 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 5
- KEKQEYBOTHGIGL-UHFFFAOYSA-N 7-hydroxyfuro[3,4-c]pyridine-6-carbaldehyde Chemical class C(=O)C1=C(C=2C(C=N1)=COC2)O KEKQEYBOTHGIGL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- QXMZUYAOYNKDBE-UHFFFAOYSA-N 6-(aminomethyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical class NCC1=NC=C2COCC2=C1O QXMZUYAOYNKDBE-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 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 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- -1 1,3-dihydro-3-propyl-6-formyl-7-hydroxy-furo- (3,4-c) -Pyridyl Chemical group 0.000 description 2
- LYGBFMCXQFCBNU-UHFFFAOYSA-N 6-(aminomethyl)-3-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=NC(CN)=C(O)C2=C1C(C)OC2 LYGBFMCXQFCBNU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229960003699 evans blue Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BIRWRIAEWIXFHT-UHFFFAOYSA-N furo[3,4-c]pyridin-7-ol Chemical class OC1=CN=CC2=COC=C12 BIRWRIAEWIXFHT-UHFFFAOYSA-N 0.000 description 2
- GJVNMIQVQXYJCP-UHFFFAOYSA-N furo[3,4-c]pyridine Chemical class C1=NC=CC2=[C]OC=C21 GJVNMIQVQXYJCP-UHFFFAOYSA-N 0.000 description 2
- 230000028709 inflammatory response Effects 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 229960003910 promethazine Drugs 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229960000278 theophylline Drugs 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
- MIPLSHYSJVWUNQ-UHFFFAOYSA-N 1-ethyl-7-hydroxy-3-(3,4,5-trimethoxyphenyl)-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound COC=1C=C(C=C(C1OC)OC)C1OC(C2=C1C=NC(=C2O)C=O)CC MIPLSHYSJVWUNQ-UHFFFAOYSA-N 0.000 description 1
- NCHKGGGEENCMSM-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[3-(dimethylamino)propyl]-7-hydroxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound CN(CCCC1OC(C=2C=NC(=C(C21)O)C=O)C2=CC=C(C=C2)Cl)C NCHKGGGEENCMSM-UHFFFAOYSA-N 0.000 description 1
- PJAFKGLPUVYSMP-UHFFFAOYSA-N 3-(4-chlorophenyl)-7-hydroxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound ClC1=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)C=O PJAFKGLPUVYSMP-UHFFFAOYSA-N 0.000 description 1
- JZYREUZTIFGONP-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-hydroxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound FC1=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)C=O JZYREUZTIFGONP-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- VDDIEIIJOFACDA-UHFFFAOYSA-N 3-cyclohexyl-3-(2,3-dichlorophenyl)-7-hydroxy-1H-furo[3,4-c]pyridine-6-carbaldehyde Chemical compound C1(CCCCC1)C1(OCC2=C1C=NC(=C2O)C=O)C2=C(C(=CC=C2)Cl)Cl VDDIEIIJOFACDA-UHFFFAOYSA-N 0.000 description 1
- XBKVOJFQPQOLBI-UHFFFAOYSA-N 3-cyclohexyl-7-hydroxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1(CCCCC1)C1OCC2=C1C=NC(=C2O)C=O XBKVOJFQPQOLBI-UHFFFAOYSA-N 0.000 description 1
- QJSDODKCGMHMMX-UHFFFAOYSA-N 3-ethyl-7-hydroxy-3-phenyl-1H-furo[3,4-c]pyridine-6-carbaldehyde Chemical compound C(C)C1(OCC2=C1C=NC(=C2O)C=O)C2=CC=CC=C2 QJSDODKCGMHMMX-UHFFFAOYSA-N 0.000 description 1
- HZUVPULGXJFPJD-UHFFFAOYSA-N 6-(aminomethyl)-3-(4-chlorophenyl)-1-[3-(dimethylamino)propyl]-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound CN(CCCC1OC(C=2C=NC(=C(C=21)O)CN)C1=CC=C(C=C1)Cl)C HZUVPULGXJFPJD-UHFFFAOYSA-N 0.000 description 1
- NUOCFODZOIJKJA-UHFFFAOYSA-N 6-(aminomethyl)-3-(4-methylphenyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1(=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)CN)C NUOCFODZOIJKJA-UHFFFAOYSA-N 0.000 description 1
- XASXDPGYTNGCKV-UHFFFAOYSA-N 6-(aminomethyl)-3-cyclohexyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1(CCCCC1)C1OCC2=C1C=NC(=C2O)CN XASXDPGYTNGCKV-UHFFFAOYSA-N 0.000 description 1
- VCPXJAOAYYWFQB-UHFFFAOYSA-N 6-(aminomethyl)-3-ethyl-3-phenyl-1H-furo[3,4-c]pyridin-7-ol Chemical compound C(C)C1(OCC2=C1C=NC(=C2O)CN)C2=CC=CC=C2 VCPXJAOAYYWFQB-UHFFFAOYSA-N 0.000 description 1
- HSJAIAWTKSEMII-UHFFFAOYSA-N 6-(aminomethyl)-3-phenyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1(=CC=CC=C1)C1OCC2=C1C=NC(=C2O)CN HSJAIAWTKSEMII-UHFFFAOYSA-N 0.000 description 1
- GNMILOMZPKZBLH-UHFFFAOYSA-N 6-(aminomethyl)-3-propyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C(CC)C1OCC2=C1C=NC(=C2O)CN GNMILOMZPKZBLH-UHFFFAOYSA-N 0.000 description 1
- IKWMZNFDXDHOOL-UHFFFAOYSA-N 7-hydroxy-3-(4-methoxyphenyl)-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound COC1=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)C=O IKWMZNFDXDHOOL-UHFFFAOYSA-N 0.000 description 1
- NPGWFLVNYKKUMM-UHFFFAOYSA-N 7-hydroxy-3-phenyl-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1(=CC=CC=C1)C1OCC2=C1C=NC(=C2O)C=O NPGWFLVNYKKUMM-UHFFFAOYSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- HWGQEDDEYCKVTG-UHFFFAOYSA-N ClC=1C=C(C=CC1)C1OCC=2C=NC(=C(C21)O)C=O Chemical compound ClC=1C=C(C=CC1)C1OCC=2C=NC(=C(C21)O)C=O HWGQEDDEYCKVTG-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- YVECRCZZSGAGOW-UHFFFAOYSA-N furo[3,4-c]pyridin-1-ol Chemical compound C1=NC=CC2=C(O)OC=C21 YVECRCZZSGAGOW-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
- 229960000645 histamine hydrochloride Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229960005042 mequitazine Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 210000005164 penile vein Anatomy 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8422379 | 1984-09-05 | ||
| GB848422379A GB8422379D0 (en) | 1984-09-05 | 1984-09-05 | Derivatives |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI853288A0 FI853288A0 (fi) | 1985-08-28 |
| FI853288L FI853288L (fi) | 1986-03-06 |
| FI82053B FI82053B (fi) | 1990-09-28 |
| FI82053C true FI82053C (fi) | 1991-01-10 |
Family
ID=10566274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI853288A FI82053C (fi) | 1984-09-05 | 1985-08-28 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6-aminometyl-furo-(3,4-c)-pyridinderivat. |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS6168490A (en, 2012) |
| AT (1) | AT394557B (en, 2012) |
| BE (1) | BE903121A (en, 2012) |
| CA (1) | CA1300150C (en, 2012) |
| CH (1) | CH665642A5 (en, 2012) |
| DE (1) | DE3531747A1 (en, 2012) |
| DK (1) | DK159318C (en, 2012) |
| ES (1) | ES8604966A1 (en, 2012) |
| FI (1) | FI82053C (en, 2012) |
| FR (2) | FR2569699A1 (en, 2012) |
| GB (2) | GB8422379D0 (en, 2012) |
| HK (1) | HK10489A (en, 2012) |
| IE (1) | IE58583B1 (en, 2012) |
| IT (1) | IT1188188B (en, 2012) |
| LU (1) | LU86053A1 (en, 2012) |
| MA (1) | MA20517A1 (en, 2012) |
| MY (1) | MY103211A (en, 2012) |
| NL (1) | NL8502412A (en, 2012) |
| NO (1) | NO160143C (en, 2012) |
| OA (1) | OA08157A (en, 2012) |
| PT (1) | PT81087B (en, 2012) |
| SE (1) | SE461394B (en, 2012) |
| ZA (1) | ZA856089B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8414559D0 (en) * | 1984-06-07 | 1984-07-11 | Scras | Pyridine derivatives |
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| GB8907480D0 (en) * | 1989-04-03 | 1989-05-17 | Scaras Societe De Conseils De | Separation of insomers of furo(3,4-c)pyridine derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
| IN156817B (en, 2012) * | 1981-02-10 | 1985-11-09 | Scras | |
| ZA842029B (en) * | 1983-04-05 | 1984-10-31 | Scras | Furo-(3,4-c)-pyridine derivatives preparation thereof and therapeutic compositions containing the same |
| GB8330517D0 (en) * | 1983-11-16 | 1983-12-21 | Scras | 6-vinyl-furo-(3,4-c)pyridine derivatives |
-
1984
- 1984-09-05 GB GB848422379A patent/GB8422379D0/en active Pending
-
1985
- 1985-08-09 GB GB08520007A patent/GB2164037B/en not_active Expired
- 1985-08-12 ZA ZA856089A patent/ZA856089B/xx unknown
- 1985-08-22 LU LU86053A patent/LU86053A1/fr unknown
- 1985-08-26 BE BE0/215501A patent/BE903121A/fr not_active IP Right Cessation
- 1985-08-28 FI FI853288A patent/FI82053C/fi not_active IP Right Cessation
- 1985-08-29 CH CH3716/85A patent/CH665642A5/fr not_active IP Right Cessation
- 1985-08-30 FR FR8512918A patent/FR2569699A1/fr active Pending
- 1985-08-30 FR FR858512919A patent/FR2569562B1/fr not_active Expired
- 1985-09-03 CA CA000489880A patent/CA1300150C/en not_active Expired - Lifetime
- 1985-09-03 NL NL8502412A patent/NL8502412A/nl active Search and Examination
- 1985-09-04 PT PT81087A patent/PT81087B/pt not_active IP Right Cessation
- 1985-09-04 ES ES546702A patent/ES8604966A1/es not_active Expired
- 1985-09-04 SE SE8504119A patent/SE461394B/sv not_active IP Right Cessation
- 1985-09-04 DK DK402885A patent/DK159318C/da not_active IP Right Cessation
- 1985-09-04 NO NO853475A patent/NO160143C/no unknown
- 1985-09-04 IE IE218285A patent/IE58583B1/en not_active IP Right Cessation
- 1985-09-05 DE DE19853531747 patent/DE3531747A1/de active Granted
- 1985-09-05 IT IT22067/85A patent/IT1188188B/it active
- 1985-09-05 OA OA58672A patent/OA08157A/xx unknown
- 1985-09-05 JP JP60195015A patent/JPS6168490A/ja active Granted
- 1985-09-05 AT AT0260285A patent/AT394557B/de not_active IP Right Cessation
- 1985-09-05 MA MA20743A patent/MA20517A1/fr unknown
-
1988
- 1988-02-16 MY MYPI88000163A patent/MY103211A/en unknown
-
1989
- 1989-02-02 HK HK104/89A patent/HK10489A/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
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| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: SOCIETE DE CONSEILS DE RECHERCHES ET D |