DE3531747C2 - - Google Patents

Info

Publication number: DE3531747C2
Authority: DE; Germany
Prior art keywords: furo; dihydro; hydroxy; radical; pyridine
Prior art date: 1984-09-05
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

DE3531747A

Other languages

German (de)

English (en)

Other versions

DE3531747A1 (de

Inventor

Andre Paris Fr Esanu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ipsen Pharma SAS

Original Assignee

Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-09-05

Filing date

1985-09-05

Publication date

1990-09-06

1985-09-05 Application filed by Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS filed Critical Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS

1986-03-13 Publication of DE3531747A1 publication Critical patent/DE3531747A1/de

1990-09-06 Application granted granted Critical

1990-09-06 Publication of DE3531747C2 publication Critical patent/DE3531747C2/de

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
-1 3,4,5-trimethoxyphenyl-ethyl Chemical group 0.000 claims description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 7
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 4
238000000034 method Methods 0.000 claims description 4
150000003839 salts Chemical class 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
239000003054 catalyst Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
125000001153 fluoro group Chemical group F* 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
229920006395 saturated elastomer Polymers 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
229940079593 drug Drugs 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000000047 product Substances 0.000 description 27
235000011054 acetic acid Nutrition 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
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
239000000203 mixture Substances 0.000 description 5
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 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
229960000583 acetic acid Drugs 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
KEKQEYBOTHGIGL-UHFFFAOYSA-N 7-hydroxyfuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C(=O)C1=C(C=2C(C=N1)=COC2)O KEKQEYBOTHGIGL-UHFFFAOYSA-N 0.000 description 3
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 3
241001465754 Metazoa Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
208000024780 Urticaria Diseases 0.000 description 3
229960003699 evans blue Drugs 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 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
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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 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
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 2
230000001387 anti-histamine Effects 0.000 description 2
239000000739 antihistaminic agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 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
230000004054 inflammatory process Effects 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
238000001990 intravenous administration Methods 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
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
238000013222 sprague-dawley male rat Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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
ZQBKYDIVYUVOKL-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-(hydroxymethyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound ClC1=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)CO ZQBKYDIVYUVOKL-UHFFFAOYSA-N 0.000 description 1
VVZFVTBHZIUIGP-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-methyl-5-oxido-1,3-dihydrofuro[3,4-c]pyridin-5-ium-7-ol Chemical compound ClC1=CC=C(C=C1)C1OCC2=C1C=[N+](C(=C2O)C)[O-] VVZFVTBHZIUIGP-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
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
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
GCZHURKEMNNXPQ-UHFFFAOYSA-N 6-amino-3-(4-chlorophenyl)-1-[3-(dimethylamino)propyl]-1-methyl-3H-furo[3,4-c]pyridin-7-ol Chemical compound CN(CCCC1(OC(C=2C=NC(=C(C21)O)N)C2=CC=C(C=C2)Cl)C)C GCZHURKEMNNXPQ-UHFFFAOYSA-N 0.000 description 1
GFEZPGADIMGWOH-UHFFFAOYSA-N 6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical class CC1=NC=C2COCC2=C1O GFEZPGADIMGWOH-UHFFFAOYSA-N 0.000 description 1
RBMJDWDBTDQYHU-UHFFFAOYSA-N 6-methylfuro[3,4-c]pyridine Chemical class CC1=CC=2C(C=N1)=COC=2 RBMJDWDBTDQYHU-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
ULWXXAZYIAWHTF-UHFFFAOYSA-N 7-hydroxy-3-(4-methylphenyl)-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1(=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)C=O)C ULWXXAZYIAWHTF-UHFFFAOYSA-N 0.000 description 1
FQMJBWZGARBBPM-UHFFFAOYSA-N 7-hydroxy-3-methyl-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1=NC(C=O)=C(O)C2=C1C(C)OC2 FQMJBWZGARBBPM-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
SFZWBIOZTWKZHS-UHFFFAOYSA-N 7-hydroxy-3-propyl-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C(CC)C1OCC2=C1C=NC(=C2O)C=O SFZWBIOZTWKZHS-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010002198 Anaphylactic reaction Diseases 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
HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
NTSPGOOJWKAMMV-UHFFFAOYSA-N NC1=C(C2=C(C=N1)COC2C)O Chemical class NC1=C(C2=C(C=N1)COC2C)O NTSPGOOJWKAMMV-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
LCIIOYPBHIZBOD-JMVBYTIWSA-N albonoursin Chemical compound N1C(=O)C(=C/C(C)C)/NC(=O)\C1=C\C1=CC=CC=C1 LCIIOYPBHIZBOD-JMVBYTIWSA-N 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
230000003266 anti-allergic effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
BIRWRIAEWIXFHT-UHFFFAOYSA-N furo[3,4-c]pyridin-7-ol Chemical compound OC1=CN=CC2=COC=C12 BIRWRIAEWIXFHT-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
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
229940126601 medicinal product Drugs 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 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
239000007935 oral tablet 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
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
WIVYTYZCVWHWSH-UHFFFAOYSA-N tert-butyl n-(4-aminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C=C1 WIVYTYZCVWHWSH-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing 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
- 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)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Immunology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

DE19853531747 1984-09-05 1985-09-05 6-aminomethyl-furo-(3,4-c)-pyridinderivate, verfahren zu ihrer herstellung und verbindungen enthaltende arzneimittel Granted DE3531747A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB848422379A GB8422379D0 (en)	1984-09-05	1984-09-05	Derivatives

Publications (2)

Publication Number	Publication Date
DE3531747A1 DE3531747A1 (de)	1986-03-13
DE3531747C2 true DE3531747C2 (no)	1990-09-06

Family

ID=10566274

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19853531747 Granted DE3531747A1 (de)	1984-09-05	1985-09-05	6-aminomethyl-furo-(3,4-c)-pyridinderivate, verfahren zu ihrer herstellung und verbindungen enthaltende arzneimittel

Country Status (23)

Country	Link
JP (1)	JPS6168490A (no)
AT (1)	AT394557B (no)
BE (1)	BE903121A (no)
CA (1)	CA1300150C (no)
CH (1)	CH665642A5 (no)
DE (1)	DE3531747A1 (no)
DK (1)	DK159318C (no)
ES (1)	ES8604966A1 (no)
FI (1)	FI82053C (no)
FR (2)	FR2569699A1 (no)
GB (2)	GB8422379D0 (no)
HK (1)	HK10489A (no)
IE (1)	IE58583B1 (no)
IT (1)	IT1188188B (no)
LU (1)	LU86053A1 (no)
MA (1)	MA20517A1 (no)
MY (1)	MY103211A (no)
NL (1)	NL8502412A (no)
NO (1)	NO160143C (no)
OA (1)	OA08157A (no)
PT (1)	PT81087B (no)
SE (1)	SE461394B (no)
ZA (1)	ZA856089B (no)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 (no) *	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 IE IE218285A patent/IE58583B1/en not_active IP Right Cessation
- 1985-09-04 NO NO853475A patent/NO160143C/no unknown
- 1985-09-04 DK DK402885A patent/DK159318C/da not_active IP Right Cessation
- 1985-09-04 SE SE8504119A patent/SE461394B/sv not_active IP Right Cessation
- 1985-09-04 PT PT81087A patent/PT81087B/pt not_active IP Right Cessation
- 1985-09-04 ES ES546702A patent/ES8604966A1/es not_active Expired
- 1985-09-05 DE DE19853531747 patent/DE3531747A1/de active Granted
- 1985-09-05 MA MA20743A patent/MA20517A1/fr unknown
- 1985-09-05 IT IT22067/85A patent/IT1188188B/it active
- 1985-09-05 AT AT0260285A patent/AT394557B/de not_active IP Right Cessation
- 1985-09-05 OA OA58672A patent/OA08157A/xx unknown
- 1985-09-05 JP JP60195015A patent/JPS6168490A/ja active Granted
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

Also Published As

Publication number	Publication date
NO160143B (no)	1988-12-05
JPH0314830B2 (no)	1991-02-27
FI82053B (fi)	1990-09-28
PT81087B (pt)	1987-10-20
FI853288L (fi)	1986-03-06
AT394557B (de)	1992-05-11
HK10489A (en)	1989-02-10
GB2164037A (en)	1986-03-12
NL8502412A (nl)	1986-04-01
MY103211A (en)	1993-05-29
DK159318C (da)	1991-03-11
IE58583B1 (en)	1993-10-06
GB8520007D0 (en)	1985-09-18
NO853475L (no)	1986-03-06
IT1188188B (it)	1988-01-07
GB8422379D0 (en)	1984-10-10
CA1300150C (en)	1992-05-05
ES546702A0 (es)	1986-03-01
FR2569699A1 (fr)	1986-03-07
ZA856089B (en)	1986-03-26
BE903121A (fr)	1986-02-26
DE3531747A1 (de)	1986-03-13
IT8522067A0 (it)	1985-09-05
JPS6168490A (ja)	1986-04-08
SE8504119L (sv)	1986-03-06
NO160143C (no)	1989-03-15
FR2569562A1 (fr)	1986-03-07
ATA260285A (de)	1991-10-15
CH665642A5 (fr)	1988-05-31
FI853288A0 (fi)	1985-08-28
FI82053C (fi)	1991-01-10
ES8604966A1 (es)	1986-03-01
DK402885D0 (da)	1985-09-04
DK159318B (da)	1990-10-01
MA20517A1 (fr)	1986-04-01
IE852182L (en)	1986-03-05
LU86053A1 (fr)	1986-02-18
SE8504119D0 (sv)	1985-09-04
DK402885A (da)	1986-03-06
GB2164037B (en)	1988-02-17
SE461394B (sv)	1990-02-12
PT81087A (en)	1985-10-01
OA08157A (fr)	1987-03-31
FR2569562B1 (fr)	1989-02-10

Publication	Publication Date	Title
DE1695556C3 (de)	1981-06-25	3-Alkyl-1,2,3,4,4a,9-hexahydropyrazino[1,2-f]morphanthridinderivate
EP0242851B1 (de)	1990-06-13	N-(2'-Aminophenyl)-benzamid-Derivate, Verfahren zu deren Herstellung und deren Verwendung bei der Bekämpfung neoplastischer Erkrankungen
DE2915318C2 (no)	1990-12-13
DE3011490C2 (no)	1988-12-22
DE3503435C2 (no)	1991-11-07
DE3441975C2 (no)	1990-10-04
DE2504565A1 (de)	1975-08-14	Neue derivate von 1h-imidazo(4,5-c) pyridin-7-carboxylsaeuren und -saeureestern
DD211560A5 (de)	1984-07-18	Verfahren zur herstellung kristalliner benzothiazindioxid-salze
DD202568A5 (de)	1983-09-21	Verfahren zur herstellung wasserloeslicher benzothiazindioxid-salze
EP0105210B1 (de)	1987-03-04	Isochinolinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung
DE2604748A1 (de)	1976-08-19	Aminoderivate von imidazo(4,5-b) pyridinen
EP0621037B1 (de)	1999-07-07	Pyrido-pyrimidindione, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE3141387C2 (no)	1991-05-02
DE3531747C2 (no)	1990-09-06
DE1770163A1 (de)	1972-03-09	Neue Glyzerinester,Verfahren zu ihrer Herstellung und diese Ester enthaltende pharmazeutische Zusammensetzungen
DE2720545A1 (de)	1977-11-10	Neue chinazolinderivate, ihre herstellung und pharmazeutische mittel
DE2815088C2 (de)	1985-07-18	5-Piperazinylsubstituierte Derivate von Pyrido-[2.3-b]benzo[1.5]thiazepin, ihre Herstellung und diese enthaltende pharmazeutische Mittel
DE2434929C2 (de)	1984-09-13	p-Acetylaminophenolester von Phenylsalicylsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2314335A1 (de)	1973-10-11	Neue amide der apovincaminsaeure, deren salze, herstellung und medikamente, die diese enthalten
DE3438244C2 (no)	1990-08-30
DE3019019C2 (no)	1988-12-01
DE3541428A1 (de)	1987-05-27	Neue basisch substituierte pyridinverbindungen, verfahren zu ihrer herstellung, die sie enthaltenden arzneimittel und ihre verwendung
CH644596A5 (de)	1984-08-15	2,6-dimethyl-1,4-dihydropyridin-3,5-dikarbonsaeureester und verfahren zu ihrer herstellung.
DE3337925C2 (de)	1994-11-24	N-(6-Aminopurinyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazin-3-carboxamid-1,1-dioxid, Verfahren zu dessen Herstellung und seine Verwendung
DE2844595A1 (de)	1980-04-30	Acylaminodihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

Legal Events

Date	Code	Title
1987-02-19	8110	Request for examination paragraph 44
1990-09-06	D2	Grant after examination
1991-03-07	8364	No opposition during term of opposition
1999-11-11	8339	Ceased/non-payment of the annual fee