FI82468C - Foerfarande foer framstaellning av 1,3-dihydro-6-(1-hydroxi-2-dimetylaminometyl-allyl)-7-hydroxi-furo -(3,4-c)-pyridinderivat. - Google Patents
Foerfarande foer framstaellning av 1,3-dihydro-6-(1-hydroxi-2-dimetylaminometyl-allyl)-7-hydroxi-furo -(3,4-c)-pyridinderivat. Download PDFInfo
- Publication number
- FI82468C FI82468C FI853287A FI853287A FI82468C FI 82468 C FI82468 C FI 82468C FI 853287 A FI853287 A FI 853287A FI 853287 A FI853287 A FI 853287A FI 82468 C FI82468 C FI 82468C
- Authority
- FI
- Finland
- Prior art keywords
- group
- hydroxy
- carbon atoms
- furo
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- -1 amino amino group Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- AVZNLXBMQVKETP-UHFFFAOYSA-M [Br-].CN(C)CC([Mg+])=C Chemical compound [Br-].CN(C)CC([Mg+])=C AVZNLXBMQVKETP-UHFFFAOYSA-M 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 235000013162 Cocos nucifera Nutrition 0.000 claims 1
- 244000060011 Cocos nucifera Species 0.000 claims 1
- JCMUOFQHZLPHQP-UHFFFAOYSA-N L-L-Ophthalmic acid Natural products OC(=O)CNC(=O)C(CC)NC(=O)CCC(N)C(O)=O JCMUOFQHZLPHQP-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- JCMUOFQHZLPHQP-BQBZGAKWSA-N ophthalmic acid Chemical compound OC(=O)CNC(=O)[C@H](CC)NC(=O)CC[C@H](N)C(O)=O JCMUOFQHZLPHQP-BQBZGAKWSA-N 0.000 claims 1
- HVVLQPOCRDLFGA-UHFFFAOYSA-N ophthalmic acid Natural products CCC(NC(=O)C(N)CCC(=O)O)C(=O)NCC(=O)O HVVLQPOCRDLFGA-UHFFFAOYSA-N 0.000 claims 1
- 108010088490 ophthalmic acid Proteins 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000000047 product Substances 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 9
- 229960000317 yohimbine Drugs 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical class N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007858 starting material 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000009132 Catalepsy Diseases 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 206010047853 Waxy flexibility Diseases 0.000 description 2
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 2
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000002896 effect on catalepsy Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate 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
- 238000005406 washing Methods 0.000 description 2
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 2
- FSAIGSHOZKOJHJ-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-ylmethyl)-3,4-dihydro-1h-isoquinoline Chemical compound C1CC2=CC=CC=C2CN1CN1CC2=CC=CC=C2CC1 FSAIGSHOZKOJHJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- BWRYFRVJZRDRFL-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-7-hydroxy-3-phenyl-1H-furo[3,4-c]pyridine-6-carbaldehyde Chemical compound C1(=CC=CC=C1)C1(OCC2=C1C=NC(=C2O)C=O)C2=CC=C(C=C2)OCC BWRYFRVJZRDRFL-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
- 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
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
- 229940000681 5-hydroxytryptophan Drugs 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
- 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
- NJKUKUIJCBTUAG-UHFFFAOYSA-N 7-hydroxy-3-methyl-3-pentyl-1H-furo[3,4-c]pyridine-6-carbaldehyde Chemical compound CC1(OCC2=C1C=NC(=C2O)C=O)CCCCC NJKUKUIJCBTUAG-UHFFFAOYSA-N 0.000 description 1
- LSHYFUDECLDRPE-UHFFFAOYSA-N 7-hydroxy-3-methyl-3-phenyl-1H-furo[3,4-c]pyridine-6-carbaldehyde Chemical compound CC1(OCC2=C1C=NC(=C2O)C=O)C2=CC=CC=C2 LSHYFUDECLDRPE-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 101100489867 Mus musculus Got2 gene Proteins 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- PIPZGJSEDRMUAW-VJDCAHTMSA-N hydron;methyl (1s,15r,18s,19r,20s)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;chloride Chemical compound Cl.C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 PIPZGJSEDRMUAW-VJDCAHTMSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000004172 nitrogen cycle Methods 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229960000949 yohimbine hydrochloride Drugs 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8422029 | 1984-08-31 | ||
| GB848422029A GB8422029D0 (en) | 1984-08-31 | 1984-08-31 | 6-substituted-furo-(3 4-c)-pyridine derivatives |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI853287A0 FI853287A0 (fi) | 1985-08-28 |
| FI853287L FI853287L (fi) | 1986-03-01 |
| FI82468B FI82468B (fi) | 1990-11-30 |
| FI82468C true FI82468C (fi) | 1991-03-11 |
Family
ID=10566078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI853287A FI82468C (fi) | 1984-08-31 | 1985-08-28 | Foerfarande foer framstaellning av 1,3-dihydro-6-(1-hydroxi-2-dimetylaminometyl-allyl)-7-hydroxi-furo -(3,4-c)-pyridinderivat. |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS6160688A (en, 2012) |
| AR (1) | AR241455A1 (en, 2012) |
| AT (1) | AT396590B (en, 2012) |
| BE (1) | BE903122A (en, 2012) |
| CA (1) | CA1300149C (en, 2012) |
| CH (1) | CH666688A5 (en, 2012) |
| DE (1) | DE3531004A1 (en, 2012) |
| DK (1) | DK157871C (en, 2012) |
| ES (1) | ES8604967A1 (en, 2012) |
| FI (1) | FI82468C (en, 2012) |
| FR (1) | FR2569698B1 (en, 2012) |
| GB (2) | GB8422029D0 (en, 2012) |
| HK (1) | HK6189A (en, 2012) |
| IE (1) | IE58522B1 (en, 2012) |
| IT (1) | IT1201459B (en, 2012) |
| LU (1) | LU86052A1 (en, 2012) |
| NL (1) | NL8502324A (en, 2012) |
| NO (1) | NO162071C (en, 2012) |
| OA (1) | OA08088A (en, 2012) |
| PT (1) | PT81054B (en, 2012) |
| SE (1) | SE462218B (en, 2012) |
| ZA (1) | ZA856088B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8427218D0 (en) * | 1984-10-27 | 1984-12-05 | Scras | Pyridine derivatives |
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| DE10323602A1 (de) * | 2003-05-19 | 2004-12-16 | Südzucker AG Mannheim/Ochsenfurt | Hartkaramellen mit geträgerten Farbstoffen |
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 |
| ZA842029B (en) * | 1983-04-05 | 1984-10-31 | Scras | Furo-(3,4-c)-pyridine derivatives preparation thereof and therapeutic compositions containing the same |
| GB2153824B (en) * | 1984-02-02 | 1987-04-01 | Scras | Furo-(3,4-c)-pyridine derivatives |
-
1984
- 1984-08-31 GB GB848422029A patent/GB8422029D0/en active Pending
-
1985
- 1985-08-12 GB GB08520169A patent/GB2163744B/en not_active Expired
- 1985-08-12 ZA ZA856088A patent/ZA856088B/xx unknown
- 1985-08-19 SE SE8503869A patent/SE462218B/sv not_active IP Right Cessation
- 1985-08-20 AR AR85301339A patent/AR241455A1/es active
- 1985-08-22 LU LU86052A patent/LU86052A1/fr unknown
- 1985-08-22 CA CA000489219A patent/CA1300149C/en not_active Expired - Lifetime
- 1985-08-23 CH CH3653/85A patent/CH666688A5/fr not_active IP Right Cessation
- 1985-08-23 NL NL8502324A patent/NL8502324A/nl not_active Application Discontinuation
- 1985-08-26 BE BE0/215502A patent/BE903122A/fr not_active IP Right Cessation
- 1985-08-28 FI FI853287A patent/FI82468C/fi not_active IP Right Cessation
- 1985-08-29 AT AT0252985A patent/AT396590B/de not_active IP Right Cessation
- 1985-08-30 PT PT81054A patent/PT81054B/pt not_active IP Right Cessation
- 1985-08-30 IE IE214385A patent/IE58522B1/en not_active IP Right Cessation
- 1985-08-30 FR FR8512917A patent/FR2569698B1/fr not_active Expired
- 1985-08-30 JP JP60190033A patent/JPS6160688A/ja active Granted
- 1985-08-30 DK DK396085A patent/DK157871C/da not_active IP Right Cessation
- 1985-08-30 OA OA58669A patent/OA08088A/xx unknown
- 1985-08-30 NO NO853418A patent/NO162071C/no unknown
- 1985-08-30 ES ES546590A patent/ES8604967A1/es not_active Expired
- 1985-08-30 DE DE19853531004 patent/DE3531004A1/de active Granted
- 1985-08-30 IT IT22035/85A patent/IT1201459B/it active
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1989
- 1989-01-19 HK HK61/89A patent/HK6189A/xx not_active IP Right Cessation
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Owner name: SOCIETE DE CONSEILS DE RECHERCHES ET D APPLICATION |