DE3442035A1 - 6-vinyl-furo-(3,4-c)-pyridin-derivate, verfahren zu deren herstellung, und diese enthaltende pharmazeutische zusammensetzung - Google Patents
6-vinyl-furo-(3,4-c)-pyridin-derivate, verfahren zu deren herstellung, und diese enthaltende pharmazeutische zusammensetzungInfo
- Publication number
- DE3442035A1 DE3442035A1 DE19843442035 DE3442035A DE3442035A1 DE 3442035 A1 DE3442035 A1 DE 3442035A1 DE 19843442035 DE19843442035 DE 19843442035 DE 3442035 A DE3442035 A DE 3442035A DE 3442035 A1 DE3442035 A1 DE 3442035A1
- Authority
- DE
- Germany
- Prior art keywords
- furo
- groups
- dihydro
- carbon atoms
- group
- Prior art date
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- JYNVFJZLBWIXBQ-UHFFFAOYSA-N 6-ethenylfuro[3,4-c]pyridine Chemical class C1=NC(C=C)=CC2=COC=C21 JYNVFJZLBWIXBQ-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 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 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 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 2
- 108091033409 CRISPR Proteins 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 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
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000006413 ring segment Chemical group 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
- 102100033070 Histone acetyltransferase KAT6B Human genes 0.000 claims 1
- 101000944174 Homo sapiens Histone acetyltransferase KAT6B Proteins 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 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
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 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 2
- -1 7-benzoxy-furo- (3,4-c) pyridine Chemical compound 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000029142 excretion Effects 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 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
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AGMXYLZHFJRHPC-UHFFFAOYSA-N 1-methyl-7-phenylmethoxyfuro[3,4-c]pyridine Chemical compound CC=1OC=C2C=NC=C(C21)OCC2=CC=CC=C2 AGMXYLZHFJRHPC-UHFFFAOYSA-N 0.000 description 1
- ICWXMOFJDWRMFA-UHFFFAOYSA-N 1-methylfuro[3,4-c]pyridin-7-ol Chemical compound CC=1OC=C2C=NC=C(C21)O ICWXMOFJDWRMFA-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
- 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
- WVSSCFLXTJYQQK-UHFFFAOYSA-N 6-(chloromethyl)-3-(4-chlorophenyl)-3-ethyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound C=1C=C(Cl)C=CC=1C1(CC)OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 WVSSCFLXTJYQQK-UHFFFAOYSA-N 0.000 description 1
- ASCKJMZNZOULFH-UHFFFAOYSA-N 6-(chloromethyl)-3-(4-chlorophenyl)-3-methyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound C=1C=C(Cl)C=CC=1C1(C)OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 ASCKJMZNZOULFH-UHFFFAOYSA-N 0.000 description 1
- KTLAFBRMBJFHMH-UHFFFAOYSA-N 6-(chloromethyl)-3-(4-fluorophenyl)-3-methyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine Chemical compound C=1C=C(F)C=CC=1C1(C)OCC2=C1C=NC(CCl)=C2OCC1=CC=CC=C1 KTLAFBRMBJFHMH-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- PHJBISJMBQUNIK-UHFFFAOYSA-N [3-(4-chlorophenyl)-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridin-6-yl]methanol Chemical compound OCC1=NC=C2C(C=3C=CC(Cl)=CC=3)OCC2=C1OCC1=CC=CC=C1 PHJBISJMBQUNIK-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 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
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- BIRWRIAEWIXFHT-UHFFFAOYSA-N furo[3,4-c]pyridin-7-ol Chemical compound OC1=CN=CC2=COC=C12 BIRWRIAEWIXFHT-UHFFFAOYSA-N 0.000 description 1
- GJVNMIQVQXYJCP-UHFFFAOYSA-N furo[3,4-c]pyridine Chemical compound C1=NC=CC2=[C]OC=C21 GJVNMIQVQXYJCP-UHFFFAOYSA-N 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000004172 nitrogen cycle Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000010992 reflux Methods 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000003424 uricosuric effect Effects 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838330517A GB8330517D0 (en) | 1983-11-16 | 1983-11-16 | 6-vinyl-furo-(3,4-c)pyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3442035A1 true DE3442035A1 (de) | 1985-05-30 |
Family
ID=10551816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843442035 Ceased DE3442035A1 (de) | 1983-11-16 | 1984-11-16 | 6-vinyl-furo-(3,4-c)-pyridin-derivate, verfahren zu deren herstellung, und diese enthaltende pharmazeutische zusammensetzung |
Country Status (25)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT394557B (de) * | 1984-09-05 | 1992-05-11 | Scras | Verfahren zur herstellung neuer 6-aminomethyl-furo-(3,4-c)-pyridinderivate |
| AT397093B (de) * | 1988-04-06 | 1994-01-25 | Sod Conseils Rech Applic | Stereospezifisches verfahren für die herstellung von enantiomeren des 3-substituierten furo (3,4-c) pyridins, so erhaltene enantiomere oder mischungen davon sowie diese enthaltene therapeutische mittel |
| DE4115681C2 (de) * | 1990-05-14 | 2003-10-30 | Sod Conseils Rech Applic | Verfahren zur Herstellung von Furo[3,4-c]pyridinderivaten in nicht racemischer Form |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8402740D0 (en) * | 1984-02-02 | 1984-03-07 | Scras | Furo-(3 4-c)-pyridine derivatives |
| GB8917168D0 (en) * | 1989-07-27 | 1989-09-13 | Scras | Asymmetric synthesis of furo(3,4-c)pyridine derivatives |
| EP0511163B1 (de) * | 1991-04-24 | 1995-07-26 | Ciba-Geigy Ag | Fliessfähige wässrige Dispersionen von Polycarbonsäure-Korrosionsinhibitoren |
| JP2002539127A (ja) | 1999-03-08 | 2002-11-19 | メディキュア インコーポレーテッド | ビタミンｂ−６障害のためのピリドキサル類縁体 |
| US6489345B1 (en) | 1999-07-13 | 2002-12-03 | Medicure, Inc. | Treatment of diabetes and related pathologies |
| WO2001013900A2 (en) | 1999-08-24 | 2001-03-01 | Medicure International Inc. | Compositions for the treatment of cardiovascular diseases containing pyridoxal compounds and cardiovascular compounds |
| US7442689B2 (en) * | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| WO2001064692A1 (en) | 2000-02-29 | 2001-09-07 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| AU784840B2 (en) | 2000-03-28 | 2006-07-06 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US6897228B2 (en) * | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| JP2004502757A (ja) | 2000-07-07 | 2004-01-29 | 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 | ピリドキシンおよびピリドキサール類縁体：心血管系治療薬 |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel 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 |
| CA2570048A1 (en) * | 2004-07-07 | 2006-01-12 | Medicure International Inc. | Combination therapies employing platelet aggregation drugs |
| US20070060549A1 (en) * | 2004-08-10 | 2007-03-15 | Friesen Albert D | Combination therapies employing ace inhibitors and uses thereof for the treatment of diabetic disorders |
| US20060094749A1 (en) * | 2004-10-28 | 2006-05-04 | Medicure International Inc. | Substituted pyridoxines as anti-platelet agents |
| US7459468B2 (en) * | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| CA2585165A1 (en) * | 2004-10-28 | 2006-05-18 | Medicure International Inc. | Dual antiplatelet/anticoagulant pyridoxine analogs |
| JP2009517411A (ja) * | 2005-11-28 | 2009-04-30 | メディキュア インターナショナル インコーポレーテッド | 心血管及び関連病状の処置のための調剤 |
| CN116365023B (zh) * | 2021-12-23 | 2026-04-03 | 宁德国泰华荣新材料有限公司 | 一种锂离子电池电解液及使用该电解液的锂离子电池 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2850948A1 (de) * | 1977-11-25 | 1979-05-31 | Scras | Pyridinderivat, verfahren zu seiner herstellung und arzneimittel |
| DE3204596A1 (de) * | 1981-02-10 | 1982-09-09 | Société de Conseils de Recherches et d'Applications Scientifiques S.A., 75008 Paris | Furo-(3,4-c)-pyridinderivate, verfahren zu deren herstellung und diese enthaltende therapeutische zusammensetzung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2008582B (en) * | 1977-11-25 | 1982-04-28 | Scras | Pyridine derivative |
-
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 MA MA20483A patent/MA20259A1/fr unknown
- 1984-11-01 FI FI844279A patent/FI79852C/fi not_active IP Right Cessation
- 1984-11-01 JP JP59229029A patent/JPS60112793A/ja active Granted
- 1984-11-05 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 IT IT8423565A patent/IT1213246B/it active
- 1984-11-14 DZ DZ847328A patent/DZ701A1/fr active
- 1984-11-14 SE SE8405710A patent/SE458116B/sv not_active IP Right Cessation
- 1984-11-14 CA CA000467828A patent/CA1257271A/en not_active Expired
- 1984-11-15 DK DK542584A patent/DK157870C/da not_active IP Right Cessation
- 1984-11-15 IE IE2930/84A patent/IE58005B1/en not_active IP Right Cessation
- 1984-11-15 ES ES537665A patent/ES8600299A1/es not_active Expired
- 1984-11-16 PT PT79511A patent/PT79511B/pt not_active IP Right Cessation
- 1984-11-16 OA OA58441A patent/OA07864A/xx unknown
- 1984-11-16 FR FR8417481A patent/FR2554719B1/fr not_active Expired
- 1984-11-16 DE DE19843442035 patent/DE3442035A1/de not_active Ceased
- 1984-11-16 AT AT0364384A patent/AT391867B/de not_active IP Right Cessation
- 1984-11-16 FR FR8417480A patent/FR2554817B1/fr not_active Expired
-
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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2850948A1 (de) * | 1977-11-25 | 1979-05-31 | Scras | Pyridinderivat, verfahren zu seiner herstellung und arzneimittel |
| DE3204596A1 (de) * | 1981-02-10 | 1982-09-09 | Société de Conseils de Recherches et d'Applications Scientifiques S.A., 75008 Paris | Furo-(3,4-c)-pyridinderivate, verfahren zu deren herstellung und diese enthaltende therapeutische zusammensetzung |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT394557B (de) * | 1984-09-05 | 1992-05-11 | Scras | Verfahren zur herstellung neuer 6-aminomethyl-furo-(3,4-c)-pyridinderivate |
| AT397093B (de) * | 1988-04-06 | 1994-01-25 | Sod Conseils Rech Applic | Stereospezifisches verfahren für die herstellung von enantiomeren des 3-substituierten furo (3,4-c) pyridins, so erhaltene enantiomere oder mischungen davon sowie diese enthaltene therapeutische mittel |
| DE4115681C2 (de) * | 1990-05-14 | 2003-10-30 | Sod Conseils Rech Applic | Verfahren zur Herstellung von Furo[3,4-c]pyridinderivaten in nicht racemischer Form |
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