HU185088B - Process for preparing 1,3-dihydeo-6-methyl-7-hydroxy-furo/3,4-c-/-pyridine derivatives - Google Patents
Process for preparing 1,3-dihydeo-6-methyl-7-hydroxy-furo/3,4-c-/-pyridine derivatives Download PDFInfo
- Publication number
- HU185088B HU185088B HU82405A HU40582A HU185088B HU 185088 B HU185088 B HU 185088B HU 82405 A HU82405 A HU 82405A HU 40582 A HU40582 A HU 40582A HU 185088 B HU185088 B HU 185088B
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- compound
- hydroxy
- group
- carbon atoms
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 abstract description 46
- 238000002360 preparation method Methods 0.000 abstract description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 17
- 238000000034 method Methods 0.000 abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 7
- 239000011777 magnesium Substances 0.000 abstract description 7
- 229910052749 magnesium Inorganic materials 0.000 abstract description 7
- 239000011674 pyridoxal Substances 0.000 abstract description 7
- 229960003581 pyridoxal Drugs 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract description 2
- 239000011677 pyridoxine Substances 0.000 abstract description 2
- 238000007363 ring formation reaction Methods 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- 229940011671 vitamin b6 Drugs 0.000 abstract description 2
- 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 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 abstract 1
- 229910052731 fluorine Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000000921 elemental analysis Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 10
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- -1 (p-chlorophenyl) -6-methyl-7-hydroxy-furo (3,4-c) pyridine hydrochloride Chemical compound 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 239000002934 diuretic Substances 0.000 description 5
- 229940030606 diuretics Drugs 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 235000008164 pyridoxal Nutrition 0.000 description 5
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 description 2
- 229960000356 tienilic acid Drugs 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- LUNUTDXQTSGSJG-LFABVHOISA-N (2S)-2-amino-2-cyclohexyl-N-(1-diphenoxyphosphorylethyl)acetamide Chemical compound C1([C@H](N)C(=O)NC(C)P(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)CCCCC1 LUNUTDXQTSGSJG-LFABVHOISA-N 0.000 description 1
- NXSVXDCNLSWHME-FUBQLUNQSA-N (2S)-2-amino-N-(1-diphenoxyphosphorylethyl)-3-(1H-imidazol-5-yl)propanamide Chemical compound C([C@H](N)C(=O)NC(C)P(=O)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)C1=CN=CN1 NXSVXDCNLSWHME-FUBQLUNQSA-N 0.000 description 1
- BLSRGJPGRJBHQK-BUSXIPJBSA-N (2s)-2-amino-1-(2-diphenoxyphosphorylpyrrolidin-1-yl)propan-1-one Chemical compound C[C@H](N)C(=O)N1CCCC1P(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 BLSRGJPGRJBHQK-BUSXIPJBSA-N 0.000 description 1
- NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical group FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 1
- YEUYZNNBXLMFCW-UHFFFAOYSA-N 1-bromo-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(Br)C=C1 YEUYZNNBXLMFCW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- LTTRHFRVNMLHBT-UHFFFAOYSA-N 2-(2-bromophenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=CC=C1Br LTTRHFRVNMLHBT-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VFKIQINEAKWHGO-UHFFFAOYSA-N 4-methylbenzoyl bromide Chemical compound CC1=CC=C(C(Br)=O)C=C1 VFKIQINEAKWHGO-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010009192 Circulatory collapse Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- YDWKSSWZGXRQET-UHFFFAOYSA-N Pyrrolidine, 1-[2-(4-bromophenoxy)ethyl]- Chemical compound C1=CC(Br)=CC=C1OCCN1CCCC1 YDWKSSWZGXRQET-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
- 229920002472 Starch Polymers 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002497 iodine compounds Chemical group 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 206010040560 shock Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- ITRBOGBMPGNZBO-AJRGADBESA-N undulifoline Chemical compound C1OCC[C@@H]2[C@H]3N(C)CC[C@@H]2[C@]1(C(=O)OC)C1=C3C2=CC=CC=C2N1 ITRBOGBMPGNZBO-AJRGADBESA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8104072 | 1981-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185088B true HU185088B (en) | 1984-11-28 |
Family
ID=10519587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU82405A HU185088B (en) | 1981-02-10 | 1982-02-10 | Process for preparing 1,3-dihydeo-6-methyl-7-hydroxy-furo/3,4-c-/-pyridine derivatives |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4383998A (en, 2012) |
| JP (1) | JPS57150688A (en, 2012) |
| KR (1) | KR870000206B1 (en, 2012) |
| AR (1) | AR230284A1 (en, 2012) |
| AU (1) | AU545876B2 (en, 2012) |
| BE (1) | BE891797A (en, 2012) |
| CA (1) | CA1175837A (en, 2012) |
| CH (1) | CH649554A5 (en, 2012) |
| DE (1) | DE3204596A1 (en, 2012) |
| DK (1) | DK157551C (en, 2012) |
| DZ (1) | DZ376A1 (en, 2012) |
| ES (1) | ES8302714A1 (en, 2012) |
| FI (1) | FI75347C (en, 2012) |
| FR (2) | FR2499406A1 (en, 2012) |
| GB (1) | GB2092586B (en, 2012) |
| GR (1) | GR75905B (en, 2012) |
| HK (1) | HK22485A (en, 2012) |
| HU (1) | HU185088B (en, 2012) |
| IE (1) | IE52376B1 (en, 2012) |
| IL (1) | IL64759A (en, 2012) |
| IN (1) | IN156817B (en, 2012) |
| IT (1) | IT1157252B (en, 2012) |
| LU (1) | LU83886A1 (en, 2012) |
| MA (1) | MA19378A1 (en, 2012) |
| MX (1) | MX6983E (en, 2012) |
| NL (1) | NL186697C (en, 2012) |
| NO (1) | NO156373C (en, 2012) |
| NZ (1) | NZ199528A (en, 2012) |
| OA (1) | OA07003A (en, 2012) |
| PT (1) | PT74408B (en, 2012) |
| SE (1) | SE456994B (en, 2012) |
| SG (1) | SG85384G (en, 2012) |
| YU (1) | YU44000B (en, 2012) |
| ZA (1) | ZA82158B (en, 2012) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN160104B (en, 2012) * | 1983-04-05 | 1987-06-27 | Scras | |
| US4735950A (en) * | 1983-04-05 | 1988-04-05 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S) | Furo-(3,4-C)-pyridine derivatives and therapeutic composition containing the same |
| GB8327817D0 (en) * | 1983-10-18 | 1983-11-16 | Scras | 4-halo-furo-(3 4-c)-pyridine derivatives |
| GB8330517D0 (en) * | 1983-11-16 | 1983-12-21 | Scras | 6-vinyl-furo-(3,4-c)pyridine derivatives |
| GB8330658D0 (en) * | 1983-11-17 | 1983-12-29 | Scras | 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives |
| GB8402740D0 (en) * | 1984-02-02 | 1984-03-07 | Scras | Furo-(3 4-c)-pyridine derivatives |
| GB8414559D0 (en) * | 1984-06-07 | 1984-07-11 | Scras | Pyridine derivatives |
| GB8422379D0 (en) * | 1984-09-05 | 1984-10-10 | Scras | Derivatives |
| GB8427218D0 (en) * | 1984-10-27 | 1984-12-05 | Scras | Pyridine derivatives |
| DE3519693A1 (de) * | 1985-06-01 | 1987-01-02 | Basf Ag | Pyridin-derivate, ihre herstellung und verwendung |
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| DE3990349T1 (de) * | 1988-04-06 | 1990-04-26 | Scras | Stereospezifisches verfahren zur herstellung von enantiomeren von furo(3,4-c)pyridin, so erhaltene verbindungen und therapeutische zusammensetzungen auf basis dieser verbindungen |
| GB8907480D0 (en) * | 1989-04-03 | 1989-05-17 | Scaras Societe De Conseils De | Separation of insomers of furo(3,4-c)pyridine derivatives |
| GB8917168D0 (en) * | 1989-07-27 | 1989-09-13 | Scras | Asymmetric synthesis of furo(3,4-c)pyridine derivatives |
| US5130252A (en) * | 1990-05-14 | 1992-07-14 | Synthetech, Inc. | Resolution of furopyridine enantiomers and synthetic precursors thereof |
| GB0221494D0 (en) * | 2002-09-16 | 2002-10-23 | Generics Uk Ltd | Novel processes for the preparation of 1.3-dihydro-6-methylfuro (3,4-c) pyndin derivatives |
| HUP0300990A2 (hu) * | 2003-04-15 | 2005-05-30 | SynoSens Kutató és Fejlesztő Kft. | Szinergista gyógyszer-kombináció a diabetesz megelőzésére vagy kezelésére |
| US20060089374A1 (en) * | 2003-07-17 | 2006-04-27 | Glenn Cornett | Enantiomeric compositions of cicletanine, alone and in combination with other agents, for the treatment of disease |
| US20050043391A1 (en) * | 2003-07-17 | 2005-02-24 | Fong Benson M. | Combination therapies for treatment of hypertension and complications in patients with diabetes or metabolic syndrome |
| CA2581337A1 (en) * | 2004-09-22 | 2006-03-30 | Glenn Cornett | Enantiomeric compositions of cicletanine, alone and in combination with other agents, for the treatment of disease |
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| US20060154959A1 (en) * | 2005-01-13 | 2006-07-13 | Navitas Pharma | Combination therapies of cicletanine and carvedilol |
| US20070141174A1 (en) * | 2005-01-13 | 2007-06-21 | Navitas Pharma, Inc. | Enantiomeric compositions of cicletanine, in combination with other agents, for the treatment of hypertension |
| US20080096915A1 (en) * | 2005-01-13 | 2008-04-24 | Greenberg Traurig LLP | Compositions for the treatment of metabolic disorders |
| US20070105817A1 (en) * | 2005-11-09 | 2007-05-10 | Jim Page | Use of cicletanine and other furopyridines for treatment of systolic-predominant hypertension, isolated systolic hypertension, elevated pulse pressure, and general hypertension |
| US20080312241A1 (en) * | 2007-01-03 | 2008-12-18 | Gilead Sciences, Inc. | Cicletanine and PKC inhibitors in the treatment of pulmonary and cardiac disorders |
| AR073259A1 (es) * | 2008-07-29 | 2010-10-28 | Merck & Co Inc | Derivados de furosemida utiles como diureticos |
| US8214941B2 (en) | 2008-10-02 | 2012-07-10 | Kohler Co. | Slip-fit clamping system for mounting a fitting on a wall |
| US8377911B2 (en) * | 2009-10-09 | 2013-02-19 | Merck Sharp & Dohme Corp. | Diuretics |
| EP2498605B1 (en) * | 2009-10-29 | 2014-08-27 | Merck Sharp & Dohme Corp. | Diuretics |
| US9522138B2 (en) * | 2013-12-31 | 2016-12-20 | Don C. Rockey | Systems, methods, techniques, and compounds in research and treatment of portal hypertension and other conditions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
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| Date | Code | Title | Description |
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| HU90 | Patent valid on 900628 |