FI76804C - Foerfarande foer framstaellning av farmaceutiskt vaerdefulla 1,3-dihydro-6-metyl-7-hydroxi-furo-(3,4-c)- pyridinderivat. - Google Patents
Foerfarande foer framstaellning av farmaceutiskt vaerdefulla 1,3-dihydro-6-metyl-7-hydroxi-furo-(3,4-c)- pyridinderivat. Download PDFInfo
- Publication number
- FI76804C FI76804C FI841273A FI841273A FI76804C FI 76804 C FI76804 C FI 76804C FI 841273 A FI841273 A FI 841273A FI 841273 A FI841273 A FI 841273A FI 76804 C FI76804 C FI 76804C
- Authority
- FI
- Finland
- Prior art keywords
- group
- methyl
- compound
- hydroxy
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 7
- 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 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 70
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 150000003333 secondary alcohols Chemical class 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 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 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 150000003839 salts 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
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 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
- 239000000047 product Substances 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 238000000921 elemental analysis Methods 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical group BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 15
- 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 12
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 235000012000 cholesterol Nutrition 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 5
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 208000004880 Polyuria Diseases 0.000 description 4
- 239000002934 diuretic Substances 0.000 description 4
- 229940030606 diuretics Drugs 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical group FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000035619 diuresis Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 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 3
- 229960000356 tienilic acid Drugs 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical group CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 244000144993 groups of animals Species 0.000 description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
- -1 p-trifluoromethylphenyl Chemical group 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- HVKCZUVMQPUWSX-UHFFFAOYSA-N 1-bromo-2,3-dichlorobenzene Chemical group ClC1=CC=CC(Br)=C1Cl HVKCZUVMQPUWSX-UHFFFAOYSA-N 0.000 description 1
- NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 1
- XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
- WVUYYXUATWMVIT-UHFFFAOYSA-N 1-bromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C=C1 WVUYYXUATWMVIT-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
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- OYMCMWPHMPODNK-UHFFFAOYSA-N 2-bromofuran Chemical group BrC1=CC=CO1 OYMCMWPHMPODNK-UHFFFAOYSA-N 0.000 description 1
- KRFFDJKRFIRFEH-UHFFFAOYSA-N 3,3,6-trimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound CC1=NC=C2C(C)(C)OCC2=C1O KRFFDJKRFIRFEH-UHFFFAOYSA-N 0.000 description 1
- NQNMXRKFACZBHE-UHFFFAOYSA-N 3,3-dicyclohexyl-6-methyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C1CCCCC1)C1CCCCC1 NQNMXRKFACZBHE-UHFFFAOYSA-N 0.000 description 1
- DFTORWVLZBVUBP-UHFFFAOYSA-N 3,6-dimethyl-3-[2-(3,4,5-trimethoxyphenyl)ethyl]-1h-furo[3,4-c]pyridin-7-ol Chemical compound COC1=C(OC)C(OC)=CC(CCC2(C)C3=C(C(=C(C)N=C3)O)CO2)=C1 DFTORWVLZBVUBP-UHFFFAOYSA-N 0.000 description 1
- VFROHEFJKCMRAI-UHFFFAOYSA-N 3,6-dimethyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C)C1=CC=CC=C1 VFROHEFJKCMRAI-UHFFFAOYSA-N 0.000 description 1
- UNWZJLKKPLMCDP-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-ethyl-6-methyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound O1CC(C(=C(C)N=C2)O)=C2C1(CC)C1=CC=C(Cl)C=C1 UNWZJLKKPLMCDP-UHFFFAOYSA-N 0.000 description 1
- UWSNGEUFIKQEQC-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-methyl-3-propyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound O1CC(C(=C(C)N=C2)O)=C2C1(CCC)C1=CC=C(Cl)C=C1 UWSNGEUFIKQEQC-UHFFFAOYSA-N 0.000 description 1
- IZVHDCOROBLSOQ-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-methyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C=1C=CC(F)=CC=1)C1=CC=CC=C1 IZVHDCOROBLSOQ-UHFFFAOYSA-N 0.000 description 1
- BICNARNVTJHXFY-UHFFFAOYSA-N 3-[4-(diethylaminomethoxy)phenyl]-6-methyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C1=CC(OCN(CC)CC)=CC=C1C1(C=2C=CC=CC=2)C(C=NC(C)=C2O)=C2CO1 BICNARNVTJHXFY-UHFFFAOYSA-N 0.000 description 1
- BIWJXEPRNRDVPB-UHFFFAOYSA-N 3-bromo-n,n-dimethylpropan-1-amine Chemical group CN(C)CCCBr BIWJXEPRNRDVPB-UHFFFAOYSA-N 0.000 description 1
- XIUDHWARDNZSSX-UHFFFAOYSA-N 3-butyl-3-ethyl-6-methyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C1=NC(C)=C(O)C2=C1C(CCCC)(CC)OC2 XIUDHWARDNZSSX-UHFFFAOYSA-N 0.000 description 1
- FDIQPZUVVXGRLW-UHFFFAOYSA-N 3-ethenyl-6-methyl-3-(4-methylsulfanylphenyl)-1h-furo[3,4-c]pyridin-7-ol Chemical compound C1=CC(SC)=CC=C1C1(C=C)C(C=NC(C)=C2O)=C2CO1 FDIQPZUVVXGRLW-UHFFFAOYSA-N 0.000 description 1
- GAMVKSMSXRAXQC-UHFFFAOYSA-N 3-ethyl-6-methyl-3-propyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C1=NC(C)=C(O)C2=C1C(CCC)(CC)OC2 GAMVKSMSXRAXQC-UHFFFAOYSA-N 0.000 description 1
- UNBLNHMGAFTELR-UHFFFAOYSA-N 4-bromo-N,N-diethyl-3-methoxyaniline Chemical compound C(C)N(C1=CC(=C(C=C1)Br)OC)CC UNBLNHMGAFTELR-UHFFFAOYSA-N 0.000 description 1
- LGAAWMCNBATHDY-UHFFFAOYSA-N 5-(2-chloroethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCCl)=CC(OC)=C1OC LGAAWMCNBATHDY-UHFFFAOYSA-N 0.000 description 1
- MIZMBPVMDKMQQN-UHFFFAOYSA-N 6-methyl-3-(4-methylphenyl)-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C1=CC(C)=CC=C1C1(C=2C=CC=CC=2)C(C=NC(C)=C2O)=C2CO1 MIZMBPVMDKMQQN-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 108010010234 HDL Lipoproteins Proteins 0.000 description 1
- 238000008214 LDL Cholesterol Methods 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000005794 circulatory dysfunction Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 201000005577 familial hyperlipidemia Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 description 1
- 229960004569 indapamide Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 238000005303 weighing 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8309165 | 1983-04-05 | ||
| GB8309165 | 1983-04-05 | ||
| GB838327815A GB8327815D0 (en) | 1983-10-18 | 1983-10-18 | Furo-(3 4-c)-pyridine derivatives |
| GB8327815 | 1983-10-18 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI841273A0 FI841273A0 (fi) | 1984-03-30 |
| FI841273L FI841273L (fi) | 1984-10-06 |
| FI76804B FI76804B (fi) | 1988-08-31 |
| FI76804C true FI76804C (fi) | 1988-12-12 |
Family
ID=26285725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI841273A FI76804C (fi) | 1983-04-05 | 1984-03-30 | Foerfarande foer framstaellning av farmaceutiskt vaerdefulla 1,3-dihydro-6-metyl-7-hydroxi-furo-(3,4-c)- pyridinderivat. |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4581363A (enEXAMPLES) |
| JP (1) | JPS59193888A (enEXAMPLES) |
| KR (1) | KR900005518B1 (enEXAMPLES) |
| AU (1) | AU582113B2 (enEXAMPLES) |
| CA (1) | CA1257269A (enEXAMPLES) |
| CH (1) | CH660191A5 (enEXAMPLES) |
| DE (1) | DE3412885C2 (enEXAMPLES) |
| DK (1) | DK157931C (enEXAMPLES) |
| DZ (1) | DZ629A1 (enEXAMPLES) |
| EG (1) | EG18150A (enEXAMPLES) |
| ES (1) | ES8601998A1 (enEXAMPLES) |
| FI (1) | FI76804C (enEXAMPLES) |
| FR (2) | FR2543956B1 (enEXAMPLES) |
| GR (1) | GR79577B (enEXAMPLES) |
| HK (1) | HK11187A (enEXAMPLES) |
| IE (1) | IE57424B1 (enEXAMPLES) |
| IL (1) | IL71243A (enEXAMPLES) |
| IN (1) | IN160104B (enEXAMPLES) |
| IT (1) | IT1173770B (enEXAMPLES) |
| LU (1) | LU85262A1 (enEXAMPLES) |
| MA (1) | MA20084A1 (enEXAMPLES) |
| MX (1) | MX167397B (enEXAMPLES) |
| MY (1) | MY8600664A (enEXAMPLES) |
| NL (1) | NL190328C (enEXAMPLES) |
| NO (1) | NO161802C (enEXAMPLES) |
| NZ (1) | NZ207552A (enEXAMPLES) |
| OA (1) | OA07699A (enEXAMPLES) |
| PT (1) | PT78361B (enEXAMPLES) |
| SE (1) | SE458362B (enEXAMPLES) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| 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 |
| US6043259A (en) * | 1998-07-09 | 2000-03-28 | Medicure Inc. | Treatment of cardiovascular and related pathologies |
| BR0008857A (pt) | 1999-03-08 | 2001-12-18 | Medicure Inc | Análogos de piridoxal para distúrbios da vitaminab-6 |
| EP1196171A2 (en) | 1999-07-13 | 2002-04-17 | Medicure Inc. | Use of pyridoxin derivatives for the treatment of diabetes and related complications |
| CA2383252A1 (en) * | 1999-08-24 | 2001-03-01 | Medicure International Inc. | Treatment of cardiovascular related pathologies |
| US7442689B2 (en) * | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| ES2305994T3 (es) | 2000-02-29 | 2008-11-01 | Medicure International Inc. | Fosfonatos cardioprotectores. |
| US6586414B2 (en) | 2000-03-28 | 2003-07-01 | Medicure International Inc. | Treatment of cerebrovascular disease |
| CA2414188A1 (en) | 2000-07-07 | 2002-01-17 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: cardiovascular therapeutics |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel uses |
| US6897228B2 (en) * | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new 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 |
| AU2005259735A1 (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 |
| JP2008517956A (ja) * | 2004-10-28 | 2008-05-29 | 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 | 二重の抗血小板性／抗凝固性ピリドキシン類似体 |
| US7459468B2 (en) * | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| WO2007059631A1 (en) * | 2005-11-28 | 2007-05-31 | Medicure International Inc. | Selected dosage for the treatment of cardiovascular and related pathologies |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2008582B (en) * | 1977-11-25 | 1982-04-28 | Scras | Pyridine derivative |
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
| IN156817B (enEXAMPLES) * | 1981-02-10 | 1985-11-09 | Scras |
-
1984
- 1984-03-13 IN IN229/DEL/84A patent/IN160104B/en unknown
- 1984-03-14 IL IL71243A patent/IL71243A/xx not_active IP Right Cessation
- 1984-03-19 GR GR74143A patent/GR79577B/el unknown
- 1984-03-19 NZ NZ207552A patent/NZ207552A/en unknown
- 1984-03-21 LU LU85262A patent/LU85262A1/fr unknown
- 1984-03-21 CH CH1419/84A patent/CH660191A5/fr not_active IP Right Cessation
- 1984-03-26 US US06/593,700 patent/US4581363A/en not_active Expired - Lifetime
- 1984-03-28 FR FR8404806A patent/FR2543956B1/fr not_active Expired
- 1984-03-28 FR FR8404807A patent/FR2543829B1/fr not_active Expired
- 1984-03-30 NL NLAANVRAGE8401013,A patent/NL190328C/xx not_active IP Right Cessation
- 1984-03-30 FI FI841273A patent/FI76804C/fi not_active IP Right Cessation
- 1984-04-01 DZ DZ847143A patent/DZ629A1/fr active
- 1984-04-02 MA MA20305A patent/MA20084A1/fr unknown
- 1984-04-03 SE SE8401841A patent/SE458362B/sv not_active IP Right Cessation
- 1984-04-03 EG EG221/84A patent/EG18150A/xx active
- 1984-04-03 PT PT78361A patent/PT78361B/pt not_active IP Right Cessation
- 1984-04-04 IE IE826/84A patent/IE57424B1/en not_active IP Right Cessation
- 1984-04-04 DK DK178084A patent/DK157931C/da not_active IP Right Cessation
- 1984-04-04 MX MX008342A patent/MX167397B/es unknown
- 1984-04-04 NO NO841322A patent/NO161802C/no unknown
- 1984-04-04 AU AU26401/84A patent/AU582113B2/en not_active Ceased
- 1984-04-04 ES ES531285A patent/ES8601998A1/es not_active Expired
- 1984-04-04 KR KR1019840001772A patent/KR900005518B1/ko not_active Expired
- 1984-04-05 CA CA000451348A patent/CA1257269A/en not_active Expired
- 1984-04-05 OA OA58272A patent/OA07699A/xx unknown
- 1984-04-05 DE DE843412885A patent/DE3412885C2/de not_active Expired - Lifetime
- 1984-04-05 JP JP59066853A patent/JPS59193888A/ja active Granted
- 1984-04-05 IT IT20396/84A patent/IT1173770B/it active
-
1986
- 1986-12-30 MY MY664/86A patent/MY8600664A/xx unknown
-
1987
- 1987-02-05 HK HK111/87A patent/HK11187A/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI76804C (fi) | Foerfarande foer framstaellning av farmaceutiskt vaerdefulla 1,3-dihydro-6-metyl-7-hydroxi-furo-(3,4-c)- pyridinderivat. | |
| FI75347C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla furo-(3,4-c)-pyridinderivat. | |
| US4735950A (en) | Furo-(3,4-C)-pyridine derivatives and therapeutic composition containing the same | |
| NL8403353A (nl) | Nieuwe 6-vinyl-furo-(3,4-c)-pyridinederivaten, hun bereiding en farmaceutische preparaten die ze bevatten. | |
| KR860001602B1 (ko) | 피리딘 유도체의 제조방법 | |
| EP0171739A1 (en) | Imidazo[1,5-a]pyrimidine derivatives and process for their preparation | |
| US4497814A (en) | 2-(Pyridinyl)-1,2,4-triazolo[1,5-a]pyrimidines and derivatives useful in increasing cardiac contractility | |
| CS226020B2 (en) | Method of preparing pyridine and pyrimidine derivatives | |
| JP2726999B2 (ja) | イミダゾ［２，１−ｂ］ベンゾチアゾール誘導体及び該化合物を有効成分とする抗潰瘍剤 | |
| US4081449A (en) | Heterocyclic esters of alkylphenyl benzopyranopyridines | |
| GB2154583A (en) | pyrimidobenzthiazoles | |
| US4929616A (en) | Novel basic-substituted 5-halo-thienoisothiazol-3(2H)-one 1,1-dioxides, a process for the preparation thereof, and pharmaceutical preparations containing these compounds | |
| GB2137618A (en) | Furo-(3,4-c)-pyridine derivatives | |
| EP0045473B1 (en) | A pharmaceutical composition containing a benzofuran-carboxamide derivative as the active ingredient | |
| HU193360B (en) | Process for producing /amino-pyridinyl/- and /nitro-pyridinyl/-amino-phenyl/-aryl-methanone derivatives | |
| JPH03148284A (ja) | ジヒドロピリミドチアジン誘導体、それを主成分とする抗炎症剤等製剤組成物、その製造の際の中間体、およびそれらの製造方法 | |
| US4128648A (en) | Substituted pyrano[4,3-d]-thiazolo[3,2-a]pyrimidines | |
| JPH05279255A (ja) | 尿酸排泄促進剤 | |
| HU201330B (en) | Process for producing new thieno (3',4'-4,5)imidazo(2,1-b)thiazole derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SOCIETE DE CONSEILS DE RECHERCHES ET |