CA1221969A - 3-methylflavone-8-carboxylic acid esters - Google Patents
3-methylflavone-8-carboxylic acid estersInfo
- Publication number
- CA1221969A CA1221969A CA000406549A CA406549A CA1221969A CA 1221969 A CA1221969 A CA 1221969A CA 000406549 A CA000406549 A CA 000406549A CA 406549 A CA406549 A CA 406549A CA 1221969 A CA1221969 A CA 1221969A
- Authority
- CA
- Canada
- Prior art keywords
- pharmaceutically acceptable
- methylflavone
- carboxylate
- addition salts
- acid addition
- 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.)
- Expired
Links
- KMMBBZOSQNLLMN-UHFFFAOYSA-N 3-methylflavone-8-carboxylic acid Chemical class O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 KMMBBZOSQNLLMN-UHFFFAOYSA-N 0.000 title claims abstract description 16
- -1 3--methylflavone-8-carboxylic acid halide Chemical class 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000010992 reflux Methods 0.000 claims abstract description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- GPFVBEXADULZAD-UHFFFAOYSA-N 3-methyl-4-oxo-2-phenylchromene-8-carbonyl chloride Chemical compound O1C2=C(C(Cl)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 GPFVBEXADULZAD-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
- UOIWRLPZDGOIQS-UHFFFAOYSA-N oxiran-2-ylmethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCC1CO1 UOIWRLPZDGOIQS-UHFFFAOYSA-N 0.000 claims description 4
- VQTYZZPDAFGNCK-UHFFFAOYSA-N (2-methyl-1-piperidin-1-ylpropan-2-yl) 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OC(C)(C)CN1CCCCC1 VQTYZZPDAFGNCK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- UXCABTUQGBBPPF-GHMZBOCLSA-N (1r,2r)-2-piperidin-1-ylcyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1N1CCCCC1 UXCABTUQGBBPPF-GHMZBOCLSA-N 0.000 claims description 2
- UKANCZCEGQDKGF-UHFFFAOYSA-N 1-methylpiperidin-3-ol Chemical compound CN1CCCC(O)C1 UKANCZCEGQDKGF-UHFFFAOYSA-N 0.000 claims description 2
- SSBJNXYJAHFKJQ-UHFFFAOYSA-N 2-methyl-1-piperidin-1-ylpropan-2-ol Chemical compound CC(C)(O)CN1CCCCC1 SSBJNXYJAHFKJQ-UHFFFAOYSA-N 0.000 claims description 2
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- CKWOBMSBMBOZAI-UHFFFAOYSA-N (1-methylpiperidin-3-yl) 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1N(C)CCCC1OC(=O)C1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O CKWOBMSBMBOZAI-UHFFFAOYSA-N 0.000 claims 2
- RCHXUFKGCSQRAC-UHFFFAOYSA-N (1-phenyl-2-piperidin-1-ylethyl) 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OC(C=1C=CC=CC=1)CN1CCCCC1 RCHXUFKGCSQRAC-UHFFFAOYSA-N 0.000 claims 2
- JATMDXFNBJJFFF-UHFFFAOYSA-N (2-hydroxy-3-piperidin-1-ylpropyl) 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCC(O)CN1CCCCC1 JATMDXFNBJJFFF-UHFFFAOYSA-N 0.000 claims 2
- OUVRQEDIEUQCGG-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound O1C2=C(C(=O)OC3C4CCN(CC4)C3)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 OUVRQEDIEUQCGG-UHFFFAOYSA-N 0.000 claims 2
- VFLQCANTVVGZSX-UHFFFAOYSA-N 3-(2-methylpiperidin-1-yl)propyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound CC1CCCCN1CCCOC(=O)C1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O VFLQCANTVVGZSX-UHFFFAOYSA-N 0.000 claims 2
- VZEMCYIKEZYCQP-UHFFFAOYSA-N 4-piperidin-1-ylbutan-2-yl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C=1C=CC(C(C(C)=C(C=2C=CC=CC=2)O2)=O)=C2C=1C(=O)OC(C)CCN1CCCCC1 VZEMCYIKEZYCQP-UHFFFAOYSA-N 0.000 claims 2
- GQGOMBLXHOGVMK-DNQXCXABSA-N [(1r,2r)-2-piperidin-1-ylcyclohexyl] 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound N1([C@@H]2CCCC[C@H]2OC(=O)C2=C3OC(=C(C(C3=CC=C2)=O)C)C=2C=CC=CC=2)CCCCC1 GQGOMBLXHOGVMK-DNQXCXABSA-N 0.000 claims 2
- QFOXCAYKFUIJRM-UHFFFAOYSA-N [2-methyl-1-(2-methylpiperidin-1-yl)propan-2-yl] 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound CC1CCCCN1CC(C)(C)OC(=O)C1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O QFOXCAYKFUIJRM-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BJEMJLNVSZPUDE-UHFFFAOYSA-N (1-methylpiperidin-4-yl) 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1CN(C)CCC1OC(=O)C1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O BJEMJLNVSZPUDE-UHFFFAOYSA-N 0.000 claims 1
- GVDIQEGOCHYSJA-UHFFFAOYSA-N 1-piperidin-1-ylpropan-2-yl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C=1C=CC(C(C(C)=C(C=2C=CC=CC=2)O2)=O)=C2C=1C(=O)OC(C)CN1CCCCC1 GVDIQEGOCHYSJA-UHFFFAOYSA-N 0.000 claims 1
- FDGQAIQVFCVTRB-UHFFFAOYSA-N 2-(piperidin-1-ylmethyl)cyclohexan-1-ol Chemical compound OC1CCCCC1CN1CCCCC1 FDGQAIQVFCVTRB-UHFFFAOYSA-N 0.000 claims 1
- LLWPAQYHXNBZJB-UHFFFAOYSA-N 2-methyl-1-(2-methylpiperidin-1-yl)propan-2-ol Chemical compound CC1CCCCN1CC(C)(C)O LLWPAQYHXNBZJB-UHFFFAOYSA-N 0.000 claims 1
- JNSUUJLFWBSBME-UHFFFAOYSA-N 3-(2-methylpiperidin-1-yl)propan-1-ol Chemical compound CC1CCCCN1CCCO JNSUUJLFWBSBME-UHFFFAOYSA-N 0.000 claims 1
- XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 claims 1
- ZXAPAKFRWAWSKS-UHFFFAOYSA-N 4-piperidin-1-ylbutan-2-ol Chemical compound CC(O)CCN1CCCCC1 ZXAPAKFRWAWSKS-UHFFFAOYSA-N 0.000 claims 1
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 claims 1
- QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 claims 1
- MGAAJWBLHHAPFS-UHFFFAOYSA-N [2-(piperidin-1-ylmethyl)cyclohexyl] 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OC1CCCCC1CN1CCCCC1 MGAAJWBLHHAPFS-UHFFFAOYSA-N 0.000 claims 1
- 150000001414 amino alcohols Chemical class 0.000 claims 1
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 11
- 230000000903 blocking effect Effects 0.000 abstract description 5
- 239000011575 calcium Substances 0.000 abstract description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052791 calcium Inorganic materials 0.000 abstract description 4
- 150000002212 flavone derivatives Chemical class 0.000 abstract description 4
- 239000000376 reactant Substances 0.000 abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 3
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 229940124326 anaesthetic agent Drugs 0.000 abstract description 2
- 230000003444 anaesthetic effect Effects 0.000 abstract description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 210000000626 ureter Anatomy 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- SPIUTQOUKAMGCX-UHFFFAOYSA-N flavoxate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCN1CCCCC1 SPIUTQOUKAMGCX-UHFFFAOYSA-N 0.000 description 3
- 229960000855 flavoxate Drugs 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000050 smooth muscle relaxant Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 241000244155 Taenia Species 0.000 description 2
- 230000001663 anti-spastic effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ASWRTDCDFPALAX-PAFGHYSMSA-N (1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol;hydrochloride Chemical compound Cl.C1C(O)C[C@H]2CC[C@@H]1N2C ASWRTDCDFPALAX-PAFGHYSMSA-N 0.000 description 1
- HXHURGCIBJMJDF-UHFFFAOYSA-N 1-(2-chloro-2-phenylethyl)piperidine Chemical compound C=1C=CC=CC=1C(Cl)CN1CCCCC1 HXHURGCIBJMJDF-UHFFFAOYSA-N 0.000 description 1
- BYCSEPVPVJSDKS-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;hydrochloride Chemical compound Cl.O1C2=C(C(=O)OC3C4CCN(CC4)C3)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 BYCSEPVPVJSDKS-UHFFFAOYSA-N 0.000 description 1
- RJFNAVZRPRUWIJ-UHFFFAOYSA-N 3-(2-methylpiperidin-1-yl)propyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;hydrochloride Chemical compound Cl.CC1CCCCN1CCCOC(=O)C1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O RJFNAVZRPRUWIJ-UHFFFAOYSA-N 0.000 description 1
- LPACBRAWRCXZGB-UHFFFAOYSA-N 3-methyl-2-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 LPACBRAWRCXZGB-UHFFFAOYSA-N 0.000 description 1
- LRTSDXDGOFQRSW-UHFFFAOYSA-N 4-oxo-2-phenylchromene-8-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C(C=2)=O)=C1OC=2C1=CC=CC=C1 LRTSDXDGOFQRSW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YBKSHVOJUMUFDS-KZDWWKKTSA-N [(1r,2s)-2-piperidin-1-ylcyclohexyl] 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;hydrochloride Chemical compound Cl.N1([C@H]2CCCC[C@H]2OC(=O)C2=C3OC(=C(C(C3=CC=C2)=O)C)C=2C=CC=CC=2)CCCCC1 YBKSHVOJUMUFDS-KZDWWKKTSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8122158 | 1981-07-17 | ||
| GB8122158 | 1981-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1221969A true CA1221969A (en) | 1987-05-19 |
Family
ID=10523330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000406549A Expired CA1221969A (en) | 1981-07-17 | 1982-07-05 | 3-methylflavone-8-carboxylic acid esters |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4550115A (en, 2012) |
| EP (1) | EP0072620B1 (en, 2012) |
| JP (1) | JPS5835185A (en, 2012) |
| KR (1) | KR870000275B1 (en, 2012) |
| AR (1) | AR231543A1 (en, 2012) |
| AT (1) | ATE16806T1 (en, 2012) |
| AU (1) | AU553322B2 (en, 2012) |
| CA (1) | CA1221969A (en, 2012) |
| DE (1) | DE3267782D1 (en, 2012) |
| DK (1) | DK160498C (en, 2012) |
| ES (1) | ES8400109A1 (en, 2012) |
| FI (1) | FI73677C (en, 2012) |
| GB (1) | GB2104507B (en, 2012) |
| GR (1) | GR81300B (en, 2012) |
| HU (1) | HU189601B (en, 2012) |
| IE (1) | IE53525B1 (en, 2012) |
| IL (1) | IL66187A0 (en, 2012) |
| IT (1) | IT1198389B (en, 2012) |
| NO (1) | NO157330C (en, 2012) |
| NZ (1) | NZ200981A (en, 2012) |
| PH (1) | PH18001A (en, 2012) |
| PT (1) | PT75230B (en, 2012) |
| SG (1) | SG77784G (en, 2012) |
| YU (2) | YU136682A (en, 2012) |
| ZA (1) | ZA824335B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58225083A (ja) * | 1982-06-23 | 1983-12-27 | Nippon Shinyaku Co Ltd | メチルフラボン誘導体 |
| FI74707C (fi) * | 1982-06-29 | 1988-03-10 | Sandoz Ag | Foerfarande foer framstaellning av terapeutiskt anvaendbara alkylenoeverbryggade piperidylestrar eller -amider av bicykliska karboxylsyror. |
| IT1229856B (it) * | 1989-04-20 | 1991-09-13 | Recordati Chem Pharm | Compresse a rilascio controllato contenenti flavossato. |
| US5474994A (en) * | 1992-05-26 | 1995-12-12 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 -adrenergic and 5HT1A |
| US5605896A (en) * | 1992-02-25 | 1997-02-25 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 adrenergic and 5HT1A activities |
| SG65570A1 (en) | 1992-02-25 | 1999-06-22 | Recordati Chem Pharm | Heterobicyclic compounds |
| IT1254469B (it) * | 1992-02-25 | 1995-09-25 | Recordati Chem Pharm | Derivati benzopiranici e benzotiopiranici |
| IT1258315B (it) * | 1992-04-10 | 1996-02-22 | Recordati Chem Pharm | Derivati del flavone |
| US6087366A (en) * | 1996-03-07 | 2000-07-11 | The Trustees Of Columbia University In The City Of New York | Use of flavopiridol or a pharmaceutically acceptable salt thereof for inhibiting cell damage or cell death |
| US7501443B2 (en) | 2002-12-23 | 2009-03-10 | Ranbaxy Laboratories Limited | Flavaxate derivatives as muscarinic receptor antagonists |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2921070A (en) * | 1957-11-05 | 1960-01-12 | Recordati Lab Farmacologico S | Basic esters of 3-methylflavone-8-carboxylic acid |
| US4217351A (en) * | 1976-08-04 | 1980-08-12 | Abbott Laboratories | Benzopyrano quinuclidines useful as antiglaucoma agents |
-
1982
- 1982-06-16 NZ NZ200981A patent/NZ200981A/en unknown
- 1982-06-18 GB GB08217744A patent/GB2104507B/en not_active Expired
- 1982-06-18 ZA ZA824335A patent/ZA824335B/xx unknown
- 1982-06-23 YU YU01366/82A patent/YU136682A/xx unknown
- 1982-06-24 NO NO822127A patent/NO157330C/no unknown
- 1982-06-29 AR AR289821A patent/AR231543A1/es active
- 1982-07-01 IL IL66187A patent/IL66187A0/xx not_active IP Right Cessation
- 1982-07-05 CA CA000406549A patent/CA1221969A/en not_active Expired
- 1982-07-06 DK DK301982A patent/DK160498C/da not_active IP Right Cessation
- 1982-07-07 IT IT22274/82A patent/IT1198389B/it active
- 1982-07-09 DE DE8282303634T patent/DE3267782D1/de not_active Expired
- 1982-07-09 AT AT82303634T patent/ATE16806T1/de not_active IP Right Cessation
- 1982-07-09 EP EP82303634A patent/EP0072620B1/en not_active Expired
- 1982-07-12 PT PT75230A patent/PT75230B/pt not_active IP Right Cessation
- 1982-07-12 IE IE1678/82A patent/IE53525B1/en not_active IP Right Cessation
- 1982-07-12 PH PH27559A patent/PH18001A/en unknown
- 1982-07-12 US US06/397,196 patent/US4550115A/en not_active Expired - Fee Related
- 1982-07-13 FI FI822493A patent/FI73677C/fi not_active IP Right Cessation
- 1982-07-14 JP JP57123732A patent/JPS5835185A/ja active Granted
- 1982-07-15 ES ES513993A patent/ES8400109A1/es not_active Expired
- 1982-07-15 GR GR68773A patent/GR81300B/el unknown
- 1982-07-16 HU HU822322A patent/HU189601B/hu not_active IP Right Cessation
- 1982-07-16 AU AU86098/82A patent/AU553322B2/en not_active Ceased
- 1982-07-16 KR KR8203175A patent/KR870000275B1/ko not_active Expired
-
1984
- 1984-07-16 YU YU01251/84A patent/YU125184A/xx unknown
- 1984-11-02 SG SG777/84A patent/SG77784G/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |