DK142055B - Analogifremgangsmåde til fremstilling af 1,3-dihydrospiro(isobenzofuraner) eller syreadditionssalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af 1,3-dihydrospiro(isobenzofuraner) eller syreadditionssalte deraf. Download PDFInfo
- Publication number
- DK142055B DK142055B DK645074AA DK645074A DK142055B DK 142055 B DK142055 B DK 142055B DK 645074A A DK645074A A DK 645074AA DK 645074 A DK645074 A DK 645074A DK 142055 B DK142055 B DK 142055B
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- isobenzofuran
- dihydrospiro
- cycloazalkane
- hydroxy
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 8
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical class C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- -1 methylenedioxy Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000007818 Grignard reagent Substances 0.000 claims description 9
- 150000004795 grignard reagents Chemical class 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 238000007363 ring formation reaction Methods 0.000 claims description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 150000002641 lithium Chemical class 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- JTXAETLSYPFRJX-UHFFFAOYSA-N [Li]C1=C(C=CC=C1)C=1OCCN1 Chemical compound [Li]C1=C(C=CC=C1)C=1OCCN1 JTXAETLSYPFRJX-UHFFFAOYSA-N 0.000 claims description 2
- QANZRMGXJSNJQN-UHFFFAOYSA-N [Li]C1=C(COCC2=C(C=CC=C2)[Li])C=CC=C1.[Li] Chemical compound [Li]C1=C(COCC2=C(C=CC=C2)[Li])C=CC=C1.[Li] QANZRMGXJSNJQN-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 150000002918 oxazolines Chemical class 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- 239000013078 crystal Substances 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000012280 lithium aluminium hydride Substances 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 125000003003 spiro group Chemical group 0.000 description 7
- XLCYXINIUJNTPF-UHFFFAOYSA-N 2-(2-bromophenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2C(=CC=CC=2)Br)=N1 XLCYXINIUJNTPF-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 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 5
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 5
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229940035676 analgesics Drugs 0.000 description 4
- 239000000730 antalgic agent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- RNMPNVBLQHYANU-UHFFFAOYSA-N spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC21CCNCC2 RNMPNVBLQHYANU-UHFFFAOYSA-N 0.000 description 4
- AJECYOIWECOTAK-UHFFFAOYSA-N 1'-methylspiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C1CN(C)CCC21C1=CC=CC=C1C(=O)O2 AJECYOIWECOTAK-UHFFFAOYSA-N 0.000 description 3
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 3
- HMTFLSDATQBMHT-UHFFFAOYSA-N 2-chloro-1-(4-fluorophenyl)butan-1-one;ethene Chemical group C=C.CCC(Cl)C(=O)C1=CC=C(F)C=C1 HMTFLSDATQBMHT-UHFFFAOYSA-N 0.000 description 3
- LQNFAGZUHQSKFT-UHFFFAOYSA-N 4-[2-(hydroxymethyl)phenyl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CC=CC=C1CO LQNFAGZUHQSKFT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- BYOIMOJOKVUNTP-UHFFFAOYSA-N spiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C12=CC=CC=C2COC21CCNCC2 BYOIMOJOKVUNTP-UHFFFAOYSA-N 0.000 description 3
- 239000003204 tranquilizing agent Substances 0.000 description 3
- 230000002936 tranquilizing effect Effects 0.000 description 3
- NNCNIXZKXXUHRQ-UHFFFAOYSA-N 1'-(2-phenylethyl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(CC1)CCN1CCC1=CC=CC=C1 NNCNIXZKXXUHRQ-UHFFFAOYSA-N 0.000 description 2
- DJYFEXWVCWVUJH-UHFFFAOYSA-N 1'-(cyclopropanecarbonyl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CCN1C(=O)C1CC1 DJYFEXWVCWVUJH-UHFFFAOYSA-N 0.000 description 2
- ILOMMMNNLDJQCU-UHFFFAOYSA-N 1'-acetylspiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C1CN(C(=O)C)CCC21C1=CC=CC=C1C(=O)O2 ILOMMMNNLDJQCU-UHFFFAOYSA-N 0.000 description 2
- NQCPWIBLOQTVAP-UHFFFAOYSA-N 1'-benzylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3CO2)CCN1CC1=CC=CC=C1 NQCPWIBLOQTVAP-UHFFFAOYSA-N 0.000 description 2
- DZVDLNBMBMYHGT-UHFFFAOYSA-N 1'-methylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1CN(C)CCC21C1=CC=CC=C1CO2 DZVDLNBMBMYHGT-UHFFFAOYSA-N 0.000 description 2
- MLOWDNZWSWEGMA-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-spiro[1h-2-benzofuran-3,4'-piperidine]-1'-ylbutan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C3=CC=CC=C3CO2)CC1 MLOWDNZWSWEGMA-UHFFFAOYSA-N 0.000 description 2
- UXXLTPGCINZEFM-UHFFFAOYSA-N 1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(CCCCl)C1=CC=C(F)C=C1 UXXLTPGCINZEFM-UHFFFAOYSA-N 0.000 description 2
- OHNMYFOLDDPTQR-UHFFFAOYSA-N 1-benzyl-3-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]piperidin-3-ol Chemical compound CC1(C)COC(C=2C(=CC=CC=2)C2(O)CN(CC=3C=CC=CC=3)CCC2)=N1 OHNMYFOLDDPTQR-UHFFFAOYSA-N 0.000 description 2
- VRRMNBLSWBBBHD-UHFFFAOYSA-N 1-benzyl-3-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]pyrrolidin-3-ol Chemical compound CC1(C)COC(C=2C(=CC=CC=2)C2(O)CN(CC=3C=CC=CC=3)CC2)=N1 VRRMNBLSWBBBHD-UHFFFAOYSA-N 0.000 description 2
- MGEGQMSBUDAOJA-UHFFFAOYSA-N 1-benzyl-4-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]piperidin-4-ol Chemical compound CC1(C)COC(C=2C(=CC=CC=2)C2(O)CCN(CC=3C=CC=CC=3)CC2)=N1 MGEGQMSBUDAOJA-UHFFFAOYSA-N 0.000 description 2
- MRHQANLLSOTFKB-UHFFFAOYSA-N 1-butyl-4-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]piperidin-4-ol Chemical compound C1CN(CCCC)CCC1(O)C1=CC=CC=C1C1=NC(C)(C)CO1 MRHQANLLSOTFKB-UHFFFAOYSA-N 0.000 description 2
- GUOXCQSGCVGOIL-UHFFFAOYSA-N 1-ethyl-4-[2-(hydroxymethyl)phenyl]piperidin-4-ol Chemical compound C1CN(CC)CCC1(O)C1=CC=CC=C1CO GUOXCQSGCVGOIL-UHFFFAOYSA-N 0.000 description 2
- ILZYXPIIYMNWEE-UHFFFAOYSA-N 2-(2-bromo-4,5-dimethoxyphenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound C1=C(OC)C(OC)=CC(Br)=C1C1=NC(C)(C)CO1 ILZYXPIIYMNWEE-UHFFFAOYSA-N 0.000 description 2
- MKLPVCPLEZZAQM-UHFFFAOYSA-N 2-(2-bromo-5-methoxyphenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound COC1=CC=C(Br)C(C=2OCC(C)(C)N=2)=C1 MKLPVCPLEZZAQM-UHFFFAOYSA-N 0.000 description 2
- LMMMAMQFBVGSSV-UHFFFAOYSA-N 2-bromo-n-(1-hydroxy-2-methylpropan-2-yl)-4,5-dimethoxybenzamide Chemical compound COC1=CC(Br)=C(C(=O)NC(C)(C)CO)C=C1OC LMMMAMQFBVGSSV-UHFFFAOYSA-N 0.000 description 2
- YXLYUMKNPBVOKB-UHFFFAOYSA-N 2-bromo-n-(1-hydroxy-2-methylpropan-2-yl)-5-methoxybenzamide Chemical compound COC1=CC=C(Br)C(C(=O)NC(C)(C)CO)=C1 YXLYUMKNPBVOKB-UHFFFAOYSA-N 0.000 description 2
- LMFNTOPITQZOCK-UHFFFAOYSA-N 2-chloro-4-fluoro-n-(1-hydroxy-2-methylpropan-2-yl)benzamide Chemical compound OCC(C)(C)NC(=O)C1=CC=C(F)C=C1Cl LMFNTOPITQZOCK-UHFFFAOYSA-N 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- ODZAKGBCCCWUBT-UHFFFAOYSA-N 4-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]-1-(2-phenylethyl)piperidin-4-ol Chemical compound CC1(C)COC(C=2C(=CC=CC=2)C2(O)CCN(CCC=3C=CC=CC=3)CC2)=N1 ODZAKGBCCCWUBT-UHFFFAOYSA-N 0.000 description 2
- QORHELIFDRVNPI-UHFFFAOYSA-N 6-bromo-n-(1-hydroxy-2-methylpropan-2-yl)-1,3-benzodioxole-5-carboxamide Chemical compound C1=C(Br)C(C(=O)NC(C)(CO)C)=CC2=C1OCO2 QORHELIFDRVNPI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- TZVXKRQCQSKVAY-UHFFFAOYSA-N spiro[2-benzofuran-3,3'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC21CCCNC2 TZVXKRQCQSKVAY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- IOWGHQGLUMEZKG-UHFFFAOYSA-N (2-bromophenyl)methanol Chemical compound OCC1=CC=CC=C1Br IOWGHQGLUMEZKG-UHFFFAOYSA-N 0.000 description 1
- CPIXUPDASCPXET-UHFFFAOYSA-N 1'-(3-oxo-3-phenylpropyl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CCN1CCC(=O)C1=CC=CC=C1 CPIXUPDASCPXET-UHFFFAOYSA-N 0.000 description 1
- NSATVGINZOGFAM-UHFFFAOYSA-N 1'-(cyclopropylmethyl)spiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3CO2)CCN1CC1CC1 NSATVGINZOGFAM-UHFFFAOYSA-N 0.000 description 1
- SIQDXHZYYJAKLH-UHFFFAOYSA-N 1'-[4,4-bis(4-fluorophenyl)butyl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC2(C3=CC=CC=C3C(=O)O2)CC1 SIQDXHZYYJAKLH-UHFFFAOYSA-N 0.000 description 1
- QOWYAZGBNNEQOA-UHFFFAOYSA-N 1'-benzyl-5,6-dimethoxyspiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C1=2C=C(OC)C(OC)=CC=2C(=O)OC1(CC1)CCN1CC1=CC=CC=C1 QOWYAZGBNNEQOA-UHFFFAOYSA-N 0.000 description 1
- RZXNEAPKBXXMQP-UHFFFAOYSA-N 1'-benzylspiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(CC1)CCN1CC1=CC=CC=C1 RZXNEAPKBXXMQP-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- MMSLMJHFKNLANL-UHFFFAOYSA-N 1-benzyl-4-[2-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-4,5-dimethoxyphenyl]piperidin-4-ol Chemical compound C1CN(CC=2C=CC=CC=2)CCC1(O)C=1C=C(OC)C(OC)=CC=1C1=NC(C)(C)CO1 MMSLMJHFKNLANL-UHFFFAOYSA-N 0.000 description 1
- DHGMDHQNUNRMIN-UHFFFAOYSA-N 1-benzylpyrrolidin-3-one Chemical compound C1C(=O)CCN1CC1=CC=CC=C1 DHGMDHQNUNRMIN-UHFFFAOYSA-N 0.000 description 1
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
- OCNWYKFGWLGNHZ-UHFFFAOYSA-N 1-butylpiperidin-4-one Chemical compound CCCCN1CCC(=O)CC1 OCNWYKFGWLGNHZ-UHFFFAOYSA-N 0.000 description 1
- SKXKZDUTELKKAV-UHFFFAOYSA-N 2-(6-bromo-1,3-benzodioxol-5-yl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2C(=CC=3OCOC=3C=2)Br)=N1 SKXKZDUTELKKAV-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- UCEXMJMSILZCHZ-UHFFFAOYSA-N 2-[(4-butoxybenzoyl)amino]acetic acid Chemical compound CCCCOC1=CC=C(C(=O)NCC(O)=O)C=C1 UCEXMJMSILZCHZ-UHFFFAOYSA-N 0.000 description 1
- DILISPNYIVRDBP-UHFFFAOYSA-N 2-[3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]-2-naphthalen-2-ylimidazol-4-yl]acetonitrile Chemical compound OC(CNC1=NC=CC(=N1)N1C(=NC=C1CC#N)C1=CC2=CC=CC=C2C=C1)C DILISPNYIVRDBP-UHFFFAOYSA-N 0.000 description 1
- 125000006197 2-benzoyl ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])([H])C([H])([H])* 0.000 description 1
- QADMMVWIMLEMOU-UHFFFAOYSA-N 2-bromo-4,5-dimethoxybenzoyl chloride Chemical compound COC1=CC(Br)=C(C(Cl)=O)C=C1OC QADMMVWIMLEMOU-UHFFFAOYSA-N 0.000 description 1
- RZCQJXVXRYIJQE-UHFFFAOYSA-N 2-bromo-5-methoxybenzoyl chloride Chemical compound COC1=CC=C(Br)C(C(Cl)=O)=C1 RZCQJXVXRYIJQE-UHFFFAOYSA-N 0.000 description 1
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- POIAZJJVWRVLBO-UHFFFAOYSA-N 2-chloro-4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(Cl)=C1 POIAZJJVWRVLBO-UHFFFAOYSA-N 0.000 description 1
- QMNXJNURJISYMS-UHFFFAOYSA-N 3-(dimethylamino)-1-phenylpropan-1-one Chemical compound CN(C)CCC(=O)C1=CC=CC=C1 QMNXJNURJISYMS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OBAJFBHNCQOLOB-UHFFFAOYSA-N 4-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-5-methoxyphenyl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CC(OC)=CC=C1C1=NC(C)(C)CO1 OBAJFBHNCQOLOB-UHFFFAOYSA-N 0.000 description 1
- ICMJMKOIRYHDBC-UHFFFAOYSA-N 4-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CC=CC=C1C1=NC(C)(C)CO1 ICMJMKOIRYHDBC-UHFFFAOYSA-N 0.000 description 1
- RZGAENGFJFRMLS-UHFFFAOYSA-N 6-bromo-1,3-benzodioxole-5-carbonyl chloride Chemical compound C1=C(Br)C(C(=O)Cl)=CC2=C1OCO2 RZGAENGFJFRMLS-UHFFFAOYSA-N 0.000 description 1
- LVOAQCRVNAPOBT-UHFFFAOYSA-N 6-methoxy-1'-methylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C=1C(OC)=CC=C2C=1COC21CCN(C)CC1 LVOAQCRVNAPOBT-UHFFFAOYSA-N 0.000 description 1
- MATVMNOLBQPVEY-UHFFFAOYSA-N 6-methoxy-1'-methylspiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C=1C(OC)=CC=C2C=1C(=O)OC21CCN(C)CC1 MATVMNOLBQPVEY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 206010021118 Hypotonia Diseases 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
- 241001465754 Metazoa Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- RLGKYWLHSNOODU-UHFFFAOYSA-N [Li]C1=CC=CC=C1COCC1=CC=CC=C1[Li] Chemical compound [Li]C1=CC=CC=C1COCC1=CC=CC=C1[Li] RLGKYWLHSNOODU-UHFFFAOYSA-N 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000000159 acid neutralizing agent Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000037396 body weight Effects 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
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 229940056913 eftilagimod alfa Drugs 0.000 description 1
- OXLXKYYXGYHBII-UHFFFAOYSA-N ethyl 3-oxospiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21C1=CC=CC=C1C(=O)O2 OXLXKYYXGYHBII-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- YDJXNYNKKXZBMP-UHFFFAOYSA-N n-phenethyl-4-piperidinone Chemical compound C1CC(=O)CCN1CCC1=CC=CC=C1 YDJXNYNKKXZBMP-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940065347 propoxyphene hydrochloride Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D491/10—Spiro-condensed systems
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42408073 | 1973-12-12 | ||
| US05/424,080 US3962259A (en) | 1973-12-12 | 1973-12-12 | 1,3-Dihydrospiro[isobenzofuran]s and derivatives thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK645074A DK645074A (en, 2012) | 1975-08-18 |
| DK142055B true DK142055B (da) | 1980-08-18 |
| DK142055C DK142055C (en, 2012) | 1981-01-12 |
Family
ID=23681366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK645074AA DK142055B (da) | 1973-12-12 | 1974-12-11 | Analogifremgangsmåde til fremstilling af 1,3-dihydrospiro(isobenzofuraner) eller syreadditionssalte deraf. |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US3962259A (en, 2012) |
| JP (1) | JPS5089363A (en, 2012) |
| AT (2) | AT352125B (en, 2012) |
| BE (1) | BE823279A (en, 2012) |
| CA (1) | CA1051886A (en, 2012) |
| CH (2) | CH620214A5 (en, 2012) |
| DE (1) | DE2458176A1 (en, 2012) |
| DK (1) | DK142055B (en, 2012) |
| FR (1) | FR2254332B1 (en, 2012) |
| GB (1) | GB1495286A (en, 2012) |
| IE (1) | IE40297B1 (en, 2012) |
| IL (1) | IL46202A (en, 2012) |
| LU (1) | LU71460A1 (en, 2012) |
| NL (1) | NL7415940A (en, 2012) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4241071A (en) * | 1977-01-27 | 1980-12-23 | American Hoechst Corporation | Antidepressant (α-phenyl-2-tolyl)azacycloalkanes |
| US4166119A (en) * | 1978-04-14 | 1979-08-28 | American Hoechst Corporation | Analgesic and tranquilizing spiro[dihydrobenzofuran]piperidines and pyrrolidines |
| US4166120A (en) * | 1978-04-14 | 1979-08-28 | American Hoechst Corporation | Analgesic and tranquilizing benzoylpropyl-spiro[dihydrobenzofuran]piperidines and pyrrolidines |
| US4301292A (en) * | 1979-09-06 | 1981-11-17 | Hoechst-Roussel Pharmaceuticals, Incorporated | 1-[2-(4,5-Dihydro-4,4-dialkyl-2-oxazolyl)phenyl]-4-(dialkylamino)cyclohexanol |
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| FR2498603A1 (fr) * | 1981-01-29 | 1982-07-30 | Delalande Sa | Nouveaux derives spiro-1 isobenzofuranniques et spiro-1 isobenzothiopheniques, leur procede de preparation et leur application en therapeutique |
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| WO1995028389A1 (fr) * | 1994-04-15 | 1995-10-26 | Yamanouchi Pharmaceutical Co., Ltd. | Compose spiro et composition medicinale issue de ce compose |
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| KR20080098070A (ko) * | 2006-02-22 | 2008-11-06 | 버텍스 파마슈티칼스 인코포레이티드 | 무스카린성 수용체의 조절제로서의 스피로 축합된 피페리딘 |
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| WO2008021375A2 (en) * | 2006-08-15 | 2008-02-21 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
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Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686186A (en) * | 1970-10-05 | 1972-08-22 | William J Houlihan | Substituted isochroman or phthalan piperidenes |
-
1973
- 1973-12-12 US US05/424,080 patent/US3962259A/en not_active Expired - Lifetime
-
1974
- 1974-12-06 NL NL7415940A patent/NL7415940A/xx not_active Application Discontinuation
- 1974-12-06 IL IL46202A patent/IL46202A/xx unknown
- 1974-12-09 DE DE19742458176 patent/DE2458176A1/de not_active Withdrawn
- 1974-12-11 CA CA215,785A patent/CA1051886A/en not_active Expired
- 1974-12-11 DK DK645074AA patent/DK142055B/da unknown
- 1974-12-11 IE IE2547/74A patent/IE40297B1/en unknown
- 1974-12-11 LU LU71460A patent/LU71460A1/xx unknown
- 1974-12-11 AT AT988374A patent/AT352125B/de not_active IP Right Cessation
- 1974-12-11 CH CH1646974A patent/CH620214A5/de not_active IP Right Cessation
- 1974-12-12 JP JP49142998A patent/JPS5089363A/ja active Pending
- 1974-12-12 BE BE151443A patent/BE823279A/xx unknown
- 1974-12-12 GB GB53743/74A patent/GB1495286A/en not_active Expired
- 1974-12-12 FR FR7441007A patent/FR2254332B1/fr not_active Expired
-
1975
- 1975-07-01 US US05/592,214 patent/US3985889A/en not_active Expired - Lifetime
-
1977
- 1977-11-14 AT AT0812377A patent/AT365191B/de not_active IP Right Cessation
-
1979
- 1979-06-26 CH CH596979A patent/CH624407A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK142055C (en, 2012) | 1981-01-12 |
| IL46202A0 (en) | 1975-03-13 |
| NL7415940A (nl) | 1975-06-16 |
| CH624407A5 (en, 2012) | 1981-07-31 |
| DK645074A (en, 2012) | 1975-08-18 |
| AT365191B (de) | 1981-12-28 |
| DE2458176A1 (de) | 1975-06-26 |
| US3962259A (en) | 1976-06-08 |
| FR2254332A1 (en, 2012) | 1975-07-11 |
| JPS5089363A (en, 2012) | 1975-07-17 |
| CH620214A5 (en, 2012) | 1980-11-14 |
| CA1051886A (en) | 1979-04-03 |
| ATA988374A (de) | 1979-02-15 |
| ATA812377A (de) | 1981-05-15 |
| BE823279A (en, 2012) | 1975-06-12 |
| AT352125B (de) | 1979-09-10 |
| US3985889A (en) | 1976-10-12 |
| IE40297B1 (en) | 1979-04-25 |
| IL46202A (en) | 1980-02-29 |
| GB1495286A (en) | 1977-12-14 |
| LU71460A1 (en, 2012) | 1976-11-11 |
| FR2254332B1 (en, 2012) | 1978-07-21 |
| IE40297L (en) | 1975-06-12 |
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