CS198190B2 - Způsob výroby nových 2-piperidinoalkyl-l,4-b3nzodioxanů - Google Patents
Způsob výroby nových 2-piperidinoalkyl-l,4-b3nzodioxanů Download PDFInfo
- Publication number
- CS198190B2 CS198190B2 CS411376A CS411376A CS198190B2 CS 198190 B2 CS198190 B2 CS 198190B2 CS 411376 A CS411376 A CS 411376A CS 411376 A CS411376 A CS 411376A CS 198190 B2 CS198190 B2 CS 198190B2
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- Czechoslovakia
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- carbon atoms
- compounds
- integer
- hydroxy
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- 238000000034 method Methods 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- -1 hydroxy, methoxy, ethoxy Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical compound C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 235000002639 sodium chloride Nutrition 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000282693 Cercopithecidae Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000035939 shock Effects 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000036407 pain Effects 0.000 description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- IZDQKYKYHYKLRG-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-3-yl)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1OC2=CC=CC=C2OC1 IZDQKYKYHYKLRG-UHFFFAOYSA-N 0.000 description 2
- XHQRVJPQGSRKMK-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-2-yl)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1OC2=CC=CC=C2C1 XHQRVJPQGSRKMK-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
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
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- 230000000701 neuroleptic effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
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- 229910052623 talc Inorganic materials 0.000 description 2
- BPQIARYKBUADJY-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(2,3-dihydro-1,4-benzodioxin-3-yl)ethyl]-4-ethoxy-4-phenylpiperidine Chemical compound OC(=O)\C=C/C(O)=O.C1CN(CCC2OC3=CC=CC=C3OC2)CCC1(OCC)C1=CC=CC=C1 BPQIARYKBUADJY-BTJKTKAUSA-N 0.000 description 1
- QAWRUQMKWRUBJZ-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-4-phenylpiperidin-4-ol Chemical compound C1CN(CC2OC3=CC=CC=C3OC2)CCC1(O)C1=CC=CC=C1 QAWRUQMKWRUBJZ-UHFFFAOYSA-N 0.000 description 1
- OOOYFRRIUZGPOU-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1,4-benzodioxin-3-yl)ethyl]-4-[2-(4-fluorophenyl)ethyl]piperidine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1CCC1CCN(CCC2OC3=CC=CC=C3OC2)CC1 OOOYFRRIUZGPOU-UHFFFAOYSA-N 0.000 description 1
- SBJGMUOIXKNSEK-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1,4-benzodioxin-3-yl)ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCC2OC3=CC=CC=C3OC2)CCC1(O)C1=CC=CC=C1 SBJGMUOIXKNSEK-UHFFFAOYSA-N 0.000 description 1
- SNUVNAGRMXWMNF-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1,4-benzodioxin-3-yl)ethyl]-4-pyridin-2-ylpiperidin-4-ol;dihydrochloride Chemical compound Cl.Cl.C1CN(CCC2OC3=CC=CC=C3OC2)CCC1(O)C1=CC=CC=N1 SNUVNAGRMXWMNF-UHFFFAOYSA-N 0.000 description 1
- RWJYJUNHUZJEOT-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1-benzofuran-2-yl)ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCC2OC3=CC=CC=C3C2)CCC1(O)C1=CC=CC=C1 RWJYJUNHUZJEOT-UHFFFAOYSA-N 0.000 description 1
- DSXGISSRCZNZNQ-UHFFFAOYSA-N 1-[3-(2,3-dihydro-1,4-benzodioxin-3-yl)propyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCCC2OC3=CC=CC=C3OC2)CCC1(O)C1=CC=CC=C1 DSXGISSRCZNZNQ-UHFFFAOYSA-N 0.000 description 1
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 1
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical class CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- NHSOOAWURRKYMM-UHFFFAOYSA-N 2,3-dihydro-1,4-benzoxathiine Chemical class C1=CC=C2OCCSC2=C1 NHSOOAWURRKYMM-UHFFFAOYSA-N 0.000 description 1
- NPEFMXMRSFIHKN-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-3-yl)acetic acid Chemical compound C1=CC=C2OC(CC(=O)O)COC2=C1 NPEFMXMRSFIHKN-UHFFFAOYSA-N 0.000 description 1
- PWZFEIJALHLRKF-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-3-yl)acetonitrile Chemical compound C1=CC=C2OC(CC#N)COC2=C1 PWZFEIJALHLRKF-UHFFFAOYSA-N 0.000 description 1
- VRCHCDXHBXLNKZ-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-3-yl)ethanol Chemical compound C1=CC=C2OC(CCO)COC2=C1 VRCHCDXHBXLNKZ-UHFFFAOYSA-N 0.000 description 1
- HKJSLKIPAZEKGM-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-2-yl)acetic acid Chemical compound C1=CC=C2OC(CC(=O)O)CC2=C1 HKJSLKIPAZEKGM-UHFFFAOYSA-N 0.000 description 1
- QQLNIFBCQNGXIQ-UHFFFAOYSA-N 2-(6-methyl-2,3-dihydro-1,4-benzodioxin-3-yl)acetic acid Chemical compound O1CC(CC(O)=O)OC2=CC(C)=CC=C21 QQLNIFBCQNGXIQ-UHFFFAOYSA-N 0.000 description 1
- PDPFIODCZGCNTK-UHFFFAOYSA-N 2-(6-methyl-2,3-dihydro-1,4-benzodioxin-3-yl)ethanol Chemical compound O1CC(CCO)OC2=CC(C)=CC=C21 PDPFIODCZGCNTK-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS78413A CS198193B2 (cs) | 1975-06-23 | 1978-01-20 | Způsob výroby nových 2-piperidinoalkyl-l,4-benžodioxanů |
| CS78411A CS198191B2 (en) | 1975-06-23 | 1978-01-20 | Method of producting new 2-piperidinoalkyl-1,4-benzodioxanes |
| CS78412A CS198192B2 (cs) | 1975-06-23 | 1978-01-20 | Způsob výroby nových 2-piperidínoalky]-l;4-benzodioxanů |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/589,118 US4039676A (en) | 1975-06-23 | 1975-06-23 | 2-piperidinoalkyl-1,4-benzodioxans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS198190B2 true CS198190B2 (cs) | 1980-05-30 |
Family
ID=24356671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS411376A CS198190B2 (cs) | 1975-06-23 | 1976-06-22 | Způsob výroby nových 2-piperidinoalkyl-l,4-b3nzodioxanů |
Country Status (13)
| Country | Link |
|---|---|
| CS (1) | CS198190B2 (de) |
| DD (1) | DD126408A5 (de) |
| DK (1) | DK278976A (de) |
| ES (4) | ES449069A1 (de) |
| FI (1) | FI761818A7 (de) |
| GR (1) | GR60557B (de) |
| HU (1) | HU174277B (de) |
| IE (1) | IE43244B1 (de) |
| IL (1) | IL49863A0 (de) |
| NO (1) | NO762158L (de) |
| NZ (1) | NZ181241A (de) |
| PT (1) | PT65229B (de) |
| ZA (2) | ZA762264B (de) |
-
1976
- 1976-04-14 ZA ZA762264A patent/ZA762264B/xx unknown
- 1976-06-16 PT PT6522976A patent/PT65229B/pt unknown
- 1976-06-21 GR GR51055A patent/GR60557B/el unknown
- 1976-06-21 ES ES449069A patent/ES449069A1/es not_active Expired
- 1976-06-22 ZA ZA00763705A patent/ZA763705B/xx unknown
- 1976-06-22 CS CS411376A patent/CS198190B2/cs unknown
- 1976-06-22 IL IL49863A patent/IL49863A0/xx unknown
- 1976-06-22 NO NO762158A patent/NO762158L/no unknown
- 1976-06-22 DD DD19350376A patent/DD126408A5/xx unknown
- 1976-06-22 HU HU76CI1670A patent/HU174277B/hu unknown
- 1976-06-22 IE IE134376A patent/IE43244B1/en unknown
- 1976-06-22 NZ NZ18124176A patent/NZ181241A/xx unknown
- 1976-06-22 DK DK278976A patent/DK278976A/da unknown
- 1976-06-22 FI FI761818A patent/FI761818A7/fi not_active Application Discontinuation
-
1977
- 1977-07-13 ES ES460695A patent/ES460695A1/es not_active Expired
- 1977-07-13 ES ES460694A patent/ES460694A1/es not_active Expired
- 1977-07-13 ES ES460696A patent/ES460696A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE43244B1 (en) | 1981-01-14 |
| PT65229A (en) | 1976-07-01 |
| NO762158L (de) | 1976-12-27 |
| FI761818A7 (de) | 1976-12-24 |
| IE43244L (en) | 1976-12-23 |
| PT65229B (en) | 1977-11-23 |
| ZA762264B (en) | 1977-04-27 |
| DK278976A (da) | 1976-12-24 |
| ES460696A1 (es) | 1978-07-01 |
| ES449069A1 (es) | 1977-11-16 |
| ZA763705B (en) | 1978-02-22 |
| ES460695A1 (es) | 1978-05-01 |
| GR60557B (en) | 1978-06-22 |
| HU174277B (hu) | 1979-12-28 |
| ES460694A1 (es) | 1978-05-16 |
| DD126408A5 (de) | 1977-07-13 |
| NZ181241A (en) | 1978-04-03 |
| IL49863A0 (en) | 1976-08-31 |
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