CA1087181A - Aminoalkylpyrrolobenzoxazalkanes - Google Patents
AminoalkylpyrrolobenzoxazalkanesInfo
- Publication number
- CA1087181A CA1087181A CA272,556A CA272556A CA1087181A CA 1087181 A CA1087181 A CA 1087181A CA 272556 A CA272556 A CA 272556A CA 1087181 A CA1087181 A CA 1087181A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- carbon atoms
- fluorobenzyl
- pyrrole
- compound
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 57
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 84
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 57
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 51
- UWXIKAZQXAYFPT-UHFFFAOYSA-N 1,4-benzoxazepine Chemical compound O1C=CN=CC2=CC=CC=C12 UWXIKAZQXAYFPT-UHFFFAOYSA-N 0.000 claims description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 22
- -1 aryl chloroformate Chemical compound 0.000 claims description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 20
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 20
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 17
- 239000012312 sodium hydride Substances 0.000 claims description 17
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 16
- UPIMQKDDOWHKGU-UHFFFAOYSA-N 2-chloro-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]ethanone Chemical compound FC1=CC=CC=C1CN1C(C(=O)CCl)=CC=C1 UPIMQKDDOWHKGU-UHFFFAOYSA-N 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 10
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 229910052801 chlorine Chemical group 0.000 claims description 9
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 9
- 239000012279 sodium borohydride Substances 0.000 claims description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 9
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- ZCXLTWVZYXBHJS-UHFFFAOYSA-N 1,2-benzoxazepine Chemical compound O1N=CC=CC2=CC=CC=C12 ZCXLTWVZYXBHJS-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims description 6
- BMEWLJMRNCDJMS-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]pyrrole Chemical compound FC1=CC=CC=C1CN1C=CC=C1 BMEWLJMRNCDJMS-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 6
- 239000007818 Grignard reagent Substances 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 5
- 150000004795 grignard reagents Chemical class 0.000 claims description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005283 haloketone group Chemical group 0.000 claims description 4
- GIUUTTFOHUHCOR-UHFFFAOYSA-N 2-(dimethylamino)-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]ethanone Chemical compound CN(C)CC(=O)C1=CC=CN1CC1=CC=CC=C1F GIUUTTFOHUHCOR-UHFFFAOYSA-N 0.000 claims description 3
- GOWVRMAQMFEGTP-UHFFFAOYSA-N 2-(ethylamino)-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]ethanol Chemical compound CCNCC(O)C1=CC=CN1CC1=CC=CC=C1F GOWVRMAQMFEGTP-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 claims description 3
- OMSPCTDRGBLKEY-UHFFFAOYSA-N 2-(cyclopropylamino)-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]ethanone Chemical compound FC1=CC=CC=C1CN1C(C(=O)CNC2CC2)=CC=C1 OMSPCTDRGBLKEY-UHFFFAOYSA-N 0.000 claims description 2
- JOQAKUYKAREGJC-UHFFFAOYSA-N 2-(dimethylamino)-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]ethanol Chemical compound CN(C)CC(O)C1=CC=CN1CC1=CC=CC=C1F JOQAKUYKAREGJC-UHFFFAOYSA-N 0.000 claims description 2
- LZIXCXKBHUWNCH-UHFFFAOYSA-N 2-(ethylamino)-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]ethanone Chemical compound CCNCC(=O)C1=CC=CN1CC1=CC=CC=C1F LZIXCXKBHUWNCH-UHFFFAOYSA-N 0.000 claims description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 2
- 150000007960 acetonitrile Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- 239000012442 inert solvent Substances 0.000 claims 5
- 229960004592 isopropanol Drugs 0.000 claims 5
- 150000002576 ketones Chemical class 0.000 claims 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- SOFJIEADHUVTRO-UHFFFAOYSA-N 2-(cyclopropylamino)-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]ethanol Chemical compound C=1C=CN(CC=2C(=CC=CC=2)F)C=1C(O)CNC1CC1 SOFJIEADHUVTRO-UHFFFAOYSA-N 0.000 claims 2
- 150000004658 ketimines Chemical class 0.000 claims 2
- LWZYUACNWRVDDJ-UHFFFAOYSA-N 1-benzoxepine Chemical compound O1C=CC=CC2=CC=CC=C12 LWZYUACNWRVDDJ-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 abstract description 5
- 239000003204 tranquilizing agent Substances 0.000 abstract description 5
- 230000002936 tranquilizing effect Effects 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 121
- 239000000203 mixture Substances 0.000 description 69
- 239000000243 solution Substances 0.000 description 69
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- 239000003921 oil Substances 0.000 description 47
- 235000019198 oils Nutrition 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 229910052799 carbon Inorganic materials 0.000 description 19
- 229940076134 benzene Drugs 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 235000002639 sodium chloride Nutrition 0.000 description 17
- 230000000875 corresponding effect Effects 0.000 description 16
- 239000000725 suspension Substances 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000012259 ether extract Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000012458 free base Substances 0.000 description 11
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229940086542 triethylamine Drugs 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 150000003891 oxalate salts Chemical class 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 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 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 235000019502 Orange oil Nutrition 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 239000010502 orange oil Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- LFDGRWDETVOGDT-UHFFFAOYSA-N 1h-pyrrole;hydrochloride Chemical compound Cl.C=1C=CNC=1 LFDGRWDETVOGDT-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 229940125681 anticonvulsant agent Drugs 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- FFWQLZFIMNTUCZ-UHFFFAOYSA-N 1-(bromomethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CBr FFWQLZFIMNTUCZ-UHFFFAOYSA-N 0.000 description 2
- IWSKYJPIWLPRNX-UHFFFAOYSA-N 1-(dimethylamino)-2-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]propan-2-ol Chemical compound CN(C)CC(C)(O)C1=CC=CN1CC1=CC=CC=C1F IWSKYJPIWLPRNX-UHFFFAOYSA-N 0.000 description 2
- MMZYCBHLNZVROM-UHFFFAOYSA-N 1-fluoro-2-methylbenzene Chemical compound CC1=CC=CC=C1F MMZYCBHLNZVROM-UHFFFAOYSA-N 0.000 description 2
- MIDZWBCDTVWAKI-UHFFFAOYSA-N 2-(diethylamino)-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]ethanone Chemical compound CCN(CC)CC(=O)C1=CC=CN1CC1=CC=CC=C1F MIDZWBCDTVWAKI-UHFFFAOYSA-N 0.000 description 2
- RPPMSKCRNMFUQX-UHFFFAOYSA-N 2-anilino-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]ethanol Chemical compound C=1C=CN(CC=2C(=CC=CC=2)F)C=1C(O)CNC1=CC=CC=C1 RPPMSKCRNMFUQX-UHFFFAOYSA-N 0.000 description 2
- NBSAANKQLOYUAO-UHFFFAOYSA-N 2-chloro-1-[1-[(4-chloro-2-fluorophenyl)methyl]pyrrol-2-yl]ethanone Chemical compound FC1=CC(Cl)=CC=C1CN1C(C(=O)CCl)=CC=C1 NBSAANKQLOYUAO-UHFFFAOYSA-N 0.000 description 2
- SFVYUAJWNYVQDB-UHFFFAOYSA-N 2h-1,2-benzoxazocine Chemical compound O1NC=CC=CC2=CC=CC=C21 SFVYUAJWNYVQDB-UHFFFAOYSA-N 0.000 description 2
- KLVKXWMCQFBUFA-UHFFFAOYSA-N 3-(dimethylamino)-1-[1-[(2-fluorophenyl)methyl]pyrrol-2-yl]propan-1-one Chemical compound CN(C)CCC(=O)C1=CC=CN1CC1=CC=CC=C1F KLVKXWMCQFBUFA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229960003299 ketamine Drugs 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229960002523 mercuric chloride Drugs 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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]
-
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US661.505 | 1976-02-26 | ||
| US05/661,505 US4029672A (en) | 1976-02-26 | 1976-02-26 | Aminoalkylpyrrolobenzoxazalkanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087181A true CA1087181A (en) | 1980-10-07 |
Family
ID=24653884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA272,556A Expired CA1087181A (en) | 1976-02-26 | 1977-02-24 | Aminoalkylpyrrolobenzoxazalkanes |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US4029672A (enExample) |
| JP (1) | JPS52125195A (enExample) |
| BE (1) | BE851915A (enExample) |
| CA (1) | CA1087181A (enExample) |
| CH (1) | CH634576A5 (enExample) |
| DE (1) | DE2708111A1 (enExample) |
| DK (1) | DK84077A (enExample) |
| FR (1) | FR2342290A1 (enExample) |
| GB (1) | GB1577342A (enExample) |
| IE (1) | IE45651B1 (enExample) |
| IT (1) | IT1075298B (enExample) |
| LU (1) | LU76838A1 (enExample) |
| NL (1) | NL7701832A (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4029672A (en) * | 1976-02-26 | 1977-06-14 | American Hoechst Corporation | Aminoalkylpyrrolobenzoxazalkanes |
| US4112112A (en) * | 1976-06-29 | 1978-09-05 | Merck & Co., Inc. | Pyrrolo[2,1-b] [3]benzazepines useful for producing a skeletal muscle relaxing or tranquilizing effect |
| US4169095A (en) * | 1977-01-19 | 1979-09-25 | American Hoechst Corporation | Process for preparing aminoalkylpyrrolobenzoxazalkanes |
| US4169094A (en) * | 1977-01-19 | 1979-09-25 | American Hoechst Corporation | Process for preparing aminoalkylpyrrolobenzoxazalkanes |
| US4608374A (en) * | 1983-11-07 | 1986-08-26 | Hoechst-Roussel Pharmaceuticals Inc. | 11-substituted 5H,11H-pyrrolo[2,1-c][1,4]benzoxazepines as antipsychotic and analgesic agents |
| US4681879A (en) * | 1983-11-07 | 1987-07-21 | Hoechst-Roussel Pharmaceuticals Inc. | 11-substituted 5H,11H-pyrrolo[2,1-c][1,4]benzoxazepines as antipsychotic and analgesic agents |
| US4833244A (en) * | 1985-04-22 | 1989-05-23 | Hoechst-Rouseel Pharmaceuticals Inc. | Ethanobenzazepines |
| US4758559A (en) * | 1986-01-21 | 1988-07-19 | Ciba-Geigy Corporation | Pyrrolo[1,2-a] [4,1]benzoxazepine derivatives useful as calmodulin and histamine inhibitors |
| US4865764A (en) * | 1987-07-20 | 1989-09-12 | Hoechst-Roussel Pharmaceuticals, Inc. | 5-aryl-11-substituted-5H,11H-pyrrolo[2,1-][1,4]benzoxazepines as hypotensive agents |
| US5015637A (en) * | 1990-05-25 | 1991-05-14 | Hoechst-Roussel Pharmaceutical Inc. | Pyrido[3,4-b]pyrrolo[1,2-e][1,4,5]oxadiazepines |
| WO1995018092A1 (en) * | 1993-12-28 | 1995-07-06 | Maruho Co., Ltd. | Amino ketone derivative |
| AUPP433398A0 (en) * | 1998-06-25 | 1998-07-16 | Australian National University, The | Compounds and processes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1154744A (en) * | 1966-05-17 | 1969-06-11 | Whitefin Holding Sa | Disubstituted Aminoethanols |
| JPS4812756B1 (enExample) * | 1970-12-25 | 1973-04-23 | ||
| BE795451A (fr) * | 1972-02-23 | 1973-08-16 | Pfizer | Agents hypoglycemiants aza indoliques tricycliques |
| US4053599A (en) * | 1976-02-26 | 1977-10-11 | American Hoechst Corporation | Piperazionalkylpyrrolobenzoxazalkanes |
| US4029672A (en) * | 1976-02-26 | 1977-06-14 | American Hoechst Corporation | Aminoalkylpyrrolobenzoxazalkanes |
-
1976
- 1976-02-26 US US05/661,505 patent/US4029672A/en not_active Expired - Lifetime
-
1977
- 1977-01-19 US US05/760,507 patent/US4107074A/en not_active Expired - Lifetime
- 1977-01-19 US US05/760,509 patent/US4107187A/en not_active Expired - Lifetime
- 1977-02-21 NL NL7701832A patent/NL7701832A/xx not_active Application Discontinuation
- 1977-02-24 LU LU76838A patent/LU76838A1/xx unknown
- 1977-02-24 CA CA272,556A patent/CA1087181A/en not_active Expired
- 1977-02-24 FR FR7705370A patent/FR2342290A1/fr active Granted
- 1977-02-24 IT IT20659/77A patent/IT1075298B/it active
- 1977-02-25 CH CH242677A patent/CH634576A5/de not_active IP Right Cessation
- 1977-02-25 DK DK84077A patent/DK84077A/da not_active Application Discontinuation
- 1977-02-25 JP JP2078677A patent/JPS52125195A/ja active Granted
- 1977-02-25 IE IE409/77A patent/IE45651B1/en unknown
- 1977-02-25 DE DE19772708111 patent/DE2708111A1/de not_active Withdrawn
- 1977-02-28 GB GB8392/77A patent/GB1577342A/en not_active Expired
- 1977-02-28 BE BE175338A patent/BE851915A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS613351B2 (enExample) | 1986-01-31 |
| IE45651L (en) | 1977-08-26 |
| DE2708111A1 (de) | 1977-09-01 |
| DK84077A (da) | 1977-08-27 |
| LU76838A1 (enExample) | 1977-09-12 |
| US4029672A (en) | 1977-06-14 |
| JPS52125195A (en) | 1977-10-20 |
| CH634576A5 (de) | 1983-02-15 |
| IE45651B1 (en) | 1982-10-20 |
| BE851915A (fr) | 1977-08-29 |
| IT1075298B (it) | 1985-04-22 |
| NL7701832A (nl) | 1977-08-30 |
| FR2342290A1 (fr) | 1977-09-23 |
| GB1577342A (en) | 1980-10-22 |
| US4107074A (en) | 1978-08-15 |
| FR2342290B1 (enExample) | 1980-02-15 |
| US4107187A (en) | 1978-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |