DE2216837B2 - - Google Patents
Info
- Publication number
- DE2216837B2 DE2216837B2 DE2216837A DE2216837A DE2216837B2 DE 2216837 B2 DE2216837 B2 DE 2216837B2 DE 2216837 A DE2216837 A DE 2216837A DE 2216837 A DE2216837 A DE 2216837A DE 2216837 B2 DE2216837 B2 DE 2216837B2
- Authority
- DE
- Germany
- Prior art keywords
- chloroform
- mixture
- dihydro
- phenyl
- calculated
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 33
- -1 anilino, benzyl Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical group C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical compound C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- OLXBAAZIANHGGR-UHFFFAOYSA-N 1,4,5-benzotriazocine Chemical class N1=CC=NN=CC2=C1C=CC=C2 OLXBAAZIANHGGR-UHFFFAOYSA-N 0.000 claims 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 153
- 239000000203 mixture Substances 0.000 description 99
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 76
- 239000013078 crystal Substances 0.000 description 75
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 68
- 239000000243 solution Substances 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- 238000001953 recrystallisation Methods 0.000 description 35
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
- 229910052938 sodium sulfate Inorganic materials 0.000 description 34
- 235000011152 sodium sulphate Nutrition 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000012141 concentrate Substances 0.000 description 27
- 238000003756 stirring Methods 0.000 description 24
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 241000699670 Mus sp. Species 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 12
- 229960003529 diazepam Drugs 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 9
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 4
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 4
- 229960001076 chlorpromazine Drugs 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 230000004622 sleep time Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000002906 tartaric acid Nutrition 0.000 description 4
- 239000011975 tartaric acid Substances 0.000 description 4
- MJXHGGJZSZSVHT-UHFFFAOYSA-N 4-(2-bromoacetyl)-8-chloro-1-methyl-6-phenyl-3H-1,4,5-benzotriazocin-2-one Chemical compound BrCC(=O)N1CC(N(C2=C(C(=N1)C1=CC=CC=C1)C=C(C=C2)Cl)C)=O MJXHGGJZSZSVHT-UHFFFAOYSA-N 0.000 description 3
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229940075930 picrate Drugs 0.000 description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- HNTDBXYTRPOIMW-UHFFFAOYSA-N 1-methyl-6-phenyl-1,4,5-benzotriazocin-2-one Chemical compound CN1C(C=NN=C(C2=C1C=CC=C2)C2=CC=CC=C2)=O HNTDBXYTRPOIMW-UHFFFAOYSA-N 0.000 description 2
- QFHDDAJVWGTIFD-UHFFFAOYSA-N 4-(2-bromoacetyl)-6-phenyl-1,3-dihydro-1,4,5-benzotriazocin-2-one Chemical compound BrCC(=O)N1CC(NC2=C(C(=N1)C1=CC=CC=C1)C=CC=C2)=O QFHDDAJVWGTIFD-UHFFFAOYSA-N 0.000 description 2
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 229960000212 aminophenazone Drugs 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- MPAVWUYTRNLNPQ-UHFFFAOYSA-N 1-methyl-6-phenyl-3,4-dihydro-1,4,5-benzotriazocin-2-one Chemical compound N=1NCC(=O)N(C)C2=CC=CC=C2C=1C1=CC=CC=C1 MPAVWUYTRNLNPQ-UHFFFAOYSA-N 0.000 description 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- LLPGEPRZHOMDHC-SSZFMOIBSA-N 2-[(z)-c-phenylcarbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(N)C=1C(=N/N)\C1=CC=CC=C1 LLPGEPRZHOMDHC-SSZFMOIBSA-N 0.000 description 1
- WTOFZKZDWDMOBU-UHFFFAOYSA-N 2-bromo-N-[2-[N-[(2-bromoacetyl)amino]-C-phenylcarbonimidoyl]-4-chlorophenyl]acetamide Chemical compound BrCC(=O)NN=C(C1=C(C=CC(=C1)Cl)NC(CBr)=O)C1=CC=CC=C1 WTOFZKZDWDMOBU-UHFFFAOYSA-N 0.000 description 1
- FRASAYRUGNPWBK-UHFFFAOYSA-N 2-bromo-N-[2-[N-[(2-bromoacetyl)amino]-C-phenylcarbonimidoyl]-4-methylphenyl]acetamide Chemical compound BrCC(=O)NN=C(C1=C(C=CC(=C1)C)NC(CBr)=O)C1=CC=CC=C1 FRASAYRUGNPWBK-UHFFFAOYSA-N 0.000 description 1
- GZNHCSWHTBJBRR-UHFFFAOYSA-N 4-(2-bromoacetyl)-1-methyl-6-phenyl-3H-1,4,5-benzotriazocin-2-one Chemical compound BrCC(=O)N1CC(N(C2=C(C(=N1)C1=CC=CC=C1)C=CC=C2)C)=O GZNHCSWHTBJBRR-UHFFFAOYSA-N 0.000 description 1
- PPXZPFDOUYQSLZ-UHFFFAOYSA-N 4-bromo-N-methyl-2-(C-phenylcarbonohydrazonoyl)aniline Chemical group CNC1=C(C(C2=CC=CC=C2)=NN)C=C(C=C1)Br PPXZPFDOUYQSLZ-UHFFFAOYSA-N 0.000 description 1
- WPRRWTZCKYTGRJ-UHFFFAOYSA-N 4-chloro-2-(c-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C(Cl)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 WPRRWTZCKYTGRJ-UHFFFAOYSA-N 0.000 description 1
- DLBGMGBBVLKPNL-UHFFFAOYSA-N 4-fluoro-N-methyl-2-(C-phenylcarbonohydrazonoyl)aniline Chemical compound CNC1=C(C(C2=CC=CC=C2)=NN)C=C(C=C1)F DLBGMGBBVLKPNL-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- WRCYSFWCSNWQLH-UHFFFAOYSA-N 8-chloro-1-methyl-6-phenyl-3,4-dihydro-1,4,5-benzotriazocin-2-one Chemical compound ClC=1C=CC2=C(C(=NNCC(N2C)=O)C2=CC=CC=C2)C1 WRCYSFWCSNWQLH-UHFFFAOYSA-N 0.000 description 1
- KPTCXHGNYUGJAB-UHFFFAOYSA-N 8-chloro-6-phenyl-3,4-dihydro-1H-1,4,5-benzotriazocin-2-one Chemical compound ClC=1C=CC2=C(C(=NNCC(N2)=O)C2=CC=CC=C2)C1 KPTCXHGNYUGJAB-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 1
- YKHYIFFOBCGATI-UHFFFAOYSA-N BrCC(=O)N1CC(N(C2=C(C(=N1)C1=CC=CC=C1)C=C(C=C2)C)C)=O Chemical compound BrCC(=O)N1CC(N(C2=C(C(=N1)C1=CC=CC=C1)C=C(C=C2)C)C)=O YKHYIFFOBCGATI-UHFFFAOYSA-N 0.000 description 1
- ACOCWDATFQOOHP-UHFFFAOYSA-N BrCC(=O)N1CC(NC2=C(C(=N1)C1=CC=CC=C1)C=C(C=C2)C)=O Chemical compound BrCC(=O)N1CC(NC2=C(C(=N1)C1=CC=CC=C1)C=C(C=C2)C)=O ACOCWDATFQOOHP-UHFFFAOYSA-N 0.000 description 1
- YZCWEIDRMSDYOO-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NN=CC(NC2=C1C=CC=C2)=O Chemical compound C1(=CC=CC=C1)C1=NN=CC(NC2=C1C=CC=C2)=O YZCWEIDRMSDYOO-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
- 229910020314 ClBr Inorganic materials 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- HCYJIOAYTWGXBL-UHFFFAOYSA-N N-methyl-2-(C-phenylcarbonohydrazonoyl)aniline Chemical compound CNC1=C(C(C2=CC=CC=C2)=NN)C=CC=C1 HCYJIOAYTWGXBL-UHFFFAOYSA-N 0.000 description 1
- LSBQGDGELAJQMB-UHFFFAOYSA-N O=C(CBr)N(C1)N=C(C2=CC=CC=C2)C(C=C(C=C2)Br)=C2NC1=O Chemical compound O=C(CBr)N(C1)N=C(C2=CC=CC=C2)C(C=C(C=C2)Br)=C2NC1=O LSBQGDGELAJQMB-UHFFFAOYSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 206010039740 Screaming Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AGKPGIOZNCJFTQ-UHFFFAOYSA-N [2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=CC=C1C(=O)C1=CC=CC=C1 AGKPGIOZNCJFTQ-UHFFFAOYSA-N 0.000 description 1
- DZFVLVSXNCYTGE-UHFFFAOYSA-N [5-bromo-2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 DZFVLVSXNCYTGE-UHFFFAOYSA-N 0.000 description 1
- UTJFPYHINXBLFT-UHFFFAOYSA-N [5-methyl-2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=C(C)C=C1C(=O)C1=CC=CC=C1 UTJFPYHINXBLFT-UHFFFAOYSA-N 0.000 description 1
- YKSNHLNTLVRITE-UHFFFAOYSA-N [Br].CC(Br)=O Chemical compound [Br].CC(Br)=O YKSNHLNTLVRITE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ASGJEMPQQVNTGO-UHFFFAOYSA-N benzene chloroform Chemical compound C(Cl)(Cl)Cl.C1=CC=CC=C1.C1=CC=CC=C1 ASGJEMPQQVNTGO-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910001853 inorganic hydroxide Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 1
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical group O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000004623 sleep-prolonging effect Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SQMCFUSVGSBKFK-UHFFFAOYSA-M sodium;5-(cyclohexen-1-yl)-1,5-dimethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)[N-]C(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-M 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2142171A JPS549199B1 (enrdf_load_stackoverflow) | 1971-04-08 | 1971-04-08 | |
| JP2142271A JPS565745B1 (enrdf_load_stackoverflow) | 1971-04-08 | 1971-04-08 | |
| JP2142871A JPS561314B1 (enrdf_load_stackoverflow) | 1971-04-08 | 1971-04-08 | |
| JP2142371A JPS56433B1 (enrdf_load_stackoverflow) | 1971-04-08 | 1971-04-08 | |
| JP2855872A JPS563350B2 (enrdf_load_stackoverflow) | 1971-04-08 | 1972-03-23 | |
| JP2855672A JPS5521739B2 (enrdf_load_stackoverflow) | 1971-04-08 | 1972-03-23 | |
| JP2855772A JPS563349B2 (enrdf_load_stackoverflow) | 1971-04-08 | 1972-03-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2216837A1 DE2216837A1 (de) | 1972-10-26 |
| DE2216837B2 true DE2216837B2 (enrdf_load_stackoverflow) | 1974-12-12 |
| DE2216837C3 DE2216837C3 (de) | 1975-07-31 |
Family
ID=27563938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2216837A Expired DE2216837C3 (de) | 1971-04-08 | 1972-04-07 | 1,4,5-Benzotrlazocinderivate, ihre Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate |
Country Status (7)
| Country | Link |
|---|---|
| JP (3) | JPS563350B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1029723A (enrdf_load_stackoverflow) |
| CH (1) | CH592631A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2216837C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2132773B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1380297A (enrdf_load_stackoverflow) |
| NL (1) | NL148238B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57202790U (enrdf_load_stackoverflow) * | 1981-06-19 | 1982-12-23 | ||
| KR101753917B1 (ko) | 2009-03-02 | 2017-07-04 | 옥스포드 어드밴스드 서패이시즈 리미티드 | 공유결합 3차원 네트워크를 형성할 수 있는 화학제 |
| CN106946808A (zh) * | 2017-04-10 | 2017-07-14 | 苏州大学 | 苯并[1,3,5]三唑辛酮衍生物的合成方法 |
| CN114931976A (zh) * | 2019-12-25 | 2022-08-23 | 合肥工业大学 | 一种氮乙酰氨基二苯甲酮腙的用途 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL27232A (en) * | 1966-01-24 | 1971-06-23 | Sparamedica Ag | Process for the manufacture of 3-hydroxy-1,4-benzodiazepin-2-one and intermediates thereof |
-
1972
- 1972-03-23 JP JP2855872A patent/JPS563350B2/ja not_active Expired
- 1972-03-23 JP JP2855672A patent/JPS5521739B2/ja not_active Expired
- 1972-03-23 JP JP2855772A patent/JPS563349B2/ja not_active Expired
- 1972-04-06 GB GB1600372A patent/GB1380297A/en not_active Expired
- 1972-04-07 CH CH516572A patent/CH592631A5/xx not_active IP Right Cessation
- 1972-04-07 NL NL727204673A patent/NL148238B/xx not_active IP Right Cessation
- 1972-04-07 FR FR7212317A patent/FR2132773B1/fr not_active Expired
- 1972-04-07 CA CA139,256A patent/CA1029723A/en not_active Expired
- 1972-04-07 DE DE2216837A patent/DE2216837C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4897886A (enrdf_load_stackoverflow) | 1973-12-13 |
| JPS4897856A (enrdf_load_stackoverflow) | 1973-12-13 |
| GB1380297A (en) | 1975-01-15 |
| CA1029723A (en) | 1978-04-18 |
| JPS5521739B2 (enrdf_load_stackoverflow) | 1980-06-12 |
| NL7204673A (enrdf_load_stackoverflow) | 1972-10-10 |
| NL148238B (nl) | 1976-01-15 |
| JPS563349B2 (enrdf_load_stackoverflow) | 1981-01-24 |
| CH592631A5 (enrdf_load_stackoverflow) | 1977-10-31 |
| FR2132773B1 (enrdf_load_stackoverflow) | 1976-04-16 |
| JPS4897887A (enrdf_load_stackoverflow) | 1973-12-13 |
| FR2132773A1 (enrdf_load_stackoverflow) | 1972-11-24 |
| JPS563350B2 (enrdf_load_stackoverflow) | 1981-01-24 |
| DE2216837C3 (de) | 1975-07-31 |
| DE2216837A1 (de) | 1972-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |