PL57248B1 - - Google Patents
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- PL57248B1 PL57248B1 PL116548A PL11654866A PL57248B1 PL 57248 B1 PL57248 B1 PL 57248B1 PL 116548 A PL116548 A PL 116548A PL 11654866 A PL11654866 A PL 11654866A PL 57248 B1 PL57248 B1 PL 57248B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- hydrolyzed
- lower alkyl
- compound
- solution
- Prior art date
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 34
- -1 nitro, amino Chemical group 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 230000002152 alkylating effect Effects 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical compound [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 150000001557 benzodiazepines Chemical class 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000203 mixture Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 239000011976 maleic acid Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000012670 alkaline solution Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 125000006308 propyl amino group Chemical group 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002027 dichloromethane extract Substances 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RWWODOMYDKTRCF-UHFFFAOYSA-N [2-[3-(dimethylamino)propylamino]-5-nitrophenyl]-phenylmethanone Chemical compound CN(CCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-])C RWWODOMYDKTRCF-UHFFFAOYSA-N 0.000 description 2
- VVUUZVWYATYYGT-UHFFFAOYSA-N [2-[3-(dimethylamino)propylamino]-5-nitrophenyl]-phenylmethanone hydrochloride Chemical compound Cl.CN(CCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-])C VVUUZVWYATYYGT-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- YVHPHQBRUPLYOS-UHFFFAOYSA-N dichloromethane;methane Chemical compound C.ClCCl YVHPHQBRUPLYOS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 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
- RIUVIMLHUDDDHK-UHFFFAOYSA-N 7-chloro-1-(3-chloropropyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCCl)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 RIUVIMLHUDDDHK-UHFFFAOYSA-N 0.000 description 1
- HCGXHCQLJCFGAB-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(3-piperazin-1-ylpropyl)-3h-1,4-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C(C1=CC(Cl)=CC=C11)=NCC(=O)N1CCCN1CCNCC1 HCGXHCQLJCFGAB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- PDTMUIPFJUJPKI-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.BrC=1C=CC(=C(C(=O)C2=CC=CC=C2)C1)NCCCN(C)C Chemical compound C(C=C/C(=O)O)(=O)O.BrC=1C=CC(=C(C(=O)C2=CC=CC=C2)C1)NCCCN(C)C PDTMUIPFJUJPKI-UHFFFAOYSA-N 0.000 description 1
- KYIZDYWFIJNVJV-UHFFFAOYSA-N CCNCCNC1=C(C=C(Cl)C=C1)C(=O)C1=CC=CC=C1 Chemical compound CCNCCNC1=C(C=C(Cl)C=C1)C(=O)C1=CC=CC=C1 KYIZDYWFIJNVJV-UHFFFAOYSA-N 0.000 description 1
- PNKQGJKDUGDZKX-UHFFFAOYSA-N Cl.ClC=1C=CC(=C(C(=O)C2=CC=CC=C2)C1)NCCCNC Chemical compound Cl.ClC=1C=CC(=C(C(=O)C2=CC=CC=C2)C1)NCCCNC PNKQGJKDUGDZKX-UHFFFAOYSA-N 0.000 description 1
- PSPZRKYTCZLWGN-UHFFFAOYSA-N Cl.NCCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)Cl Chemical compound Cl.NCCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)Cl PSPZRKYTCZLWGN-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 101100166829 Mus musculus Cenpk gene Proteins 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- HNKXCJXKXCSLAK-UHFFFAOYSA-N [2-(3-aminopropylamino)-5-nitrophenyl]-phenylmethanone Chemical compound NCCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-] HNKXCJXKXCSLAK-UHFFFAOYSA-N 0.000 description 1
- BVLQQZBPPMLLAY-UHFFFAOYSA-N [5-chloro-2-(3-chloropropylamino)phenyl]-phenylmethanone Chemical compound ClCCCNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 BVLQQZBPPMLLAY-UHFFFAOYSA-N 0.000 description 1
- WJGYSTDNMLNZNH-UHFFFAOYSA-N [5-chloro-2-[3-(dimethylamino)propylamino]phenyl]-(2-fluorophenyl)methanone Chemical compound CN(C)CCCNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F WJGYSTDNMLNZNH-UHFFFAOYSA-N 0.000 description 1
- WNLLCLUIZQVOTO-UHFFFAOYSA-N [5-chloro-2-[3-(dimethylamino)propylamino]phenyl]-phenylmethanone Chemical compound CN(C)CCCNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WNLLCLUIZQVOTO-UHFFFAOYSA-N 0.000 description 1
- ZKESTXHTKQWPHZ-UHFFFAOYSA-N [5-chloro-2-[3-(dimethylamino)propylamino]phenyl]-phenylmethanone hydrochloride Chemical compound Cl.ClC=1C=CC(=C(C(=O)C2=CC=CC=C2)C1)NCCCN(C)C ZKESTXHTKQWPHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- JERMANHOFDIPQQ-UHFFFAOYSA-N dimethyl-[3-(7-nitro-2-oxo-5-phenyl-3h-1,4-benzodiazepin-1-yl)propyl]azanium;chloride Chemical compound [Cl-].N=1CC(=O)N(CCC[NH+](C)C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 JERMANHOFDIPQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL57248B1 true PL57248B1 (cs) | 1969-02-26 |
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