SU309516A1 - - Google Patents
Info
- Publication number
- SU309516A1 SU309516A1 SU1272981A SU1272981A SU309516A1 SU 309516 A1 SU309516 A1 SU 309516A1 SU 1272981 A SU1272981 A SU 1272981A SU 1272981 A SU1272981 A SU 1272981A SU 309516 A1 SU309516 A1 SU 309516A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dihydro
- benzodiazepin
- chloro
- fluorophenyl
- chlorophenyl
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 6
- -1 for example Substances 0.000 description 6
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atoms Chemical group C* 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- 229940053197 Benzodiazepine derivative antiepileptics Drugs 0.000 description 3
- 229940054023 Benzodiazepine derivative anxiolytics Drugs 0.000 description 3
- 229940053995 Benzodiazepine derivative hypnotics and sedatives Drugs 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001557 benzodiazepines Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RNAODKZCUVVPEN-UHFFFAOYSA-N 1H-indol-2-ylmethanamine Chemical class C1=CC=C2NC(CN)=CC2=C1 RNAODKZCUVVPEN-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1H-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- RNBOUZKGTVHUEX-UHFFFAOYSA-N 5-(2-bromophenyl)-7-chloro-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1Br RNBOUZKGTVHUEX-UHFFFAOYSA-N 0.000 description 1
- DXAIBZTWPCDCFJ-UHFFFAOYSA-N 5-(2-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound ClC1=CC=CC=C1C1=NCC(=O)NC2=CC=CC=C12 DXAIBZTWPCDCFJ-UHFFFAOYSA-N 0.000 description 1
- ZFYAQIQNROJRTO-UHFFFAOYSA-N 5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=CC=CC=C12 ZFYAQIQNROJRTO-UHFFFAOYSA-N 0.000 description 1
- KMADJPBGARDOAO-UHFFFAOYSA-N 7-bromo-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1F KMADJPBGARDOAO-UHFFFAOYSA-N 0.000 description 1
- LTLABSJDFXKDGO-UHFFFAOYSA-N C1(CC1)CN1C(CN=C(C2=C1C=CC(=C2)Br)C2=C(C=CC=C2)F)=O Chemical compound C1(CC1)CN1C(CN=C(C2=C1C=CC(=C2)Br)C2=C(C=CC=C2)F)=O LTLABSJDFXKDGO-UHFFFAOYSA-N 0.000 description 1
- JTRYMVKIODXAPJ-UHFFFAOYSA-N C1(CCCC1)CN1C(CN=C(C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)F)=O Chemical compound C1(CCCC1)CN1C(CN=C(C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)F)=O JTRYMVKIODXAPJ-UHFFFAOYSA-N 0.000 description 1
- KAVLPKMKWXGSKW-UHFFFAOYSA-N Cl.C1(CC1)CN1C(=C(C2=CC(=CC=C12)Cl)C1=C(C=CC=C1)F)N Chemical compound Cl.C1(CC1)CN1C(=C(C2=CC(=CC=C12)Cl)C1=C(C=CC=C1)F)N KAVLPKMKWXGSKW-UHFFFAOYSA-N 0.000 description 1
- IETPUSPHTZJHFW-UHFFFAOYSA-N Cl.CN1C(=C(C2=CC(=CC=C12)Cl)C1=C(C=CC=C1)F)CN Chemical compound Cl.CN1C(=C(C2=CC(=CC=C12)Cl)C1=C(C=CC=C1)F)CN IETPUSPHTZJHFW-UHFFFAOYSA-N 0.000 description 1
- HRJRNGDMFSXYAI-UHFFFAOYSA-N Cl.ClC=1C=CC2=C(C(=NCC(N2)=O)C2=C(C=CC=C2)F)C1 Chemical compound Cl.ClC=1C=CC2=C(C(=NCC(N2)=O)C2=C(C=CC=C2)F)C1 HRJRNGDMFSXYAI-UHFFFAOYSA-N 0.000 description 1
- CHIFCDOIPRCHCF-UHFFFAOYSA-N Delorazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl CHIFCDOIPRCHCF-UHFFFAOYSA-N 0.000 description 1
- VPAYQWRBBOGGPY-UHFFFAOYSA-N Diclazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl VPAYQWRBBOGGPY-UHFFFAOYSA-N 0.000 description 1
- ROYOYTLGDLIGBX-UHFFFAOYSA-N Fludiazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F ROYOYTLGDLIGBX-UHFFFAOYSA-N 0.000 description 1
- QCBMAMBBAZMMGQ-UHFFFAOYSA-N NCC=1NC2=CC=C(C=C2C1C1=C(C=CC=C1)Cl)Cl Chemical compound NCC=1NC2=CC=C(C=C2C1C1=C(C=CC=C1)Cl)Cl QCBMAMBBAZMMGQ-UHFFFAOYSA-N 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000005020 pharmaceutical industry Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU309516A1 true SU309516A1 (US06534493-20030318-C00166.png) |
Family
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