SU563916A3 - Способ получени производных 1,4-бензодиазепина - Google Patents
Способ получени производных 1,4-бензодиазепинаInfo
- Publication number
- SU563916A3 SU563916A3 SU7402067357A SU2067357A SU563916A3 SU 563916 A3 SU563916 A3 SU 563916A3 SU 7402067357 A SU7402067357 A SU 7402067357A SU 2067357 A SU2067357 A SU 2067357A SU 563916 A3 SU563916 A3 SU 563916A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- general formula
- hydrogen
- chlorophenyl
- dihydro
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 title claims description 5
- -1 piperidino- Chemical class 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 159000000000 sodium salts Chemical class 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
- 239000005695 Ammonium acetate Substances 0.000 description 5
- 235000019257 ammonium acetate Nutrition 0.000 description 5
- 229940043376 ammonium acetate Drugs 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KJVSWSJNSWIZDX-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-(hydroxymethylidene)-1-methyl-1,4-benzodiazepin-2-one Chemical compound CN1C2=CC=C(Cl)C=C2C(=NC(=CO)C1=O)C1=C(Cl)C=CC=C1 KJVSWSJNSWIZDX-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 1
- RIUPGPYCWKJQKQ-UHFFFAOYSA-N 3-(aminomethylidene)-7-bromo-5-(2-chlorophenyl)-1-methyl-1,4-benzodiazepin-2-one Chemical compound N=1C(=CN)C(=O)N(C)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1Cl RIUPGPYCWKJQKQ-UHFFFAOYSA-N 0.000 description 1
- MRCIFUDUMNRJEC-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(hydroxymethylidene)-7-iodo-1-methyl-1,4-benzodiazepin-2-one Chemical compound ClC1=C(C=CC=C1)C1=NC(C(N(C2=C1C=C(C=C2)I)C)=O)=CO MRCIFUDUMNRJEC-UHFFFAOYSA-N 0.000 description 1
- VUEJOVVKJIURJW-UHFFFAOYSA-N 7-bromo-5-(2-chlorophenyl)-1-methyl-3-(morpholin-4-ylmethylidene)-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Br)C=C2C(C=2C(=CC=CC=2)Cl)=NC1=CN1CCOCC1 VUEJOVVKJIURJW-UHFFFAOYSA-N 0.000 description 1
- YRHGJNLBSNSMHU-UHFFFAOYSA-N 7-bromo-5-(2-chlorophenyl)-3-(ethylaminomethylidene)-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2N(C)C(=O)C(=CNCC)N=C1C1=CC=CC=C1Cl YRHGJNLBSNSMHU-UHFFFAOYSA-N 0.000 description 1
- AAAYQZTZQYGHQF-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-(dimethylaminomethylidene)-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)C(=CN(C)C)N=C1C1=CC=CC=C1Cl AAAYQZTZQYGHQF-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- YZSMYWMTCGQSEC-UHFFFAOYSA-N azane methyl acetate Chemical compound C(C)(=O)OC.N YZSMYWMTCGQSEC-UHFFFAOYSA-N 0.000 description 1
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NCHPDGCQTUJYKK-UHFFFAOYSA-N pyrrolidin-1-ium;acetate Chemical compound CC(O)=O.C1CCNC1 NCHPDGCQTUJYKK-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732326657 DE2326657A1 (de) | 1973-05-25 | 1973-05-25 | Neue verfahren zur herstellung von 1,4-benzodiazepinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU563916A3 true SU563916A3 (ru) | 1977-06-30 |
Family
ID=5882116
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402065459A SU572203A3 (ru) | 1973-05-25 | 1974-10-09 | Способ получени 1,4-бензодиазепинов |
| SU7402067357A SU563916A3 (ru) | 1973-05-25 | 1974-10-09 | Способ получени производных 1,4-бензодиазепина |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402065459A SU572203A3 (ru) | 1973-05-25 | 1974-10-09 | Способ получени 1,4-бензодиазепинов |
Country Status (8)
-
1973
- 1973-05-25 DE DE19732326657 patent/DE2326657A1/de active Pending
- 1973-07-09 CH CH1371076A patent/CH590855A5/xx not_active IP Right Cessation
- 1973-07-09 CH CH1370976A patent/CH589633A5/xx not_active IP Right Cessation
- 1973-07-10 BG BG2533673A patent/BG21407A3/xx unknown
- 1973-07-10 BG BG026530A patent/BG21219A3/xx unknown
- 1973-07-11 PL PL17820873A patent/PL92133B1/pl unknown
- 1973-07-11 AT AT1008374A patent/AT327925B/de not_active IP Right Cessation
- 1973-07-11 AT AT1008473A patent/ATA1008474A/de unknown
- 1973-07-11 PL PL17820973A patent/PL92134B1/pl unknown
- 1973-07-11 AT AT1008474A patent/AT327926B/de not_active IP Right Cessation
- 1973-07-12 CS CS3273A patent/CS176250B2/cs unknown
-
1974
- 1974-01-16 ES ES422320A patent/ES422320A1/es not_active Expired
- 1974-01-16 ES ES422321A patent/ES422321A1/es not_active Expired
- 1974-10-09 SU SU7402065459A patent/SU572203A3/ru active
- 1974-10-09 SU SU7402067357A patent/SU563916A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2326657A1 (de) | 1974-12-12 |
| SU572203A3 (ru) | 1977-09-05 |
| AT327925B (de) | 1976-02-25 |
| CH589633A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-15 |
| ES422321A1 (es) | 1976-04-16 |
| BG21219A3 (bg) | 1976-03-20 |
| ES422320A1 (es) | 1976-04-16 |
| CS176250B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-06-30 |
| ATA1008374A (de) | 1975-05-15 |
| PL92134B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-03-31 |
| AT327926B (de) | 1976-02-25 |
| CH590855A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-31 |
| ATA1008474A (de) | 1975-05-15 |
| BG21407A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-20 |
| PL92133B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-03-31 |
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