SU465791A3 - Способ получени 5-арил-(или гетероарил)-3-окси-1н-1,5-бензодиазепин-2,4(3н,5н)-дионов - Google Patents
Способ получени 5-арил-(или гетероарил)-3-окси-1н-1,5-бензодиазепин-2,4(3н,5н)-дионовInfo
- Publication number
- SU465791A3 SU465791A3 SU1740811A SU1740811A SU465791A3 SU 465791 A3 SU465791 A3 SU 465791A3 SU 1740811 A SU1740811 A SU 1740811A SU 1740811 A SU1740811 A SU 1740811A SU 465791 A3 SU465791 A3 SU 465791A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydroxy
- dione
- benzodiazepin
- methyl
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 4
- 125000001072 heteroaryl group Chemical group 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- -1 o-trifluoromethylphenyl Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712103745 DE2103745A1 (de) | 1971-01-27 | 1971-01-27 | Neue 5-AryJ-(bzw. Heteroaryl)-3-hydroxylH-l,5-benzodiazepin-2,4-(3H,5H)-dioneund Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU465791A3 true SU465791A3 (ru) | 1975-03-30 |
Family
ID=5797047
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1740811A SU465791A3 (ru) | 1971-01-27 | 1972-01-24 | Способ получени 5-арил-(или гетероарил)-3-окси-1н-1,5-бензодиазепин-2,4(3н,5н)-дионов |
| SU1926941A SU493971A3 (ru) | 1971-01-27 | 1972-01-24 | Способ получени 5-арил-/или гетероарил/ -3-окси-1н-1,5-бензодиазепин-2,4-/3н,5н/-дионов |
| SU1926940A SU460627A3 (ru) | 1971-01-27 | 1973-01-24 | Способ получени 5-арил-(или гетероарил)-3-окси 1н-1,5-бензодиазепин-2,4-(3н,5н)-дионов |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1926941A SU493971A3 (ru) | 1971-01-27 | 1972-01-24 | Способ получени 5-арил-/или гетероарил/ -3-окси-1н-1,5-бензодиазепин-2,4-/3н,5н/-дионов |
| SU1926940A SU460627A3 (ru) | 1971-01-27 | 1973-01-24 | Способ получени 5-арил-(или гетероарил)-3-окси 1н-1,5-бензодиазепин-2,4-(3н,5н)-дионов |
Country Status (19)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9314981D0 (en) * | 1993-07-20 | 1993-09-01 | Glaxo Spa | Chemical compounds |
-
1971
- 1971-01-27 DE DE19712103745 patent/DE2103745A1/de active Pending
-
1972
- 1972-01-14 RO RO71243A patent/RO60491A/ro unknown
- 1972-01-14 RO RO71244A patent/RO60492A/ro unknown
- 1972-01-14 RO RO69392A patent/RO61669A/ro unknown
- 1972-01-24 SU SU1740811A patent/SU465791A3/ru active
- 1972-01-24 SU SU1926941A patent/SU493971A3/ru active
- 1972-01-25 BG BG021122A patent/BG19176A3/xx unknown
- 1972-01-25 HU HUBO1347A patent/HU164575B/hu unknown
- 1972-01-25 BG BG019569A patent/BG19174A3/xx unknown
- 1972-01-25 BG BG021123A patent/BG21031A3/xx unknown
- 1972-01-25 ES ES399169A patent/ES399169A1/es not_active Expired
- 1972-01-26 AT AT611173A patent/AT315864B/de not_active IP Right Cessation
- 1972-01-26 NL NL7201048A patent/NL7201048A/xx unknown
- 1972-01-26 BE BE778542A patent/BE778542A/xx unknown
- 1972-01-26 GB GB371972A patent/GB1374529A/en not_active Expired
- 1972-01-26 IL IL38643A patent/IL38643A/en unknown
- 1972-01-26 DK DK34672AA patent/DK130411B/da unknown
- 1972-01-26 PL PL1972175545A patent/PL84243B1/pl unknown
- 1972-01-26 AT AT60972A patent/AT315849B/de not_active IP Right Cessation
- 1972-01-26 DD DD160513A patent/DD99376A5/xx unknown
- 1972-01-26 ZA ZA720538A patent/ZA72538B/xx unknown
- 1972-01-26 PL PL1972175546A patent/PL91875B1/pl unknown
- 1972-01-26 AT AT611273A patent/AT316566B/de not_active IP Right Cessation
- 1972-01-26 PL PL1972153120A patent/PL84620B1/pl unknown
- 1972-01-26 AU AU38362/72A patent/AU464682B2/en not_active Expired
- 1972-01-27 IE IE111/72A patent/IE36035B1/xx unknown
- 1972-01-27 FR FR7202739A patent/FR2123474B1/fr not_active Expired
- 1972-01-27 CA CA133,282A patent/CA967957A/en not_active Expired
-
1973
- 1973-01-24 SU SU1926940A patent/SU460627A3/ru active
-
1974
- 1974-04-08 ES ES425108A patent/ES425108A1/es not_active Expired
- 1974-04-08 ES ES425107A patent/ES425107A1/es not_active Expired
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