SU506293A3 - Способ получени алкил-5-амино-10-дигидро-10,11-дибензо-( )-азепинов - Google Patents
Способ получени алкил-5-амино-10-дигидро-10,11-дибензо-( )-азепиновInfo
- Publication number
- SU506293A3 SU506293A3 SU1955897A SU1955897A SU506293A3 SU 506293 A3 SU506293 A3 SU 506293A3 SU 1955897 A SU1955897 A SU 1955897A SU 1955897 A SU1955897 A SU 1955897A SU 506293 A3 SU506293 A3 SU 506293A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- azepines
- dibenzo
- dihydro
- amino
- amide
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- -1 naphthyl lithium Chemical compound 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- 241001425930 Latina Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7232287A FR2198942B1 (US20030204162A1-20031030-M00001.png) | 1972-09-12 | 1972-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU506293A3 true SU506293A3 (ru) | 1976-03-05 |
Family
ID=9104159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1955897A SU506293A3 (ru) | 1972-09-12 | 1973-09-11 | Способ получени алкил-5-амино-10-дигидро-10,11-дибензо-( )-азепинов |
Country Status (19)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5561127A (en) * | 1994-12-19 | 1996-10-01 | Allelix Biopharmaceuticals, Inc. | Muscarinic receptor ligands |
| US7317030B2 (en) | 2004-02-26 | 2008-01-08 | 4Sc Ag | Compounds as inhibitors of cell proliferation and viral infections |
| EP1568696A1 (en) * | 2004-02-26 | 2005-08-31 | 4Sc Ag | Compounds as inhibitors of cell proliferation and viral infections |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1532301A (fr) * | 1967-01-18 | 1968-07-12 | Rhone Poulenc Sa | Nouveaux dérivés de la dibenzazépine et leur préparation |
| BE754532A (fr) * | 1969-08-07 | 1971-02-08 | Rhone Poulenc Sa | Nouveaux derives de la dibenzazepine et leur preparation |
| FR2092877A1 (en) * | 1970-06-26 | 1972-01-28 | Rhone Poulenc Sa | Chloro 10 (or 11) amino 10,11 dihydro dibenzazepine derivs - with cns activity |
| FR2122305B1 (US20030204162A1-20031030-M00001.png) * | 1971-01-19 | 1973-11-30 | Rhone Poulenc Sa |
-
1972
- 1972-09-12 FR FR7232287A patent/FR2198942B1/fr not_active Expired
-
1973
- 1973-09-04 NL NL7312212A patent/NL7312212A/xx not_active Application Discontinuation
- 1973-09-10 HU HURO747A patent/HU166484B/hu unknown
- 1973-09-10 DD DD173382A patent/DD109218A5/xx unknown
- 1973-09-11 GB GB4272973A patent/GB1384486A/en not_active Expired
- 1973-09-11 BR BR7024/73A patent/BR7307024D0/pt unknown
- 1973-09-11 CH CH1297173A patent/CH574931A5/xx not_active IP Right Cessation
- 1973-09-11 BE BE135559A patent/BE804736A/xx unknown
- 1973-09-11 US US05/396,143 patent/US4024127A/en not_active Expired - Lifetime
- 1973-09-11 DK DK499773AA patent/DK136362B/da unknown
- 1973-09-11 SU SU1955897A patent/SU506293A3/ru active
- 1973-09-11 JP JP48101730A patent/JPS49100095A/ja active Pending
- 1973-09-11 AR AR250028A patent/AR196685A1/es active
- 1973-09-11 SE SE7312377A patent/SE399886B/xx unknown
- 1973-09-11 LU LU68401A patent/LU68401A1/xx unknown
- 1973-09-12 AT AT789873A patent/AT333769B/de not_active IP Right Cessation
- 1973-09-12 DE DE19732345972 patent/DE2345972A1/de active Pending
- 1973-09-12 IT IT28850/73A patent/IT1006605B/it active
- 1973-09-12 ES ES418708A patent/ES418708A1/es not_active Expired
-
1975
- 1975-10-17 SE SE7511681A patent/SE403474B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2198942A1 (US20030204162A1-20031030-M00001.png) | 1974-04-05 |
| BR7307024D0 (pt) | 1974-07-18 |
| DD109218A5 (US20030204162A1-20031030-M00001.png) | 1974-10-20 |
| SE7511681L (sv) | 1975-10-17 |
| CH574931A5 (US20030204162A1-20031030-M00001.png) | 1976-04-30 |
| AR196685A1 (es) | 1974-02-12 |
| GB1384486A (en) | 1975-02-19 |
| ATA789873A (de) | 1976-04-15 |
| HU166484B (US20030204162A1-20031030-M00001.png) | 1975-03-28 |
| FR2198942B1 (US20030204162A1-20031030-M00001.png) | 1975-03-14 |
| LU68401A1 (US20030204162A1-20031030-M00001.png) | 1974-03-14 |
| AT333769B (de) | 1976-12-10 |
| ES418708A1 (es) | 1976-02-16 |
| JPS49100095A (US20030204162A1-20031030-M00001.png) | 1974-09-20 |
| BE804736A (fr) | 1974-03-11 |
| IT1006605B (it) | 1976-10-20 |
| DK136362B (da) | 1977-10-03 |
| SE399886B (sv) | 1978-03-06 |
| US4024127A (en) | 1977-05-17 |
| SE403474B (sv) | 1978-08-21 |
| DE2345972A1 (de) | 1974-03-21 |
| DK136362C (US20030204162A1-20031030-M00001.png) | 1978-02-27 |
| NL7312212A (US20030204162A1-20031030-M00001.png) | 1974-03-14 |
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