SU464112A3 - Способ получени производных дигидро10,11-дибезо-( )-азепина - Google Patents
Способ получени производных дигидро10,11-дибезо-( )-азепинаInfo
- Publication number
- SU464112A3 SU464112A3 SU1313323A SU1313323A SU464112A3 SU 464112 A3 SU464112 A3 SU 464112A3 SU 1313323 A SU1313323 A SU 1313323A SU 1313323 A SU1313323 A SU 1313323A SU 464112 A3 SU464112 A3 SU 464112A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ether
- azepine
- sodium
- dibezo
- total amount
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- -1 phen-ylalkyl radical Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 229910001023 sodium amalgam Inorganic materials 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- PRHCBRXAHBBRKA-UHFFFAOYSA-N 2-(2-hydroxypropan-2-yloxy)propan-2-ol Chemical compound CC(C)(O)OC(C)(C)O PRHCBRXAHBBRKA-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 230000002378 acidificating effect Effects 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
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Combustion Methods Of Internal-Combustion Engines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Securing Globes, Refractors, Reflectors Or The Like (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR91646A FR1532301A (fr) | 1967-01-18 | 1967-01-18 | Nouveaux dérivés de la dibenzazépine et leur préparation |
| FR127611A FR94320E (fr) | 1967-01-18 | 1967-11-09 | Nouveaux dérives de la dibenzazépine et leur préparation. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU464112A3 true SU464112A3 (ru) | 1975-03-15 |
Family
ID=26174548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1313323A SU464112A3 (ru) | 1967-01-18 | 1968-01-18 | Способ получени производных дигидро10,11-дибезо-( )-азепина |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3622565A (enExample) |
| AT (6) | AT279630B (enExample) |
| BE (1) | BE709523A (enExample) |
| CH (1) | CH482677A (enExample) |
| DE (1) | DE1695666C3 (enExample) |
| DK (2) | DK120950B (enExample) |
| ES (5) | ES349459A1 (enExample) |
| FI (1) | FI48927C (enExample) |
| FR (2) | FR1532301A (enExample) |
| GB (2) | GB1180165A (enExample) |
| IE (1) | IE31926B1 (enExample) |
| IL (1) | IL29340A (enExample) |
| LU (1) | LU55297A1 (enExample) |
| NL (1) | NL156137B (enExample) |
| NO (2) | NO125677B (enExample) |
| OA (1) | OA03401A (enExample) |
| SE (2) | SE338995B (enExample) |
| SU (1) | SU464112A3 (enExample) |
| YU (2) | YU32142B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3882235A (en) * | 1969-06-24 | 1975-05-06 | Rhone Poulenc Sa | Fungicidal compositions comprising A 10, 11 dihydrodibenzo {8 b,f{9 {0 azepine derivative |
| FR2198942B1 (enExample) * | 1972-09-12 | 1975-03-14 | Rhone Poulenc Ind | |
| FI75561C (fi) * | 1979-10-30 | 1988-07-11 | Ciba Geigy Ag | Foerfarande foer framstaellning av 5- karbamoyl-10-oxo-10,11-dihydro-5h-dibens/b,f/azepin och daertill noedvaendiga mellanprodukter. |
| US20070225217A1 (en) | 2005-11-09 | 2007-09-27 | Combinatorx, Incorporated | Methods, compositions, and kits for the treatment of medical conditions |
| KR101539797B1 (ko) | 2007-11-28 | 2015-07-27 | 넥타르 테라퓨틱스 | 올리고머-삼환계 콘쥬게이트 |
| WO2011091050A1 (en) | 2010-01-19 | 2011-07-28 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
| JP6002144B2 (ja) | 2010-12-10 | 2016-10-05 | ネクター セラピューティクス | ヒドロキシル化三環化合物 |
| KR102824220B1 (ko) | 2018-09-28 | 2025-06-23 | 그리피스 유니버시티 | 병원체 활성 조절을 위한 제제 및 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH457447A (de) * | 1965-07-26 | 1968-06-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Azepinderivaten |
-
1967
- 1967-01-18 FR FR91646A patent/FR1532301A/fr not_active Expired
- 1967-11-09 FR FR127611A patent/FR94320E/fr not_active Expired
-
1968
- 1968-01-09 OA OA53156A patent/OA03401A/xx unknown
- 1968-01-10 NL NL6800363.A patent/NL156137B/xx not_active IP Right Cessation
- 1968-01-16 SE SE00553/68A patent/SE338995B/xx unknown
- 1968-01-16 FI FI680114A patent/FI48927C/fi active
- 1968-01-16 SE SE04482/70A patent/SE350971B/xx unknown
- 1968-01-16 DK DK15068AA patent/DK120950B/da not_active IP Right Cessation
- 1968-01-17 US US698436A patent/US3622565A/en not_active Expired - Lifetime
- 1968-01-17 IE IE57/68A patent/IE31926B1/xx unknown
- 1968-01-17 NO NO0200/68A patent/NO125677B/no unknown
- 1968-01-17 BE BE709523A patent/BE709523A/fr unknown
- 1968-01-17 IL IL29340A patent/IL29340A/en unknown
- 1968-01-17 LU LU55297D patent/LU55297A1/xx unknown
- 1968-01-18 AT AT03859/69A patent/AT279630B/de not_active IP Right Cessation
- 1968-01-18 SU SU1313323A patent/SU464112A3/ru active
- 1968-01-18 AT AT386169A patent/AT279632B/de not_active IP Right Cessation
- 1968-01-18 GB GB23183/69A patent/GB1180165A/en not_active Expired
- 1968-01-18 CH CH76368A patent/CH482677A/fr not_active IP Right Cessation
- 1968-01-18 AT AT53668A patent/AT279619B/de not_active IP Right Cessation
- 1968-01-18 AT AT03858/69A patent/AT281842B/de not_active IP Right Cessation
- 1968-01-18 ES ES349459A patent/ES349459A1/es not_active Expired
- 1968-01-18 DE DE1695666A patent/DE1695666C3/de not_active Expired
- 1968-01-18 AT AT385769A patent/AT279629B/de not_active IP Right Cessation
- 1968-01-18 GB GB2858/68A patent/GB1180164A/en not_active Expired
- 1968-01-18 AT AT03860/69A patent/AT279631B/de not_active IP Right Cessation
- 1968-01-18 YU YU0121/68A patent/YU32142B/xx unknown
- 1968-05-30 ES ES354502A patent/ES354502A1/es not_active Expired
- 1968-05-30 ES ES354500A patent/ES354500A1/es not_active Expired
- 1968-05-30 ES ES354501A patent/ES354501A1/es not_active Expired
- 1968-05-30 ES ES354499A patent/ES354499A1/es not_active Expired
-
1969
- 1969-01-14 DK DK19669AA patent/DK118135B/da not_active IP Right Cessation
-
1971
- 1971-11-05 NO NO4096/71*[A patent/NO126527B/no unknown
-
1972
- 1972-10-30 YU YU2692/72A patent/YU33110B/xx unknown
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