DE1468283C - - Google Patents
Info
- Publication number
- DE1468283C DE1468283C DE19631468283 DE1468283A DE1468283C DE 1468283 C DE1468283 C DE 1468283C DE 19631468283 DE19631468283 DE 19631468283 DE 1468283 A DE1468283 A DE 1468283A DE 1468283 C DE1468283 C DE 1468283C
- Authority
- DE
- Germany
- Prior art keywords
- dibenzo
- dimethylsulfamoyl
- isomer
- benzene
- dimethylaminopropylidene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical class C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002588 toxic Effects 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- -1 3-dimethylsulfamoyl-5- (3-dimethylaminopropylidene) - 5 H - dibenzo [a, d] cycloheptene hydrogen oxalate Chemical compound 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 230000003000 nontoxic Effects 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KMRMBJFKDZYLAN-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]-N,N-dimethyldibenzo[1,3-e:1',2'-f][7]annulene-2-sulfonamide Chemical compound C1=CC2=CC=C(S(=O)(=O)N(C)C)C=C2C(=CCCN(C)C)C2=CC=CC=C21 KMRMBJFKDZYLAN-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- 102100000129 CHURC1 Human genes 0.000 description 2
- 101710014631 CHURC1 Proteins 0.000 description 2
- OEWBBZXCPSULTG-UHFFFAOYSA-N ClC1=CC2=C(C=CC3=C(C2=CCCN(C)C)C=C(C=C3)S(N(C)C)(=O)=O)C=C1 Chemical class ClC1=CC2=C(C=CC3=C(C2=CCCN(C)C)C=C(C=C3)S(N(C)C)(=O)=O)C=C1 OEWBBZXCPSULTG-UHFFFAOYSA-N 0.000 description 2
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N Cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N Trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000001257 hydrogen Chemical group 0.000 description 2
- 229910052739 hydrogen Chemical group 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229940075930 picrate Drugs 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002936 tranquilizing Effects 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- IXNZARLZBMCANF-UHFFFAOYSA-N 2-chloro-5,6-dihydrodibenzo[3,1-[7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC(Cl)=CC=C21 IXNZARLZBMCANF-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- OXMNPBBADIOGAZ-UHFFFAOYSA-N CN(S(=O)(=O)C=1C=CC2=C(C(C3=C(C=C2)C=CC=C3)(O)CCCN(C)C)C1)C Chemical compound CN(S(=O)(=O)C=1C=CC2=C(C(C3=C(C=C2)C=CC=C3)(O)CCCN(C)C)C1)C OXMNPBBADIOGAZ-UHFFFAOYSA-N 0.000 description 1
- JHNTXVXZXZPYQQ-UHFFFAOYSA-N ClC1=CC2=C(C=CC3=C(C2(O)CCCN(C)C)C=C(C=C3)S(N(C)C)(=O)=O)C=C1 Chemical compound ClC1=CC2=C(C=CC3=C(C2(O)CCCN(C)C)C=C(C=C3)S(N(C)C)(=O)=O)C=C1 JHNTXVXZXZPYQQ-UHFFFAOYSA-N 0.000 description 1
- JURKNVYFZMSNLP-UHFFFAOYSA-N Cyclobenzaprine Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 JURKNVYFZMSNLP-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N Picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000001430 anti-depressive Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960003572 cyclobenzaprine Drugs 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-M maleate(1-) Chemical compound OC(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940114148 picric acid Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229950002929 trinitrophenol Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US225864A US3306934A (en) | 1962-09-24 | 1962-09-24 | 5-(aminopropylidene)-and 5-hydroxy-5-(aminopropyl)-3-dialkylsulfamoyl-5h-dibenzo[a,d] cycloheptenes |
| US22586462 | 1962-09-24 | ||
| DEM0058228 | 1963-09-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1468283A1 DE1468283A1 (de) | 1968-11-28 |
| DE1468283C true DE1468283C (zh) | 1973-05-30 |
Family
ID=22846564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631468283 Granted DE1468283A1 (de) | 1962-09-24 | 1963-09-17 | Dibenzocycloheptene und Verfahren zu ihrer Herstellung |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3306934A (zh) |
| AT (1) | AT260203B (zh) |
| CH (2) | CH463494A (zh) |
| DE (1) | DE1468283A1 (zh) |
| DK (1) | DK119354B (zh) |
| ES (1) | ES292187A1 (zh) |
| FR (1) | FR3193M (zh) |
| GB (4) | GB1063523A (zh) |
| NL (2) | NL147726B (zh) |
| NO (1) | NO115799B (zh) |
| SE (2) | SE318271B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3458516A (en) * | 1968-02-16 | 1969-07-29 | American Cyanamid Co | 11-(piperazinyl)dibenz(b,f)(1,4)oxazepines and analogous thiazepines |
| US3903301A (en) * | 1973-02-28 | 1975-09-02 | Merck & Co Inc | Methods of treating muscular disorders |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686202A (en) * | 1951-03-19 | 1954-08-10 | Pennsylvania Salt Mfg Co | Production of aromatic sulfonyl fluorides |
| US2726265A (en) * | 1954-05-27 | 1955-12-06 | Du Pont | N-2-hydroxy-1-(p-sulfamylbenzoyl) ethylacylamides |
| FR1212723A (fr) * | 1958-01-09 | 1960-03-25 | Rhone Poulenc Sa | Nouveaux dérivés de la phénothiazine à chaîne carbamoylpipérazine et leur préparation |
| US3055890A (en) * | 1958-01-24 | 1962-09-25 | Rhone Poulenc Sa | Phenthiazine derivatives |
| NL240007A (zh) * | 1958-06-10 | |||
| US3073847A (en) * | 1959-02-12 | 1963-01-15 | Hoffmann La Roche | 9-(3-amino-1-propynyl) derivatives of 9-xanthenols and 9-thioxanthenols and a process for their preparation |
| NL108955C (zh) * | 1959-05-08 | |||
| US3082210A (en) * | 1959-10-29 | 1963-03-19 | Rhone Poulenc Sa | New 10-(azetidinyl-alkyl)phenthiazines |
-
0
- NL NL298304D patent/NL298304A/xx unknown
-
1962
- 1962-09-24 US US225864A patent/US3306934A/en not_active Expired - Lifetime
-
1963
- 1963-09-17 DE DE19631468283 patent/DE1468283A1/de active Granted
- 1963-09-18 AT AT751663A patent/AT260203B/de active
- 1963-09-20 GB GB5914/66A patent/GB1063523A/en not_active Expired
- 1963-09-20 GB GB37089/63A patent/GB1063521A/en not_active Expired
- 1963-09-20 GB GB5913/66A patent/GB1063522A/en not_active Expired
- 1963-09-20 GB GB5915/66A patent/GB1063524A/en not_active Expired
- 1963-09-21 NO NO150187A patent/NO115799B/no unknown
- 1963-09-23 DK DK447763AA patent/DK119354B/da unknown
- 1963-09-23 ES ES292187A patent/ES292187A1/es not_active Expired
- 1963-09-23 SE SE10372/63A patent/SE318271B/xx unknown
- 1963-09-24 NL NL63298304A patent/NL147726B/xx unknown
- 1963-09-24 CH CH184767A patent/CH463494A/de unknown
- 1963-09-24 CH CH1176163A patent/CH456578A/de unknown
- 1963-12-20 FR FR957991A patent/FR3193M/fr active Active
-
1966
- 1966-07-28 SE SE17804/66A patent/SE344588B/xx unknown
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