DE1133729B - Verfahren zur Herstellung von 5-{ª†-(4'-Hydroxyaethylpiperazino)-propyl}-dibenzo[b, f]azepin - Google Patents
Verfahren zur Herstellung von 5-{ª†-(4'-Hydroxyaethylpiperazino)-propyl}-dibenzo[b, f]azepinInfo
- Publication number
- DE1133729B DE1133729B DEG30349A DEG0030349A DE1133729B DE 1133729 B DE1133729 B DE 1133729B DE G30349 A DEG30349 A DE G30349A DE G0030349 A DEG0030349 A DE G0030349A DE 1133729 B DE1133729 B DE 1133729B
- Authority
- DE
- Germany
- Prior art keywords
- azepine
- dibenzo
- formula
- propyl
- parts
- 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.)
- Pending
Links
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- KDUIIIUHZIHOHE-UHFFFAOYSA-N 11-(3-piperazin-1-ylpropyl)benzo[b][1]benzazepine Chemical compound C12=CC=CC=C2C=CC2=CC=CC=C2N1CCCN1CCNCC1 KDUIIIUHZIHOHE-UHFFFAOYSA-N 0.000 claims description 2
- 150000004885 piperazines Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- BYWPWUMQXKGILM-UHFFFAOYSA-N 11-(3-chloropropyl)benzo[b][1]benzazepine Chemical compound C1=CC2=CC=CC=C2N(CCCCl)C2=CC=CC=C21 BYWPWUMQXKGILM-UHFFFAOYSA-N 0.000 description 1
- IFRKEAUJMRIYNC-UHFFFAOYSA-N 2-piperazin-1-ylethyl acetate Chemical compound CC(=O)OCCN1CCNCC1 IFRKEAUJMRIYNC-UHFFFAOYSA-N 0.000 description 1
- CXHRHQJOTCKDBC-UHFFFAOYSA-N 3-benzo[b][1]benzazepin-11-ylpropan-1-ol Chemical compound OCCCN1C(C=CC=C2)=C2C=CC2=C1C=CC=C2 CXHRHQJOTCKDBC-UHFFFAOYSA-N 0.000 description 1
- LWEOFVINMVZGAS-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-ol Chemical compound OCCCN1CCNCC1 LWEOFVINMVZGAS-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- -1 N-substituted piperazine Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000003756 stirring Methods 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
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/26—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a double bond between positions 10 and 11
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4591057A CH364263A (de) | 1957-05-09 | 1957-05-09 | Verfahren zur Herstellung von basisch substituierten Azepinen |
| CH5833258A CH366542A (de) | 1957-05-09 | 1958-04-15 | Verfahren zur Herstellung von basischen Derivaten von Azepinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1133729B true DE1133729B (de) | 1962-07-26 |
Family
ID=25737647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG30349A Pending DE1133729B (de) | 1957-05-09 | 1958-05-08 | Verfahren zur Herstellung von 5-{ª†-(4'-Hydroxyaethylpiperazino)-propyl}-dibenzo[b, f]azepin |
Country Status (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996015113A1 (en) * | 1994-11-09 | 1996-05-23 | Taro Pharmaceutical Industries, Ltd. | Preparation of n-(3-halopropyl)iminostilbene and its conversion to opipramol |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947447A (en) * | 1974-05-20 | 1976-03-30 | American Hoechst Corporation | 5H-aminoacetamido-10,11-dihydrodibenz-[b,f]azepines and immediate precursors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE549299A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1955-10-20 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2541211A (en) * | 1948-10-15 | 1951-02-13 | Searle & Co | Tertiary-aminoalkyl-tetrahydrocarbazoles |
| US2676966A (en) * | 1951-04-04 | 1954-04-27 | Searle & Co | Quaternary salts of 9-carbazolealkylamines and 10-acridanalkylamines and methods forpreparing same |
| US2676971A (en) * | 1951-04-21 | 1954-04-27 | Searle & Co | Quaternary ammonium derivatives of aminoalkylxanthenes and aminoalkylthiaxanthenes |
| US2861987A (en) * | 1955-12-28 | 1958-11-25 | Cilag Ltd | New diphenyl methane- and 1-aza-[2,3:5,6]-dibenzocy cloheptadiene derivatives, theiracid salts and quaternary salts and the production thereof |
-
1957
- 1957-05-09 CH CH4591057A patent/CH364263A/de unknown
- 1957-05-09 CH CH360061D patent/CH360061A/de unknown
- 1957-05-09 CH CH359143D patent/CH359143A/de unknown
-
1958
- 1958-04-15 CH CH5833258A patent/CH366542A/de unknown
- 1958-05-07 FR FR765074A patent/FR1226426A/fr not_active Expired
- 1958-05-08 NL NL227620A patent/NL103879C/xx active
- 1958-05-08 DE DEG30349A patent/DE1133729B/de active Pending
- 1958-05-08 GB GB14737/58A patent/GB862297A/en not_active Expired
- 1958-05-08 BE BE567519D patent/BE567519A/xx unknown
-
1959
- 1959-08-10 US US832498A patent/US3133068A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE549299A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1955-10-20 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996015113A1 (en) * | 1994-11-09 | 1996-05-23 | Taro Pharmaceutical Industries, Ltd. | Preparation of n-(3-halopropyl)iminostilbene and its conversion to opipramol |
| US5599929A (en) * | 1994-11-09 | 1997-02-04 | Taro Pharmaceutical Industries Ltd | Method for preparing opipramol |
| CN1068312C (zh) * | 1994-11-09 | 2001-07-11 | 塔罗制药工业有限公司 | 羟乙哌䓬的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL103879C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1963-02-15 |
| FR1226426A (fr) | 1960-07-11 |
| CH366542A (de) | 1963-01-15 |
| GB862297A (en) | 1961-03-08 |
| CH364263A (de) | 1962-09-15 |
| CH360061A (de) | 1962-02-15 |
| CH359143A (de) | 1961-12-31 |
| US3133068A (en) | 1964-05-12 |
| BE567519A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1958-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0007019A1 (de) | Neue 5-Phenylpyrazol-Derivate und ihre Salze; Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| CH345342A (de) | Verfahren zur Herstellung neuer basisch substituierter Heterocyclen | |
| DE1037461B (de) | Verfahren zur Herstellung von Phenthiazinderivaten | |
| DE2147023B2 (de) | Verfahren zur Herstellung von 1H- Tetrazol-Verbindungen | |
| DE1147947B (de) | Verfahren zur Herstellung neuer 1, 2-Benzisothiazolone | |
| DE1133729B (de) | Verfahren zur Herstellung von 5-{ª†-(4'-Hydroxyaethylpiperazino)-propyl}-dibenzo[b, f]azepin | |
| AT202152B (de) | Verfahren zur Herstellung von neuen Dimethylaminopropylidenthiaxanthenen. | |
| DE1246722B (de) | Verfahren zur Herstellung von Harnstoffderivaten | |
| DE1952019B2 (de) | Verfahren zur Herstellung von 5,6 Dihydrodibenz eckige Klammer auf b,f ecki ge Klammer zu azocin Derivaten | |
| DE2814347A1 (de) | Verfahren zur herstellung von steroidsaeuren | |
| AT235293B (de) | Verfahren zur Herstellung von neuen Piperidinderivaten | |
| AT200579B (de) | Verfahren zur Herstellung der neuen 5-Dibenzo[b,f]azepine | |
| AT211829B (de) | Verfahren zur Herstellung von neuen 3-Aminothiophen-2-carbonsäureestern und den entsprechenden freien Carbonsäuren | |
| AT205038B (de) | Verfahren zur Herstellung neuer, in 10-Stellung substituierter 11-Oxo-dibenzo-[b, f]-thia-[1]-aza-[4]-cycloheptadien-[2,6]-Verbindungen | |
| AT228794B (de) | Verfahren zur Herstellung von N-heterocyclischen Verbindungen | |
| DE1132556B (de) | Verfahren zur Herstellung von Derivaten des 5-(ª†-Piperazino-propyl)-dibenzo[b, f]azepins | |
| DE1161279B (de) | Verfahren zur Herstellung von Azepinonderivaten und deren Salzen | |
| AT268321B (de) | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen und ihren Salzen | |
| AT268323B (de) | Verfahren zur Herstellung von neuen 3,1-Benzothiazin-Derivaten und ihren Salzen | |
| AT359497B (de) | Verfahren zur herstellung von neuen 8-(tetrazol -5-ylcarbamoyl)-chinolinderivaten und ihren salzen | |
| AT219613B (de) | Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen und deren Salzen | |
| AT226696B (de) | Verfahren zur Herstellung von neuen Derivaten des Phthalimidins bzw. deren quaternären Ammoniumverbindungen | |
| AT223189B (de) | Verfahren zur Herstellung von neuen Aryloxyessigsäureamiden | |
| AT300785B (de) | Verfahren zur Herstellung von neuen 1-Β-Phenylpropioloyl-3-indolylessigsäurederivaten | |
| DE1246742B (de) | Verfahren zur Herstellung von neuen Phenothiazinen |