DE1174785B - Verfahren zur Herstellung von Azepinderivaten - Google Patents
Verfahren zur Herstellung von AzepinderivatenInfo
- Publication number
- DE1174785B DE1174785B DEG30935A DEG0030935A DE1174785B DE 1174785 B DE1174785 B DE 1174785B DE G30935 A DEG30935 A DE G30935A DE G0030935 A DEG0030935 A DE G0030935A DE 1174785 B DE1174785 B DE 1174785B
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- azepine
- parts
- lower alkyl
- compounds
- 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
- 150000001538 azepines Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000000950 dibromo group Chemical group Br* 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- -1 dibromo compound Chemical class 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000003047 N-acetyl group Chemical group 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RFLOWQIDXYCARJ-UHFFFAOYSA-N 1-(5-bromobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C1=C(Br)C2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 RFLOWQIDXYCARJ-UHFFFAOYSA-N 0.000 description 1
- OSQPHLCMJMVXLB-UHFFFAOYSA-N 1-(5H-dibenzo[b,f]azepin-5-yl)ethan-1-one Chemical compound C1=CC2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 OSQPHLCMJMVXLB-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
- HMTDVNGOTHWGDQ-UHFFFAOYSA-N 5-ethoxy-11h-benzo[b][1]benzazepine Chemical compound CCOC1=CC2=CC=CC=C2NC2=CC=CC=C12 HMTDVNGOTHWGDQ-UHFFFAOYSA-N 0.000 description 1
- ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 5-methoxy-11h-benzo[b][1]benzazepine Chemical compound COC1=CC2=CC=CC=C2NC2=CC=CC=C12 ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 0.000 description 1
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical class C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- SAPMCLVPWJEJLQ-UHFFFAOYSA-N CC(N1C(C=C(C=C2)Br)=C2C=CC2=C1C=CC=C2)=O Chemical compound CC(N1C(C=C(C=C2)Br)=C2C=CC2=C1C=CC=C2)=O SAPMCLVPWJEJLQ-UHFFFAOYSA-N 0.000 description 1
- PXMKDOCWVJJUKN-UHFFFAOYSA-N CCC(C=C1)=CC2=C1C=CC(C=CC=C1)=C1N2C(C)=O Chemical compound CCC(C=C1)=CC2=C1C=CC(C=CC=C1)=C1N2C(C)=O PXMKDOCWVJJUKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH8063559A CH376113A (de) | 1959-11-16 | 1959-11-16 | Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1174785B true DE1174785B (de) | 1964-07-30 |
Family
ID=4538107
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG30935A Pending DE1174785B (de) | 1959-11-16 | 1960-11-15 | Verfahren zur Herstellung von Azepinderivaten |
| DEG30937A Pending DE1161279B (de) | 1959-11-16 | 1960-11-15 | Verfahren zur Herstellung von Azepinonderivaten und deren Salzen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG30937A Pending DE1161279B (de) | 1959-11-16 | 1960-11-15 | Verfahren zur Herstellung von Azepinonderivaten und deren Salzen |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US3144442A (en, 2012) |
| CH (3) | CH376113A (en, 2012) |
| CY (1) | CY371A (en, 2012) |
| DE (2) | DE1174785B (en, 2012) |
| ES (2) | ES262487A1 (en, 2012) |
| GB (2) | GB943276A (en, 2012) |
| MY (1) | MY6700080A (en, 2012) |
| NL (4) | NL120689C (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI45449C (fi) * | 1965-04-29 | 1972-06-12 | Ciba Geigy Ag | Menetelmä uusien faramokologisesti aktiivisten 11-(1-piperatsinyyli)-d ibentso/b,f/tiepin-10(11H)-onien valmistamiseksi |
| US3968115A (en) * | 1970-02-05 | 1976-07-06 | Merck & Co., Inc. | 1-Alkyl-4-(10 and/or 11)-bromo-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-ylidene piperidine compounds |
| US4181655A (en) | 1973-08-24 | 1980-01-01 | Research Institute For Medicine And Chemistry Inc. | 5(3-Substituted aminopropyl)-10-trifluoromethoxy-5H-dibenz[b,f]azepines |
| US4603131A (en) * | 1982-04-26 | 1986-07-29 | Bernstein Joel E | Method and composition for treating and preventing irritation of the mucous membranes of the nose |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT200578B (de) * | 1956-11-13 | 1958-11-10 | Geigy Ag J R | Verfahren zur Herstellung von neuen N-Aminoalkylderivaten von Azepinen |
-
0
- NL NL121060D patent/NL121060C/xx active
- NL NL257977D patent/NL257977A/xx unknown
- NL NL257975D patent/NL257975A/xx unknown
- NL NL120689D patent/NL120689C/xx active
-
1959
- 1959-11-16 CH CH8063559A patent/CH376113A/de unknown
- 1959-11-16 CH CH8063459A patent/CH383977A/de unknown
- 1959-11-16 CH CH8063659A patent/CH377825A/de unknown
-
1960
- 1960-11-15 DE DEG30935A patent/DE1174785B/de active Pending
- 1960-11-15 ES ES0262487A patent/ES262487A1/es not_active Expired
- 1960-11-15 ES ES0262486A patent/ES262486A1/es not_active Expired
- 1960-11-15 DE DEG30937A patent/DE1161279B/de active Pending
- 1960-11-16 GB GB39269/60A patent/GB943276A/en not_active Expired
- 1960-11-16 GB GB3926860A patent/GB943275A/en not_active Expired - Lifetime
-
1962
- 1962-09-11 US US223301A patent/US3144442A/en not_active Expired - Lifetime
- 1962-09-11 US US223300A patent/US3144441A/en not_active Expired - Lifetime
- 1962-09-11 US US223302A patent/US3144443A/en not_active Expired - Lifetime
-
1967
- 1967-02-24 CY CY37167A patent/CY371A/xx unknown
- 1967-12-31 MY MY196780A patent/MY6700080A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH383977A (de) | 1964-11-15 |
| NL120689C (en, 2012) | |
| CH376113A (de) | 1964-03-31 |
| US3144441A (en) | 1964-08-11 |
| GB943275A (en, 2012) | |
| NL257975A (en, 2012) | |
| ES262487A1 (es) | 1961-06-01 |
| CY371A (en) | 1967-02-24 |
| ES262486A1 (es) | 1961-06-01 |
| NL121060C (en, 2012) | |
| NL257977A (en, 2012) | |
| CH377825A (de) | 1964-05-31 |
| US3144442A (en) | 1964-08-11 |
| DE1161279B (de) | 1964-01-16 |
| MY6700080A (en) | 1967-12-31 |
| GB943276A (en) | 1963-12-04 |
| US3144443A (en) | 1964-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2265370C2 (de) | 6-Phenyl-1,2,3,4-tetrahydro-1,5-benzodiazocinderivate | |
| DE1014551B (de) | Verfahren zur Herstellung von substituierten 4-Oxycumarinen | |
| DE2243550B2 (de) | OrganosUicium- und Organogermaniumverbindungen und sie enthaltende Arzneimittel | |
| DE1174785B (de) | Verfahren zur Herstellung von Azepinderivaten | |
| DE1104965B (de) | Verfahren zur Herstellung von Derivaten des Urazols | |
| DE1138057B (de) | Verfahren zur Herstellung von 1-Phenyl-2, 3-dimethyl-4-morpholino-methyl-pyrazolon-(5)-derivaten | |
| DE1518771A1 (de) | Verfahren zur Herstellung von 2-(Dialkylmethyl)-5-alkyl-2-cyclohexen-1-onen | |
| AT219050B (de) | Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen | |
| DE1135465B (de) | Verfahren zur Herstellung von 2, 2-Bis-(p-hydroxyphenyl)-3-oxo-dihydrobenzoxazinen-(1, 4) und deren O-Acyl- bzw. O-Alkylderivaten | |
| DE1695893B1 (de) | Verfahren zur Herstellung von 4-Amino-5-acylamidomethylpyrimidinen | |
| AT287726B (de) | Verfahren zur Herstellung von neuen 1H-Thieno-[3,2-e]-1,4-diazepin-2-onen sowie ihren N-Oxyden und Salzen | |
| DE1168918B (de) | Verfahren zur Herstellung von Acylanthranilsaeureaniliden | |
| DE2701629C2 (en, 2012) | ||
| AT251770B (de) | Verfahren zur Herstellung von neuen, basisch substituierten, therapeutisch wirksmen Steroidverbindungen | |
| DE2010124C (de) | Verfahren zur Herstellung von 2 6 Dimethyl 3 amino 6 (beta cyanoathyl) cyclo hexen (2) on | |
| DE859166C (de) | Verfahren zur Herstellung von Benz-(cd)-indolinen | |
| DE1092927B (de) | Verfahren zur Herstellung von 4,6-Diacyl-1,3-dioxybenzolen | |
| AT349030B (de) | Verfahren zur herstellung von neuen 8-hydroxy- 3-halogenmethyl-4-acetoxy-10-methylen-2,9- dioxatricyclo(4,3,1,03,7)decanen bzw. der entsprechenden 8-oxo-derivate | |
| AT273132B (de) | Verfahren zur Herstellung von neuen Pyridyl-tetrahydroisochinolinen sowie von deren Säureaddtionssalzen | |
| CH448085A (de) | Verfahren zur Herstellung von Pyridinderivaten | |
| DE2222833A1 (de) | Cyclopenteno-chinolonderivate und verfahren zur herstellung derselben | |
| DE1078578B (de) | Verfahren zur Herstellung von Theophyllinderivaten | |
| DE1695381B2 (de) | Phthalazino eckige klammer auf 2,3-b eckige klammer zu phthalazine und ein verfahren zu ihrer herstellung | |
| DE1142870B (de) | Verfahren zur Herstellung von Azepinderivaten | |
| DE1203253B (de) | Verfahren zur Herstellung basischer Fluorenderivate und ihrer Salze |