GB1114970A - New azepine derivatives and their production - Google Patents
New azepine derivatives and their productionInfo
- Publication number
- GB1114970A GB1114970A GB5740166A GB5740166A GB1114970A GB 1114970 A GB1114970 A GB 1114970A GB 5740166 A GB5740166 A GB 5740166A GB 5740166 A GB5740166 A GB 5740166A GB 1114970 A GB1114970 A GB 1114970A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- dibenz
- azepine
- dihydro
- compound
- 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
- 150000001538 azepines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 2
- PHZJTKVENKBEPK-UHFFFAOYSA-N 1-(2-ethylsulfanyl-5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C(C)SC=1C=CC2=C(N(C3=C(CC2)C=CC=C3)C(C)=O)C1 PHZJTKVENKBEPK-UHFFFAOYSA-N 0.000 abstract 1
- VXZKQJRIAVBAKW-UHFFFAOYSA-N 1-(2-ethylsulfinyl-5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C(C)S(=O)C=1C=CC2=C(N(C3=C(CC2)C=CC=C3)C(C)=O)C1 VXZKQJRIAVBAKW-UHFFFAOYSA-N 0.000 abstract 1
- REABGEVKWMWITC-UHFFFAOYSA-N 11-(3-chloropropyl)-2-methylsulfinyl-5,6-dihydrobenzo[b][1]benzazepine Chemical compound CS(=O)C=1C=CC2=C(N(C3=C(CC2)C=CC=C3)CCCCl)C1 REABGEVKWMWITC-UHFFFAOYSA-N 0.000 abstract 1
- OUJMUPGOEUYVNF-UHFFFAOYSA-N 2-ethylsulfinyl-6,11-dihydro-5H-benzo[b][1]benzazepine Chemical compound C(C)S(=O)C=1C=CC2=C(NC3=C(CC2)C=CC=C3)C1 OUJMUPGOEUYVNF-UHFFFAOYSA-N 0.000 abstract 1
- DOMIIJMZTSKSPV-UHFFFAOYSA-N 2-methylsulfinyl-6,11-dihydro-5H-benzo[b][1]benzazepine Chemical compound CS(=O)C=1C=CC2=C(NC3=C(CC2)C=CC=C3)C1 DOMIIJMZTSKSPV-UHFFFAOYSA-N 0.000 abstract 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 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
- C07D223/28—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a single bond between positions 10 and 11
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
<FORM:1114970/C2/1> <FORM:1114970/C2/2> <FORM:1114970/C2/3> <FORM:1114970/C2/4> <FORM:1114970/C2/5> <FORM:1114970/C2/6> Novel dibenzazepines of the Formula I, wherein R1 represents a C1- 4 alkyl group, each of R2 and R3 represents hydrogen or a C1- 4 alkyl group and R4 represents a C1- 4 alkyl group or, when taken together with R2, it represents an alkylene group having (3-n) or (4-n) chain members, or, together with R3, it represents an alkylene group having 4 to 6 chain members, m represents 1 or 2, n represents 0, 1 or 2 and (m + n) represents 1,2 or 3, and their acid addition salts, are prepared by (a) reacting a compound of the Formula II with an oxidizing agent, or (b) reacting a compound of the Formula III in the presence of a basic condensing agent, with a reactive ester of an amino alcohol of the Formula IV, wherein R31 represents a C1- 4 alkyl group, or (c) reacting a reactive ester of an alcohol of the Formula V with an amine of the formula HNR3R4 or (d) hydrolysing a compound of the Formula VI, wherein R5 represents a cyano group or an acyl radical of a carboxylic acid or of a monofunctional derivative of carbonic acid, and, if desired, converting a compound of Formula I obtained by any of methods (a) to (d) into an acid addition salt. 3-Methylsulphinyl- or 3-ethylsulphinyl-10,11-dihydro - 5H - dibenz[b,f]azepine is prepared by oxidizing 3-methylthio- or 3-ethylthio-5-acetyl-10,11 - dihydro - 5H - dibenz[b,f]azepine with sodium metaperiodate and hydrolysing the resulting 3 - methylsulphinyl- or 3 - ethylsulphinyl - 5 - acetyl - 10,11 - dihydro - 5H - dibenz[b,f]azepine with potassium hydroxide in ethanol. 3 - Methylsulphinyl - 5 - (3 - chloropropyl) - 10,11 - dihydro - 5H - dibenz[b,f]azepine is prepared by reacting 3-methylsulphinyl-10,11-dihydro - 5H - dibenz[b,f]azepine with 1-chloro-3-bromo-propane. Pharmaceutical compositions, having chatecholamine-potentiating and reserpine-antagonistic activity, for oral, rectal or parenteral administration, comprise a compound of Formula I together with a carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1774965A CH454875A (en) | 1965-12-23 | 1965-12-23 | Process for the production of new azepine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1114970A true GB1114970A (en) | 1968-05-22 |
Family
ID=4427789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5740166A Expired GB1114970A (en) | 1965-12-23 | 1966-12-22 | New azepine derivatives and their production |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT268289B (en) |
| BE (1) | BE691640A (en) |
| CH (1) | CH454875A (en) |
| DE (1) | DE1695002A1 (en) |
| DK (1) | DK122764B (en) |
| ES (1) | ES334817A1 (en) |
| FI (1) | FI44236B (en) |
| FR (1) | FR1506734A (en) |
| GB (1) | GB1114970A (en) |
| IL (1) | IL27124A (en) |
| NL (1) | NL6618038A (en) |
| NO (1) | NO118920B (en) |
| SE (1) | SE333736B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931151A (en) * | 1972-10-09 | 1976-01-06 | Roussel-Uclaf | Dibenzo (b,f) azepines |
-
1965
- 1965-12-23 CH CH1774965A patent/CH454875A/en unknown
-
1966
- 1966-12-16 FI FI334866A patent/FI44236B/fi active
- 1966-12-22 DE DE19661695002 patent/DE1695002A1/en active Pending
- 1966-12-22 SE SE1757566A patent/SE333736B/xx unknown
- 1966-12-22 AT AT1180666A patent/AT268289B/en active
- 1966-12-22 BE BE691640D patent/BE691640A/xx unknown
- 1966-12-22 DK DK663366A patent/DK122764B/en unknown
- 1966-12-22 NL NL6618038A patent/NL6618038A/xx unknown
- 1966-12-22 ES ES334817A patent/ES334817A1/en not_active Expired
- 1966-12-22 NO NO16611866A patent/NO118920B/no unknown
- 1966-12-22 IL IL2712466A patent/IL27124A/en unknown
- 1966-12-22 GB GB5740166A patent/GB1114970A/en not_active Expired
- 1966-12-23 FR FR88632A patent/FR1506734A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931151A (en) * | 1972-10-09 | 1976-01-06 | Roussel-Uclaf | Dibenzo (b,f) azepines |
Also Published As
| Publication number | Publication date |
|---|---|
| SE333736B (en) | 1971-03-29 |
| NO118920B (en) | 1970-03-02 |
| DE1695002A1 (en) | 1971-03-25 |
| BE691640A (en) | 1967-06-22 |
| CH454875A (en) | 1968-04-30 |
| NL6618038A (en) | 1967-06-26 |
| AT268289B (en) | 1969-02-10 |
| FI44236B (en) | 1971-06-30 |
| DK122764B (en) | 1972-04-10 |
| ES334817A1 (en) | 1968-03-01 |
| IL27124A (en) | 1970-10-30 |
| FR1506734A (en) | 1967-12-22 |
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