GB1465032A - N,n-diethyl-dibenzo-b,e thiepin-11-6h-ylidene-1,3-propane diamine derivatives methods for their preparation and compo sitions containing them - Google Patents
N,n-diethyl-dibenzo-b,e thiepin-11-6h-ylidene-1,3-propane diamine derivatives methods for their preparation and compo sitions containing themInfo
- Publication number
- GB1465032A GB1465032A GB1142975A GB1142975A GB1465032A GB 1465032 A GB1465032 A GB 1465032A GB 1142975 A GB1142975 A GB 1142975A GB 1142975 A GB1142975 A GB 1142975A GB 1465032 A GB1465032 A GB 1465032A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- thiepin
- dibenzo
- diethyl
- propanediamine
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
Abstract
1465032 N,N - Diethyl N<SP>1</SP> - [dibenzo[b,e]- thiepin - 11(6H) - ylidene] - 1,3 - propanediamine derivatives F HOFFMANN-LA ROCHE & CO AG 19 March 1975 [20 March 1974] 11429/75 Heading C2C Novel compounds I and their acid addition salts in which X is S or SO 2 and R is H or Me, are prepared by (1) reacting a compound II with NH 2 -(CH 2 ) 3 -NEt 2 in the presence of a dehydrating agent (2) reacting a compound III in which Y is a leaving atom or group with HNEt 2 to form a compound I (X = S) (3) deoxygenating the corresponding N<SP>1</SP>-oxide (4) dehydrogenating the corresponding N,N-diethyl- N<SP>1</SP>[R - substituted - dibenzo[6,e]thiepin- 11- (6H)-yl]-1,3-propanediamine to form a compound I (X = S) or (5) ethylating the corresponding N-monoethyl compound; and if desired converting a compound I formed into an acid addition salt. Compounds III (Y = tosyloxy) are prepared by reacting: a Compound II with 3-amino-1- propanol and treating the imino-propanol formed with tosyl chloride, N,N-diethyl-N- [dibenzo[b,e]thiepin - 11(6H) - ylidene) - 1,3- propanediamine - N<SP>1</SP> - oxide and N<SP>1</SP> - 5,5- trioxide are prepared from the corresponding compound II (R = H) by the formation of the oxime which is reacted with Cl(CH 2 ) 3 NEt 2 . N,N - Diethyl - N<SP>1</SP> - [dibenzo[b,e]thiepin - 11(6H)- yl]-1,3-propanediamine is prepared by reducing a compound II (R = H, X = S) to the alcohol, chlorinating to give the 11-chloro compound which is reacted with 1,3-propanediamine. NEthyl - N<SP>1</SP> - [dibenzo[b,e]thiepin - 11(6H) - yl]- 1,3-propandiane and its 5-oxide are prepared from the corresponding compound II (R = H) and N-ethyl-1,3-propanediamine. Compounds I are diuretics and form with a carrier a pharmaceutical composition which may be administered orally. Reference has been directed by the Comptroller to Specification 1,334,967.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH387974A CH596204A5 (en) | 1974-03-20 | 1974-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1465032A true GB1465032A (en) | 1977-02-16 |
Family
ID=4265453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1142975A Expired GB1465032A (en) | 1974-03-20 | 1975-03-19 | N,n-diethyl-dibenzo-b,e thiepin-11-6h-ylidene-1,3-propane diamine derivatives methods for their preparation and compo sitions containing them |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS50126687A (en) |
| AR (1) | AR212800A1 (en) |
| AT (1) | AT345837B (en) |
| BE (1) | BE826860A (en) |
| CH (1) | CH596204A5 (en) |
| DD (1) | DD118430A5 (en) |
| DE (1) | DE2512046A1 (en) |
| DK (1) | DK113075A (en) |
| FI (1) | FI750809A (en) |
| FR (1) | FR2264550B1 (en) |
| GB (1) | GB1465032A (en) |
| IL (1) | IL46746A (en) |
| LU (1) | LU72080A1 (en) |
| NL (1) | NL7503137A (en) |
| NO (1) | NO750945L (en) |
| PH (1) | PH11232A (en) |
| SE (1) | SE7503004L (en) |
| SU (1) | SU563122A3 (en) |
| ZA (1) | ZA751339B (en) |
-
1974
- 1974-03-20 CH CH387974A patent/CH596204A5/xx not_active IP Right Cessation
-
1975
- 1975-03-04 IL IL46746A patent/IL46746A/en unknown
- 1975-03-04 ZA ZA00751339A patent/ZA751339B/en unknown
- 1975-03-13 AR AR257954A patent/AR212800A1/en active
- 1975-03-14 PH PH16910A patent/PH11232A/en unknown
- 1975-03-17 NL NL7503137A patent/NL7503137A/en not_active Application Discontinuation
- 1975-03-17 SE SE7503004A patent/SE7503004L/xx unknown
- 1975-03-18 SU SU2114299A patent/SU563122A3/en active
- 1975-03-18 DD DD184846A patent/DD118430A5/xx unknown
- 1975-03-18 FR FR7508380A patent/FR2264550B1/fr not_active Expired
- 1975-03-18 LU LU72080A patent/LU72080A1/xx unknown
- 1975-03-19 NO NO750945A patent/NO750945L/no unknown
- 1975-03-19 FI FI750809A patent/FI750809A/fi not_active Application Discontinuation
- 1975-03-19 GB GB1142975A patent/GB1465032A/en not_active Expired
- 1975-03-19 BE BE154482A patent/BE826860A/en unknown
- 1975-03-19 AT AT211675A patent/AT345837B/en not_active IP Right Cessation
- 1975-03-19 DE DE19752512046 patent/DE2512046A1/en active Pending
- 1975-03-19 JP JP50033470A patent/JPS50126687A/ja active Pending
- 1975-03-19 DK DK113075A patent/DK113075A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FI750809A (en) | 1975-09-21 |
| NL7503137A (en) | 1975-09-23 |
| IL46746A (en) | 1978-06-15 |
| BE826860A (en) | 1975-09-19 |
| IL46746A0 (en) | 1975-05-22 |
| FR2264550B1 (en) | 1978-07-28 |
| LU72080A1 (en) | 1977-01-31 |
| SE7503004L (en) | 1975-09-22 |
| AT345837B (en) | 1978-10-10 |
| DK113075A (en) | 1975-09-21 |
| AR212800A1 (en) | 1978-10-13 |
| ATA211675A (en) | 1978-02-15 |
| FR2264550A1 (en) | 1975-10-17 |
| NO750945L (en) | 1975-09-23 |
| DD118430A5 (en) | 1976-03-05 |
| JPS50126687A (en) | 1975-10-04 |
| CH596204A5 (en) | 1978-03-15 |
| ZA751339B (en) | 1976-02-25 |
| AU7896875A (en) | 1976-09-16 |
| SU563122A3 (en) | 1977-06-25 |
| PH11232A (en) | 1977-10-28 |
| DE2512046A1 (en) | 1975-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |