GB1180164A - Dibenzazepine Derivatives and their preparation - Google Patents
Dibenzazepine Derivatives and their preparationInfo
- Publication number
- GB1180164A GB1180164A GB2858/68A GB285868A GB1180164A GB 1180164 A GB1180164 A GB 1180164A GB 2858/68 A GB2858/68 A GB 2858/68A GB 285868 A GB285868 A GB 285868A GB 1180164 A GB1180164 A GB 1180164A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compound
- hydrogen
- phenylalkyl
- methyl
- 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
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Combustion Methods Of Internal-Combustion Engines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Securing Globes, Refractors, Reflectors Or The Like (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
1,180,164. Dibenzazepine derivatives. RHONE-POULENC S.A. 18 Jan., 1968 [18 Jan., 1967; 9 Nov., 1967], No. 2858/68. Heading C2C. Novel compounds of Formula I in which each of R and R<SP>1</SP> is hydrogen, alkyl, hydroxyalkyl, hydroxy alkoxy alkyl, phenylalkyl, or phenylalkyl substituted in the phenyl nucleus by one or more of halogen, alkyl, alkoxy, nitro, amino or trifluoromethyl, and R 1 is hydrogen, alkyl, phenylalkyl or phenylalkyl substituted in the phenyl nucleus by one or more of halogen, alkyl, alkoxy or trifluoromethyl, and acid addition salts and quaternary ammonium derivatives thereof, are prepared (a) for compounds I in which both of R and R<SP>1</SP> are hydrogen, by reducing a compound of Formula II; or (b) for compounds I in which -NRR<SP>1</SP> is -N(R 3 )CH 2 R 2 , in which R 2 is hydrogen, C 1-4 alkyl, C 1-4 hydroxyalkyl, hydroxy-C 1-4 alkoxy- C 1-4 alkyl, phenyl, phenyl-C 1-4 alkyl, or phenyl- C 1-4 alkyl in which the phenyl nucleus is substituted by one or more of halogen, alkyl, alkoxy, amino or trifluoromethyl, and R 3 is hydrogen, alkyl, phenylalkyl or phenylalkyl substituted in the phenyl nucleus by one or more of halogen, C 1-5 alkyl or trifluoromethyl, by reducing a compound of Formula III, or (c) for compounds I in which -NRR<SP>1</SP> is or -N(CH 2 -R 2 ) 2 ; in which R 4 is hydrogen, alkyl, hydroxyalkyl, hydroxyalkoxyalkyl, phenylalkyl or phenylalkyl substituted by one or more of halogen, alkyl, alkoxy, amino or trifluoromethyl, by reacting a compound of formula R 2 -CHO and hydrogen in the presence of a hydrogenation catalyst with a compound of Formula V or VI, in which Ac is an acyl radical which can be readily eliminated by acid hydrolysis, and, if necessary, eliminating the Ac radical by hydrolysis to form a compound I, in which R 1 is hydrogen; or (d) for compounds I in which -NRR<SP>1</SP> is -NRR 5 or -N(R 5 ) 2 , in which R 5 is alkyl, hydroxyalkyl, hydroxyalkoxyalkyl, phenylalkyl or phenylalkyl substituted by one or more of halogen, alkyl, alkoxy, nitro, amino or trifluoromethyl, by reacting a compound of formula R 5 -X, in which X is a reactive ester residue, with a compound of Formula VIII; or (e) for compounds I in which -NRR<SP>1</SP> is -NH-R 5 , by replacing, in a compound of Formula VIII, in which Y is cyano, alkoxycarbonyl, alkanoyl, alkane sulphonyl or arylsulphonyl, the radical Y by a hydrogen atom; or (f) for compounds I in which -NRR<SP>1</SP> is -N(R 6 )-CH 3 , in which R 6 is hydrogen or alkyl, by reducing a compound of Formula IX, in which R 7 is alkyl, and, if desired, converting a compound obtained by any of methods (a) to (f) into an acid addition salt or quaternary ammonium derivative. The alkyl and alkoxy groups referred to in the above definitions contain 1 to 5 carbon atoms unless otherwise stated. Starting materials.-5-Methyl-10-formamido-, acetylamino -, (N - acetyl - N - ethylamino) -, (N - formyl - N - ethylamino) - and (N - ethoxycarbonyl - N - ethylamino) - 10,11 - dihydrodibenzo[b,f]azepines are prepared by acylation of the corresponding amino compounds. 5- Methyl - 10 - (N - formyl - N - methylamino) - 10,11-dihydrodibenzo[b, f]azepine is prepared by methylation of 5-methyl-10-formamido-10,11- dihydrodibenzo[b,f]azepine. 5 - Methyl - 10- (N - methyl - N - tosylamino) - 10,11 - dihydrodibenzo[b,f]azepine is prepared by reacting ptoluenesulphonyl chloride with 5-methyl-10 - amino - 10,11 - dihydrodibenzo[b,f]azepine to give 5 - methyl - 10 - tosylamino - 10,11 - dihydrodibenzo[b,f]azepine and reacting this with dimothylsulphate. 5 - Methyl - 10 - (N - cyano- N - methylamino) 10,11 - dihydrodibenzo[b,f] azepine is prepared by reacting the corresponding 10-dimethylamino compound with cyanogen bromide. Pharmaceutical compositions having antidepressant, analgesic, anticonvulsant and tranquillizing activity, for oral, parenteral or rectal administration, comprise a compound I, or a pharmaceutically acceptable acid addition or quaternary ammonium derivative thereof, together with a pharmaceutically acceptable carrier or coating.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR91646A FR1532301A (en) | 1967-01-18 | 1967-01-18 | New derivatives of dibenzazepine and their preparation |
| FR127611A FR94320E (en) | 1967-01-18 | 1967-11-09 | New dibenzazepine derivatives and their preparation. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1180164A true GB1180164A (en) | 1970-02-04 |
Family
ID=26174548
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23183/69A Expired GB1180165A (en) | 1967-01-18 | 1968-01-18 | Novel Ketoximes and their preparation |
| GB2858/68A Expired GB1180164A (en) | 1967-01-18 | 1968-01-18 | Dibenzazepine Derivatives and their preparation |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23183/69A Expired GB1180165A (en) | 1967-01-18 | 1968-01-18 | Novel Ketoximes and their preparation |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3622565A (en) |
| AT (6) | AT281842B (en) |
| BE (1) | BE709523A (en) |
| CH (1) | CH482677A (en) |
| DE (1) | DE1695666C3 (en) |
| DK (2) | DK120950B (en) |
| ES (5) | ES349459A1 (en) |
| FI (1) | FI48927C (en) |
| FR (2) | FR1532301A (en) |
| GB (2) | GB1180165A (en) |
| IE (1) | IE31926B1 (en) |
| IL (1) | IL29340A (en) |
| LU (1) | LU55297A1 (en) |
| NL (1) | NL156137B (en) |
| NO (2) | NO125677B (en) |
| OA (1) | OA03401A (en) |
| SE (2) | SE350971B (en) |
| SU (1) | SU464112A3 (en) |
| YU (2) | YU32142B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3882235A (en) * | 1969-06-24 | 1975-05-06 | Rhone Poulenc Sa | Fungicidal compositions comprising A 10, 11 dihydrodibenzo {8 b,f{9 {0 azepine derivative |
| FR2198942B1 (en) * | 1972-09-12 | 1975-03-14 | Rhone Poulenc Ind | |
| FI75561C (en) * | 1979-10-30 | 1988-07-11 | Ciba Geigy Ag | Process for the preparation of 5-carbamoyl-10-oxo-10,11-dihydro-5H-di benz / b, f / azepine and necessary intermediates thereto. |
| NZ568694A (en) | 2005-11-09 | 2011-09-30 | Zalicus Inc | Method, compositions, and kits for the treatment of medical conditions |
| MX2010005813A (en) | 2007-11-28 | 2010-06-15 | Nektar Therapeutics | Oligomer-tricyclic conjugates. |
| WO2011091050A1 (en) | 2010-01-19 | 2011-07-28 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
| JP6002144B2 (en) | 2010-12-10 | 2016-10-05 | ネクター セラピューティクス | Hydroxylated tricyclic compounds |
| EP3856196B1 (en) | 2018-09-28 | 2023-11-15 | Griffith University | Phenylpropionic acid derivatives for modulating pathogen activity |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH457447A (en) * | 1965-07-26 | 1968-06-15 | Geigy Ag J R | Process for the production of new azepine derivatives |
-
1967
- 1967-01-18 FR FR91646A patent/FR1532301A/en not_active Expired
- 1967-11-09 FR FR127611A patent/FR94320E/en not_active Expired
-
1968
- 1968-01-09 OA OA53156A patent/OA03401A/en unknown
- 1968-01-10 NL NL6800363.A patent/NL156137B/en not_active IP Right Cessation
- 1968-01-16 SE SE04482/70A patent/SE350971B/xx unknown
- 1968-01-16 SE SE00553/68A patent/SE338995B/xx unknown
- 1968-01-16 DK DK15068AA patent/DK120950B/en not_active IP Right Cessation
- 1968-01-16 FI FI680114A patent/FI48927C/en active
- 1968-01-17 IL IL29340A patent/IL29340A/en unknown
- 1968-01-17 BE BE709523A patent/BE709523A/en unknown
- 1968-01-17 LU LU55297D patent/LU55297A1/xx unknown
- 1968-01-17 NO NO0200/68A patent/NO125677B/no unknown
- 1968-01-17 IE IE57/68A patent/IE31926B1/en unknown
- 1968-01-17 US US698436A patent/US3622565A/en not_active Expired - Lifetime
- 1968-01-18 AT AT03858/69A patent/AT281842B/en not_active IP Right Cessation
- 1968-01-18 ES ES349459A patent/ES349459A1/en not_active Expired
- 1968-01-18 CH CH76368A patent/CH482677A/en not_active IP Right Cessation
- 1968-01-18 GB GB23183/69A patent/GB1180165A/en not_active Expired
- 1968-01-18 DE DE1695666A patent/DE1695666C3/en not_active Expired
- 1968-01-18 AT AT386169A patent/AT279632B/en not_active IP Right Cessation
- 1968-01-18 AT AT03860/69A patent/AT279631B/en not_active IP Right Cessation
- 1968-01-18 AT AT03859/69A patent/AT279630B/en not_active IP Right Cessation
- 1968-01-18 SU SU1313323A patent/SU464112A3/en active
- 1968-01-18 AT AT385769A patent/AT279629B/en not_active IP Right Cessation
- 1968-01-18 AT AT53668A patent/AT279619B/en not_active IP Right Cessation
- 1968-01-18 YU YU0121/68A patent/YU32142B/en unknown
- 1968-01-18 GB GB2858/68A patent/GB1180164A/en not_active Expired
- 1968-05-30 ES ES354499A patent/ES354499A1/en not_active Expired
- 1968-05-30 ES ES354501A patent/ES354501A1/en not_active Expired
- 1968-05-30 ES ES354500A patent/ES354500A1/en not_active Expired
- 1968-05-30 ES ES354502A patent/ES354502A1/en not_active Expired
-
1969
- 1969-01-14 DK DK19669AA patent/DK118135B/en not_active IP Right Cessation
-
1971
- 1971-11-05 NO NO4096/71*[A patent/NO126527B/no unknown
-
1972
- 1972-10-30 YU YU2692/72A patent/YU33110B/en unknown
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