GB1449861A - Benzodiazepine and benzodiazocine derivatives - Google Patents
Benzodiazepine and benzodiazocine derivativesInfo
- Publication number
- GB1449861A GB1449861A GB4838973A GB4838973A GB1449861A GB 1449861 A GB1449861 A GB 1449861A GB 4838973 A GB4838973 A GB 4838973A GB 4838973 A GB4838973 A GB 4838973A GB 1449861 A GB1449861 A GB 1449861A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- bromo
- prepared
- alkyl
- alkoxy
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1449861 Benzodiazepine and benzodiazocine derivatives E R SQUIBB & SONS Inc 17 Oct 1973 [24 Oct 1972 8 March 1973] 48389/73 Heading C2C Novel compounds of the Formula I wherein m is 1 or 2; R is the same or different and is hydrogen, F, Cl, or Br, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, alkylthio of from 1 to 4 carbon atoms, benzyl, phenethyl, phenyl, phenylthio, or mono-substituted phenyl wherein the substituent is F, Cl, Br, I, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, or trifluoromethyl; provided that when R is halogen, R is in the 3- and/or 5-positions with respect to the pyridyl nitrogen as the 1-position; R<SP>1</SP> is hydrogen, F, Cl, Br, I, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, alkylthio of from 1 to 4 carbon atoms, alkylsulphonyl wherein the alkyl radical has from 1 to 4 carbon atoms, phenyl, phenyloxy, sulphamoyl, dialkylamidosulphonyl wherein each alkyl radical has from 1 to 4 carbon atoms, trifluoromethyl, mono-substituted phenyl or mono-substituted phenyloxy wherein the substituent is F, Cl, Br or I, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms or trifluoromethyl, and n is 2 or 3 and pharmaceutically acceptable salts thereof may be prepared by cyclizing, by the action of base and a copper catalyst, a compound IV or V Compounds of the Formula IV are prepared by reacting a 2-amino pyridine with a 2-bromophenethylbromide or a 3-(2-bromophenyl)- propylbromide. Treatment of an amine IV with base yields the corresponding imine V. The intermediate 2-bromophenethylbromides and 3 - (2 - bromophenyl)propylbromides are prepared by bromination of the corresponding 2-bromophenethanol or 3-(2-bromophenyl)propanol. 2 - Bromophenethanol and 2 - bromo - 4- chlorophenethanol are prepared by treating the corresponding 2-bromobenzylbromide with sodium cyanide to yield the corresponding 2- bromophenylacetonitrile which on ethanolysis yields the ethyl 2-bromophenylacetate which in the case of 4-chloro compound is hydrolysed to 2-bromo-4-chlorophenylacetic acid and then in both cases reduced to the required corresponding ethanol. 2-Bromobenzylbromide is prepared by bromination of 2-bromobenzylalcohol. 3 - (2 - Bromo - 4 - methylthiophenyl) - 1- propanol is prepared by reducing 2-bromo-4- nitrobenzoic acid to 2-bromo-4-aminobenzoic acid followed by diazotization and treatment with sodium methylmercaptide to yield 2- bromo - 4 - methylthiobenzoic acid which is converted to its methyl ester and reduced to 2- bromo - 4 - methylthiobenzylalcohol which is brominated to 2 - bromo - 4 - methylthiobenzylbromide converted to its Grignard reagent and then treated with ethylene oxide to yield the required compound. Pharmaceutical compositions of the compounds I when administered orally or parenterally show muscle relaxant and stimulant activity.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US29998672A | 1972-10-24 | 1972-10-24 | |
US00339258A US3825549A (en) | 1972-10-24 | 1973-03-08 | Certain dihydropyrido(2,1-b)(1,3)benzodi-azepines and benzodiazocines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1449861A true GB1449861A (en) | 1976-09-15 |
Family
ID=26971513
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4838973A Expired GB1449861A (en) | 1972-10-24 | 1973-10-17 | Benzodiazepine and benzodiazocine derivatives |
Country Status (6)
Country | Link |
---|---|
US (1) | US3825549A (en) |
JP (1) | JPS4975595A (en) |
CA (1) | CA1016167A (en) |
DE (2) | DE2365309A1 (en) |
FR (1) | FR2203640B1 (en) |
GB (1) | GB1449861A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3150522A1 (en) * | 1981-09-24 | 1983-04-07 | A. H. Robins Co. Inc., 23220 Richmond, Va. | Phenyl-substituted pyrido[1,4]benzodiazepines, intermediates and processes for their preparation, and their use as antidepressive agents |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA86171B (en) * | 1985-01-16 | 1986-08-27 | Hoffmann La Roche | Polycyclic salts |
US4925970A (en) * | 1988-12-22 | 1990-05-15 | Brown Richard W | Process for producing cyclohexadiene thioether |
US4990648A (en) * | 1988-12-22 | 1991-02-05 | Ici Americas Inc. | Process for producing an alkylthiobenzoate |
-
1973
- 1973-03-08 US US00339258A patent/US3825549A/en not_active Expired - Lifetime
- 1973-10-09 CA CA182,816A patent/CA1016167A/en not_active Expired
- 1973-10-17 GB GB4838973A patent/GB1449861A/en not_active Expired
- 1973-10-22 DE DE2365309*A patent/DE2365309A1/en active Pending
- 1973-10-22 DE DE19732352918 patent/DE2352918A1/en active Pending
- 1973-10-24 FR FR7337914A patent/FR2203640B1/fr not_active Expired
- 1973-10-24 JP JP48119816A patent/JPS4975595A/ja active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3150522A1 (en) * | 1981-09-24 | 1983-04-07 | A. H. Robins Co. Inc., 23220 Richmond, Va. | Phenyl-substituted pyrido[1,4]benzodiazepines, intermediates and processes for their preparation, and their use as antidepressive agents |
Also Published As
Publication number | Publication date |
---|---|
FR2203640B1 (en) | 1978-07-28 |
DE2365309A1 (en) | 1974-05-30 |
FR2203640A1 (en) | 1974-05-17 |
CA1016167A (en) | 1977-08-23 |
DE2352918A1 (en) | 1974-05-02 |
JPS4975595A (en) | 1974-07-20 |
US3825549A (en) | 1974-07-23 |
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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 |