GB972961A - A process for the manufacture of benzodiazepine derivatives - Google Patents
A process for the manufacture of benzodiazepine derivativesInfo
- Publication number
- GB972961A GB972961A GB42399/60A GB4239960A GB972961A GB 972961 A GB972961 A GB 972961A GB 42399/60 A GB42399/60 A GB 42399/60A GB 4239960 A GB4239960 A GB 4239960A GB 972961 A GB972961 A GB 972961A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- substituent
- nitro
- halogeno
- groups
- 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
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/26—Preparation from compounds already containing the benzodiazepine skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Compounds of the general formula <FORM:0972961/C1/1> (wherein R represents an optional alkyl, alkenyl or aralkyl substituent, R1 represents an optional alkyl substituent, R2 represents an optional alkyl, alkoxy, trifluoromethyl or halogeno substituent, R3 represents an optional trifluoromethyl, alkyl, alkoxy, alkylthio, hydroxyalkylthio, halogeno, nitro, amino, alkylsulphinyl, alkylsulphonyl, hydroxy or acylamino substituent and R4, which can only be present when R3 is other than a trifluoromethyl substituent, represents an optional alkyl, alkoxy, alkylthio, hydroxy-alkylthio, halogeno, nitro, amino, alkylsulphinyl, alkylsulphonyl, hydroxy or acylamino substituent, and the broken lines denote the bonds to the optional substituents) are prepared by reacting a 2-aminobenzophenone betaoxime of the general formula <FORM:0972961/C1/2> (wherein R30 and R40 have any of the values accorded to R3 and R4 except amino) with an a -halogenoacyl halide of the general formula <FORM:0972961/C1/3> (wherein X and Y represent halogeno substituents) in the presence of more than one mol of an acid-binding agent and, in the case where R30 and R40 were absent in the starting material, subjecting the benzodiazepine formed to one or more of the steps nitration, reduction of the nitro group and acylation of the resulting amino group where it is desired to introduce a nitro, amino or acylamino group or, in the case where one or both or R30 and R40 were nitro groups in the starting material, subjecting the benzodiazepine formed to one or both of the steps of reduction of the nitro group or groups and acylation of the resulting amino group or groups where one or two amino or acylamino groups is or are required in the product. The reaction proceeds through an intermediate acyl amide which can be isolated when the reaction is carried out stepwise using one mol of the acidbinding agent in the initial step. The preferred acid-binding agent is sodium hydroxide. 2-Chloroacetamido -5- chlorobenzophenone betaoxime is prepared by condensing 2-amino-5-chlorobenzophenone betaoxime with chloroacetyl chloride in the presence of approximately 1 mol of sodium hydroxide. Specification 972,968 is referred to.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85856459A | 1959-12-10 | 1959-12-10 | |
| US260560A | 1960-01-15 | 1960-01-15 | |
| US2468660A | 1960-04-26 | 1960-04-26 | |
| US3873260A | 1960-06-27 | 1960-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB972961A true GB972961A (en) | 1964-10-21 |
Family
ID=27485190
Family Applications (13)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42400/60A Expired GB972962A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42405/60A Expired GB972967A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42404/60A Expired GB972966A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB20071/63A Expired GB972976A (en) | 1959-12-10 | 1960-12-09 | Novel trifluoromethyl-benzophenones and the preparation thereof |
| GB40979/62A Expired GB972973A (en) | 1959-12-10 | 1960-12-09 | Novel trifluoromethyl-benzophenones and the preparation thereof |
| GB40978/62A Expired GB972972A (en) | 1959-12-10 | 1960-12-09 | Novel 2-amino-benzophenones and the preparation thereof |
| GB42401/60A Expired GB972963A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42399/60A Expired GB972961A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42403/60A Expired GB972965A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42402/60A Expired GB972964A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42408/60A Expired GB972968A (en) | 1959-12-10 | 1960-12-09 | Benzodiazepine derivatives |
| GB29834/62A Expired GB972970A (en) | 1959-12-10 | 1961-01-11 | Novel quinazoline 3-oxides and a process for the manufacture thereof |
| GB1168/61A Expired GB972969A (en) | 1959-12-10 | 1961-01-11 | Benzodiazepine derivatives and a process for the manufacture of same |
Family Applications Before (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42400/60A Expired GB972962A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42405/60A Expired GB972967A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42404/60A Expired GB972966A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB20071/63A Expired GB972976A (en) | 1959-12-10 | 1960-12-09 | Novel trifluoromethyl-benzophenones and the preparation thereof |
| GB40979/62A Expired GB972973A (en) | 1959-12-10 | 1960-12-09 | Novel trifluoromethyl-benzophenones and the preparation thereof |
| GB40978/62A Expired GB972972A (en) | 1959-12-10 | 1960-12-09 | Novel 2-amino-benzophenones and the preparation thereof |
| GB42401/60A Expired GB972963A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42403/60A Expired GB972965A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42402/60A Expired GB972964A (en) | 1959-12-10 | 1960-12-09 | A process for the manufacture of benzodiazepine derivatives |
| GB42408/60A Expired GB972968A (en) | 1959-12-10 | 1960-12-09 | Benzodiazepine derivatives |
| GB29834/62A Expired GB972970A (en) | 1959-12-10 | 1961-01-11 | Novel quinazoline 3-oxides and a process for the manufacture thereof |
| GB1168/61A Expired GB972969A (en) | 1959-12-10 | 1961-01-11 | Benzodiazepine derivatives and a process for the manufacture of same |
Country Status (11)
| Country | Link |
|---|---|
| BE (4) | BE598008A (en) |
| BR (1) | BR6024755D0 (en) |
| CH (9) | CH418342A (en) |
| CY (1) | CY324A (en) |
| DE (5) | DE1288609B (en) |
| ES (2) | ES263123A1 (en) |
| GB (13) | GB972962A (en) |
| MY (1) | MY6500178A (en) |
| NL (2) | NL6412250A (en) |
| OA (7) | OA00816A (en) |
| SE (2) | SE310887B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1300114B (en) * | 1963-05-29 | 1969-07-31 | American Home Prod | Process for the preparation of 5-chloro-2- (2'-hydroxylamino-acetamido) -benzophenone |
| GB1333501A (en) * | 1971-03-05 | 1973-10-10 | Ravizza Spa | Process for the preparation of 7-chlorobenzodiazepine de rivatives |
| US4820834A (en) * | 1984-06-26 | 1989-04-11 | Merck & Co., Inc. | Benzodiazepine analogs |
| CA1332410C (en) * | 1984-06-26 | 1994-10-11 | Roger M. Freidinger | Benzodiazepine analogs |
| EP1392663A2 (en) | 2001-06-07 | 2004-03-03 | Neuro3D | Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses thereof |
| CA2485681C (en) * | 2002-05-24 | 2012-10-16 | Millennium Pharmaceuticals, Inc. | Ccr9 inhibitors and methods of use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2893992A (en) * | 1959-07-07 | I ii i i |
-
1960
- 1960-12-02 CH CH1349360A patent/CH418342A/en unknown
- 1960-12-02 CH CH1349160A patent/CH408029A/en unknown
- 1960-12-02 CH CH1349460A patent/CH414652A/en unknown
- 1960-12-02 CH CH1349560A patent/CH414653A/en unknown
- 1960-12-02 CH CH1349060A patent/CH411910A/en unknown
- 1960-12-02 CH CH1348960A patent/CH408940A/en unknown
- 1960-12-02 CH CH1230565A patent/CH408045A/en unknown
- 1960-12-02 CH CH1349260A patent/CH418341A/en unknown
- 1960-12-07 DE DEH41137A patent/DE1288609B/en active Pending
- 1960-12-07 BR BR124755/60A patent/BR6024755D0/en unknown
- 1960-12-07 DE DEH41139A patent/DE1288610B/en active Pending
- 1960-12-07 DE DEH41138A patent/DE1290143B/en active Pending
- 1960-12-09 BE BE598008A patent/BE598008A/en unknown
- 1960-12-09 ES ES0263123A patent/ES263123A1/en not_active Expired
- 1960-12-09 GB GB42400/60A patent/GB972962A/en not_active Expired
- 1960-12-09 BE BE598013A patent/BE598013A/en unknown
- 1960-12-09 BE BE598015A patent/BE598015A/en unknown
- 1960-12-09 GB GB42405/60A patent/GB972967A/en not_active Expired
- 1960-12-09 ES ES0263124A patent/ES263124A1/en not_active Expired
- 1960-12-09 GB GB42404/60A patent/GB972966A/en not_active Expired
- 1960-12-09 GB GB20071/63A patent/GB972976A/en not_active Expired
- 1960-12-09 GB GB40979/62A patent/GB972973A/en not_active Expired
- 1960-12-09 BE BE598012A patent/BE598012A/en unknown
- 1960-12-09 GB GB40978/62A patent/GB972972A/en not_active Expired
- 1960-12-09 GB GB42401/60A patent/GB972963A/en not_active Expired
- 1960-12-09 GB GB42399/60A patent/GB972961A/en not_active Expired
- 1960-12-09 GB GB42403/60A patent/GB972965A/en not_active Expired
- 1960-12-09 GB GB42402/60A patent/GB972964A/en not_active Expired
- 1960-12-09 GB GB42408/60A patent/GB972968A/en not_active Expired
- 1960-12-13 CH CH1389960A patent/CH396016A/en unknown
- 1960-12-19 DE DE19601445073 patent/DE1445073A1/en active Pending
-
1961
- 1961-01-11 GB GB29834/62A patent/GB972970A/en not_active Expired
- 1961-01-11 GB GB1168/61A patent/GB972969A/en not_active Expired
-
1964
- 1964-09-10 DE DE19641445908 patent/DE1445908A1/en active Pending
- 1964-10-21 NL NL6412250A patent/NL6412250A/xx unknown
- 1964-10-21 NL NL6412251A patent/NL6412251A/xx unknown
- 1964-12-16 OA OA50895A patent/OA00816A/en unknown
- 1964-12-16 OA OA50896A patent/OA00817A/en unknown
- 1964-12-26 OA OA51048A patent/OA00953A/en unknown
- 1964-12-26 OA OA51053A patent/OA00958A/en unknown
- 1964-12-26 OA OA51054A patent/OA00959A/en unknown
-
1965
- 1965-09-17 SE SE12149/65A patent/SE310887B/xx unknown
- 1965-11-03 CY CY32465A patent/CY324A/en unknown
- 1965-12-31 MY MY1965178A patent/MY6500178A/en unknown
-
1967
- 1967-03-30 OA OA52850A patent/OA02385A/en unknown
- 1967-03-30 OA OA52849A patent/OA02384A/en unknown
- 1967-11-15 SE SE1570567A patent/SE318283B/xx unknown
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