ES445188A1 - A procedure for the preparation of a 1,2-dihydro-6-phenyl-1H, 4h-imidazo (1, 2-a) (1, 4) -benzodiazepin-1-ona. (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure for the preparation of a 1,2-dihydro-6-phenyl-1H, 4h-imidazo (1, 2-a) (1, 4) -benzodiazepin-1-ona. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES445188A1 ES445188A1 ES445188A ES445188A ES445188A1 ES 445188 A1 ES445188 A1 ES 445188A1 ES 445188 A ES445188 A ES 445188A ES 445188 A ES445188 A ES 445188A ES 445188 A1 ES445188 A1 ES 445188A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- radical
- compound
- already indicated
- represent
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- -1 alcohol radical Chemical class 0.000 abstract 5
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- IBYCDDNFZLAIAO-UHFFFAOYSA-N 2,4-dihydroimidazo[1,2-a][1,4]benzodiazepin-1-one Chemical compound C1N=CC2=CC=CC=C2N2C(=O)CN=C21 IBYCDDNFZLAIAO-UHFFFAOYSA-N 0.000 abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
A procedure for the preparation of a 1,2-dihydro-6-phenyl-1H, 4H-imidazo [1,2-a] [1,4] -benzodiazepin-1-one of general formula: **(See formula)** wherein R1 represents a hydrogen atom, a halogen atom, a nitro radical or a trifluoromethyl radical; R2, which can be in any appropriate position on the phenyl ring, represents a hydrogen atom or a halogen atom; R3 represents a hydrogen atom or a methyl radical; and R4 and R5, which may be the same or different, each represent a hydrogen atom, an alcohol radical containing from 1 to 5 carbon atoms, a hydroxyalkyl radical containing from 1 to 5 carbon atoms, an aminoalcohyl radical or alcohol-aminoalcohyl (each containing the alcohol moiety of 1 to 5 carbon atoms), an aryl radical or a cycloalkoxy radical, or R4 and R5 together with the nitrogen atom represent a saturated, substituted or unsubstituted heterocycle containing optionally another heteroatom; and one of its acid addition salts, characterized in that a compound of the formula: **(See formula)** in which R1 and R2 have the meanings already indicated, it is reacted well with a dimethylformamide acetal of the formula: (AlK-O) 2 = CH - N = (CH3) 2 where AlK represents a lower alcohol radical containing from 1 to 5 carbon atoms, giving 8-R'-1,2-dihydro-2- (dimethylamino) methylene-6- (R2-phenyl) -1H, 4H -imidazo [1,2-a] [1,4] benzodiazepin-1-one of formula: **(See formula)** wherein R1 and R2 have the meanings already indicated and that, if desired, said compound of formula (Ia) is either salified or transaminated by reaction with a suitable amine of formula: **(See formula)** where R4 and R5 have the meanings already indicated, except that both do not represent a methyl radical, giving the desired compound of formula: **(See formula)** wherein R1, R2, R4 and R5 have the meanings already indicated, except that R4 and R5 do not both represent a methyl radical, said compound being salified if desired, or said compound of formula (V) being reacted with an N- dimethyl acetamide of formula: **(See formula)** giving the corresponding compound of formula: **(See formula)** wherein R1 and R2 have the meanings already indicated and that, if desired, said compound of formula (Ib) is either salified or transaminated by reaction with a suitable amine of formula: **(See formula)** where R4 and R5 have the meanings already indicated, except that both do not represent a methyl radical, giving the desired compound of formula: **(See formula)** wherein R1, R2, R4 and R5 have the meanings already indicated, except that R4 and R5 do not both represent a methyl radical, said compound being salified, if desired. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6509/75A GB1496426A (en) | 1975-02-15 | 1975-02-15 | 1,2-dihydro-4h-imidazo(1,2-alpha)(1,4)benzodiazepin-1-ones processes for their preparation and compositions incorporating them |
| GB4580075 | 1975-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES445188A1 true ES445188A1 (en) | 1977-09-16 |
Family
ID=26240753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES445188A Expired ES445188A1 (en) | 1975-02-15 | 1976-02-14 | A procedure for the preparation of a 1,2-dihydro-6-phenyl-1H, 4h-imidazo (1, 2-a) (1, 4) -benzodiazepin-1-ona. (Machine-translation by Google Translate, not legally binding) |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5914034B2 (en) |
| AR (1) | AR225721A1 (en) |
| AT (1) | AT351030B (en) |
| CA (1) | CA1073454A (en) |
| CH (2) | CH613706A5 (en) |
| DE (1) | DE2605652A1 (en) |
| DK (1) | DK141250B (en) |
| EG (1) | EG12462A (en) |
| ES (1) | ES445188A1 (en) |
| FI (1) | FI62090C (en) |
| FR (1) | FR2300569A1 (en) |
| GR (1) | GR60028B (en) |
| HK (1) | HK47379A (en) |
| HU (1) | HU173109B (en) |
| IE (1) | IE43791B1 (en) |
| IL (1) | IL48888A (en) |
| IT (1) | IT8047823A0 (en) |
| LU (1) | LU74341A1 (en) |
| MX (1) | MX3327E (en) |
| NL (1) | NL171585C (en) |
| NO (1) | NO146201C (en) |
| NZ (1) | NZ179990A (en) |
| PH (3) | PH14669A (en) |
| PT (1) | PT64796B (en) |
| SE (1) | SE422686B (en) |
| YU (1) | YU42471B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2479818A1 (en) * | 1980-04-03 | 1981-10-09 | Roussel Uclaf | 2-Substd. phenyl 7-nitro 3H 1,4-benzodiazepinyl aminoacid derivs. - are anxiolytics, tranquillisers, sedatives and anticonvulsants, prepd. by reacting aminoacid or peptide with benzodiazepin-2-thione |
| FR2502621B1 (en) * | 1981-03-27 | 1983-10-28 | Roussel Uclaf |
-
1976
- 1976-01-21 IL IL48888A patent/IL48888A/en unknown
- 1976-02-09 FR FR7603457A patent/FR2300569A1/en active Granted
- 1976-02-10 AR AR261199A patent/AR225721A1/en active
- 1976-02-12 DE DE19762605652 patent/DE2605652A1/en active Granted
- 1976-02-12 SE SE7601592A patent/SE422686B/en not_active IP Right Cessation
- 1976-02-12 FI FI760347A patent/FI62090C/en not_active IP Right Cessation
- 1976-02-12 NZ NZ179990A patent/NZ179990A/en unknown
- 1976-02-13 PT PT64796A patent/PT64796B/en unknown
- 1976-02-13 YU YU345/76A patent/YU42471B/en unknown
- 1976-02-13 JP JP51014122A patent/JPS5914034B2/en not_active Expired
- 1976-02-13 DK DK58776AA patent/DK141250B/en not_active IP Right Cessation
- 1976-02-13 NO NO760468A patent/NO146201C/en unknown
- 1976-02-13 NL NLAANVRAGE7601492,A patent/NL171585C/en not_active IP Right Cessation
- 1976-02-13 HU HU76RO879A patent/HU173109B/en unknown
- 1976-02-13 PH PH18091A patent/PH14669A/en unknown
- 1976-02-13 IE IE298/76A patent/IE43791B1/en not_active IP Right Cessation
- 1976-02-13 CH CH180876A patent/CH613706A5/en not_active IP Right Cessation
- 1976-02-13 LU LU74341A patent/LU74341A1/xx unknown
- 1976-02-14 EG EG77/76A patent/EG12462A/en active
- 1976-02-14 ES ES445188A patent/ES445188A1/en not_active Expired
- 1976-02-14 GR GR50055A patent/GR60028B/en unknown
- 1976-02-16 MX MX176D patent/MX3327E/en unknown
- 1976-02-16 CA CA245,850A patent/CA1073454A/en not_active Expired
- 1976-02-16 AT AT107376A patent/AT351030B/en not_active IP Right Cessation
-
1978
- 1978-07-24 PH PH21416A patent/PH15282A/en unknown
- 1978-11-02 CH CH1131378A patent/CH618171A5/en not_active IP Right Cessation
-
1979
- 1979-01-26 PH PH22113A patent/PH16286A/en unknown
- 1979-07-12 HK HK473/79A patent/HK47379A/en unknown
-
1980
- 1980-02-06 IT IT8047823A patent/IT8047823A0/en unknown
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