IE43791L - Imidazolo-benzodiazepines - Google Patents
Imidazolo-benzodiazepinesInfo
- Publication number
- IE43791L IE43791L IE760298A IE29876A IE43791L IE 43791 L IE43791 L IE 43791L IE 760298 A IE760298 A IE 760298A IE 29876 A IE29876 A IE 29876A IE 43791 L IE43791 L IE 43791L
- Authority
- IE
- Ireland
- Prior art keywords
- radical
- carbon atoms
- piperazin
- phenyl
- alkyl
- Prior art date
Links
- KLNFAMGHSZQYHR-UHFFFAOYSA-N imidazo[4,5-i][1,2]benzodiazepine Chemical class C1=CC=NN=C2C3=NC=NC3=CC=C21 KLNFAMGHSZQYHR-UHFFFAOYSA-N 0.000 title 1
- -1 alkyl radical Chemical class 0.000 abstract 24
- 125000004432 carbon atom Chemical group C* 0.000 abstract 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 4
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 2
- 230000002082 anti-convulsion Effects 0.000 abstract 2
- 239000002249 anxiolytic agent Substances 0.000 abstract 2
- 230000000949 anxiolytic effect Effects 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 abstract 2
- 230000000147 hypnotic effect Effects 0.000 abstract 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 2
- 230000001670 myorelaxant effect Effects 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000000932 sedative agent Substances 0.000 abstract 2
- 230000001624 sedative effect Effects 0.000 abstract 2
- 230000002936 tranquilizing effect Effects 0.000 abstract 2
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)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1,2-Dihydro-6-phenyl-1H,4H-imidazo1,2a!1,4!benzodia-zepin-1-ones having the general formula: (I) wherein R1 represents a hydrogen atom, a halogen atom, a nitro radical or a trifluoromethyl radical; R2, which may be at any position in the phenyl ring, represents a hydrogen or halogen atom; R3 represents a hydrogen atom or a methyl radical; and R4 and R5, which are the same or different, each represents a hydrogen atom, an alkyl radical containing from 1 to 5 carbon atoms, a hydroxyalkyl radical containing from 1 to 5 carbon atoms, an aminoalkyl or alkylaminoalkyl radical in which the alkyl moieties each contains from 1 to 5 carbon atoms, a phenyl radical, or a cycloalkyl radical containing from 3 to 8 carbon atoms, or R4 and R5 represent together with the nitrogen atom to which they are bound a heterocyclic radical selected from the group consisting of pyrrolidinyl, piperidino, morpholino, thiomorpholino, piperazin-1-yl, 4-alkyl-piperazin-1-yl, 4-hydroxyalkyl-piperazin-1-yl, 4-phenyl-piperazin-1-yl, 4-(1'-phenyl-5'-imidazolyl-4'-one) piperazin-1-yl and R piperazin-1-yl radicals, in which R6 represents a cycloalkylalkyl radical containing from 3 to 8 carbon atoms, an alkenyl radical containing from 2 to 5 carbon atoms or a 4-dialkylphosphinyl alkyl radical, the alkyl moieties containing from 1 to 5 carbon atoms, and their pharmaceutically acceptable acid addition salts. These compounds have sedative, hypnotic, anxiolytic, tranquilizing, anticonvulsive and myorelaxant properties.
1,2-Dihydro-6-phenyl-1H,4H-imidazo¢1,2a!¢1,4!benzodia-zepin-1-ones having the general formula: (I) wherein R1 represents a hydrogen atom, a halogen atom, a nitro radical or a trifluoromethyl radical; R2, which may be at any position in the phenyl ring, represents a hydrogen or halogen atom; R3 represents a hydrogen atom or a methyl radical; and R4 and R5, which are the same or different, each represents a hydrogen atom, an alkyl radical containing from 1 to 5 carbon atoms, a hydroxyalkyl radical containing from 1 to 5 carbon atoms, an aminoalkyl or alkylaminoalkyl radical in which the alkyl moieties each contains from 1 to 5 carbon atoms, a phenyl radical, or a cycloalkyl radical containing from 3 to 8 carbon atoms, or R4 and R5 represent together with the nitrogen atom to which they are bound a heterocyclic radical selected from the group consisting of pyrrolidinyl, piperidino, morpholino, thiomorpholino, piperazin-1-yl, 4-alkyl-piperazin-1-yl, 4-hydroxyalkyl-piperazin-1-yl, 4-phenyl-piperazin-1-yl, 4-(1'-phenyl-5'-imidazolyl-4'-one) piperazin-1-yl and R piperazin-1-yl radicals, in which R6 represents a cycloalkylalkyl radical containing from 3 to 8 carbon atoms, an alkenyl radical containing from 2 to 5 carbon atoms or a 4-dialkylphosphinyl alkyl radical, the alkyl moieties containing from 1 to 5 carbon atoms, and their pharmaceutically acceptable acid addition salts. These compounds have sedative, hypnotic, anxiolytic, tranquilizing, anticonvulsive and myorelaxant properties.
[CA1073454A]
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE43791L true IE43791L (en) | 1976-08-15 |
| IE43791B1 IE43791B1 (en) | 1981-06-03 |
Family
ID=26240753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE298/76A IE43791B1 (en) | 1975-02-15 | 1976-02-13 | 1,2-dihydro-4h-imidazo/1,2-a/ /1,4/benzodiazepin-1-ones,prcess for their preparation,and compositions incorporating them |
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 NZ NZ179990A patent/NZ179990A/en unknown
- 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
- 1976-02-13 NO NO760468A patent/NO146201C/en unknown
- 1976-02-13 HU HU76RO879A patent/HU173109B/en unknown
- 1976-02-13 LU LU74341A patent/LU74341A1/xx unknown
- 1976-02-13 CH CH180876A patent/CH613706A5/en not_active IP Right Cessation
- 1976-02-13 PT PT64796A patent/PT64796B/en unknown
- 1976-02-13 NL NLAANVRAGE7601492,A patent/NL171585C/en not_active IP Right Cessation
- 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 DK DK58776AA patent/DK141250B/en not_active IP Right Cessation
- 1976-02-13 JP JP51014122A patent/JPS5914034B2/en not_active Expired
- 1976-02-13 YU YU345/76A patent/YU42471B/en unknown
- 1976-02-14 EG EG77/76A patent/EG12462A/en active
- 1976-02-14 GR GR50055A patent/GR60028B/en unknown
- 1976-02-14 ES ES445188A patent/ES445188A1/en not_active Expired
- 1976-02-16 AT AT107376A patent/AT351030B/en not_active IP Right Cessation
- 1976-02-16 MX MX176D patent/MX3327E/en unknown
- 1976-02-16 CA CA245,850A patent/CA1073454A/en not_active Expired
-
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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |