GB1496426A - 1,2-dihydro-4h-imidazo(1,2-alpha)(1,4)benzodiazepin-1-ones processes for their preparation and compositions incorporating them - Google Patents

1,2-dihydro-4h-imidazo(1,2-alpha)(1,4)benzodiazepin-1-ones processes for their preparation and compositions incorporating them

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Publication number
GB1496426A
GB1496426A GB6509/75A GB650975A GB1496426A GB 1496426 A GB1496426 A GB 1496426A GB 6509/75 A GB6509/75 A GB 6509/75A GB 650975 A GB650975 A GB 650975A GB 1496426 A GB1496426 A GB 1496426A
Authority
GB
United Kingdom
Prior art keywords
compounds
alkyl
hal
prepared
compound
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
Application number
GB6509/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roussel Laboratories Ltd
Original Assignee
Roussel Laboratories Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Roussel Laboratories Ltd filed Critical Roussel Laboratories Ltd
Priority to GB6509/75A priority Critical patent/GB1496426A/en
Priority to IL48888A priority patent/IL48888A/en
Priority to ZA760517A priority patent/ZA76517B/en
Priority to FR7603457A priority patent/FR2300569A1/en
Priority to CS76860A priority patent/CS193063B2/en
Priority to AR261199A priority patent/AR225721A1/en
Priority to SE7601592A priority patent/SE422686B/en
Priority to DE19762605652 priority patent/DE2605652A1/en
Priority to FI760347A priority patent/FI62090C/en
Priority to NZ179990A priority patent/NZ179990A/en
Priority to CH180876A priority patent/CH613706A5/en
Priority to BE164336A priority patent/BE838580A/en
Priority to NO760468A priority patent/NO146201C/en
Priority to LU74341A priority patent/LU74341A1/xx
Priority to HU76RO879A priority patent/HU173109B/en
Priority to IE298/76A priority patent/IE43791B1/en
Priority to DK58776AA priority patent/DK141250B/en
Priority to JP51014122A priority patent/JPS5914034B2/en
Priority to NLAANVRAGE7601492,A priority patent/NL171585C/en
Priority to PT64796A priority patent/PT64796B/en
Priority to PH18091A priority patent/PH14669A/en
Priority to YU345/76A priority patent/YU42471B/en
Priority to GR50055A priority patent/GR60028B/en
Priority to ES445188A priority patent/ES445188A1/en
Priority to EG77/76A priority patent/EG12462A/en
Priority to AU11137/76A priority patent/AU493448B2/en
Priority to AT107376A priority patent/AT351030B/en
Priority to MX176D priority patent/MX3327E/en
Priority to CA245,850A priority patent/CA1073454A/en
Priority to US05/658,301 priority patent/US4044142A/en
Priority to US05/791,845 priority patent/US4134976A/en
Publication of GB1496426A publication Critical patent/GB1496426A/en
Priority to PH21416A priority patent/PH15282A/en
Priority to CH1131378A priority patent/CH618171A5/en
Priority to DK524578A priority patent/DK141907B/en
Priority to PH22113A priority patent/PH16286A/en
Priority to HK473/79A priority patent/HK47379A/en
Priority to IT8047823A priority patent/IT8047823A0/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1496426 1,2 - Dehydro - 6 - phenyl - 4H- imidazo [1,2 - a] [1,4] benzodiazepin - 1 - ones ROUSSEL LABORATORIES Ltd 13 Feb 1976 [15 Feb 1975 4 Nov 1975] 6509/75 and 45800/75 Headings C2C and C2P Novel compounds (I) and their acid addition salts in which R<SP>1</SP> is H, Hal, NO 2 or CF 3 , R<SP>2</SP> is H or Hal, R<SP>3</SP> is H or Me and R<SP>4</SP> and R<SP>5</SP> are each H, C 1-5 alkyl, hydroxy C 1-5 alkyl or amino C 1-5 alkyl optionally mono- or di-C 1-5 alkylated or NR<SP>4</SP>R<SP>5</SP> represents an optionally substituted heterocyclic ring optionally containing a further hetero atom are prepared by reacting a compound V with dimethylformamide C 1-5 acetal or dimethylacetamide and, if desired, transaminating the resultant product with an amine R<SP>4</SP>R<SP>5</SP>NH (where R<SP>4</SP> and R<SP>5</SP> are other than both Me). Compounds I (NR<SP>4</SP>R<SP>5</SP> = piperazino) may be further reacted with a halide R<SP>6</SP>-Hal (where R<SP>6</SP> is cycloalkyl alkyl, alkenyl or dialkylphosphenylalkyl) to form compounds I (NR<SP>4</SP>R<SP>5</SP> = N-R<SP>6</SP>-piperazino). Compounds I are reacted with an acid to form the corresponding salt. Compounds V are prepared by cyclization of Compounds IV which are prepared by reacting a Compound II with a compound ROOC-CH 2 NH 2 , where R is an alkyl group. Compounds I have sedative, hypnotic, anxiolytic, tranquillizing, anticonvulsant and myorelaxant properties and form with a suitable vehicle a pharmaceutical composition which may be administered orally, parenterally or rectally.
GB6509/75A 1975-02-03 1975-02-15 1,2-dihydro-4h-imidazo(1,2-alpha)(1,4)benzodiazepin-1-ones processes for their preparation and compositions incorporating them Expired GB1496426A (en)

Priority Applications (37)

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
IL48888A IL48888A (en) 1975-02-15 1976-01-21 2-aminomethylene-1,2-dihydro-6-phenyl-1h-imidazo(1,2-a)(1,4) benzodiazepin-1-ones, process for their preparation andpharmaceutical compositions incorporating them
ZA760517A ZA76517B (en) 1975-02-15 1976-01-29 Imidozolobenzodiazepines processes for their preparation and compositions incorporating them
FR7603457A FR2300569A1 (en) 1975-02-15 1976-02-09 CNS-active imidazolobenzodiazepines - e.g. 8-chloro-1,2-dihydro-2-(N-methyl-piperazin-1-yl)methylene-6-pheny- l-1H, 4H-imidazo(1,2-a) (1,4)benzodiazepine-1-one
CS76860A CS193063B2 (en) 1975-02-15 1976-02-10 Process for preparing 1,2-dihydro-6-phenyl-1h,4h-imidazo-/1,2-a//1,4/benzodiazepin-1-ones
AR261199A AR225721A1 (en) 1975-02-15 1976-02-10 PROCEDURE FOR THE PREPARATION OF 1,2-DIHYDRO-6-PHENYL-1H, 4H-IMIDAZO (1,2-A) (1,4) -BENZODIAZEPIN-1-ONAS AND INTERMEDIARIES FOR YOUR EXCLUSIVE USE IN SUCH PROCEDURE
SE7601592A SE422686B (en) 1975-02-15 1976-02-12 ANALOGY PROCEDURE FOR PREPARATION OF 1,2-DIHYDRO-6-PHENYL-1H, 4H-IMIDAZO / 1,2-A) - (1,4) BENZODIAZEPIN-1-ONER
DE19762605652 DE2605652A1 (en) 1975-02-15 1976-02-12 IMIDAZOLOBENZODIAZEPINE, PROCEDURE FOR THEIR MANUFACTURING AND COMPOSITIONS CONTAINING THESE COMPOUNDS
FI760347A FI62090C (en) 1975-02-15 1976-02-12 PROCEDURE FOR THE FRAMSTATION OF 1,2-DIHYDRO-6-PHENYL-1H-4H-IMIDAZO (1,2-A) (1,4) BENZODIAZEPIN-1-ONER WITH A NETWORK OF NERVOUS SYSTEM
NZ179990A NZ179990A (en) 1975-02-15 1976-02-12 2-aminomethylene-1,2-dihydor-4h-imidazo (1,2-a) (1,4)-benzodiazepin-1-ones
PT64796A PT64796B (en) 1975-02-15 1976-02-13 PROCESS FOR THE PREPARATION OF IMIDAZOLE-BENZO-DIAZEPINES
BE164336A BE838580A (en) 1975-02-15 1976-02-13 NEW IMIDAZOLOBENZODIAZEPINES AND THEIR ADDITIONAL SALTS WITH ACIDS, METHOD OF PREPARATION AND PHARMACEUTICAL COMPOSITIONS
NO760468A NO146201C (en) 1975-02-15 1976-02-13 ANALOGUE PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE IMIDAZOLE BENZODIAZEPINES
LU74341A LU74341A1 (en) 1975-02-15 1976-02-13
HU76RO879A HU173109B (en) 1975-02-15 1976-02-13 Process for producing imidazolobenzodiazepine derivatives
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
DK58776AA DK141250B (en) 1975-02-15 1976-02-13 Analogous process for the preparation of 1,2-dihydro-6-phenyl-1H, 4H-imidazo (1,2-a) (1,4) benzodiazepin-1-ones.
JP51014122A JPS5914034B2 (en) 1975-02-15 1976-02-13 Imidazolobenzodiazepines, methods for producing these compounds, and compositions containing these compounds
NLAANVRAGE7601492,A NL171585C (en) 1975-02-15 1976-02-13 METHOD FOR THE PREPARATION OF PHARMACEUTICAL PREPARATIONS WITH ACTION ON THE CENTRAL NERVOUS SYSTEM BASED ON 6-PHENYL-1-OXOIMIDAZO-Ÿ1,2-AŸBENZOŸPHŸ-1,4-DIAZEPINES AND METHOD FOR THE PREPARATION OF THESE COMPOUNDS.
CH180876A CH613706A5 (en) 1975-02-15 1976-02-13 Process for the preparation of new imidazolobenzodiazepines and of their salts
PH18091A PH14669A (en) 1975-02-15 1976-02-13 1,2-dihydro-6-phenyl-1h,4h-imidazobenzodiazepin-1-one,composition and method of use thereof
YU345/76A YU42471B (en) 1975-02-15 1976-02-13 Process for obtaining 1,2-dihydro-6-phenyl-1h,4h-imidazo/1,2a//1,4/-benzodiazepin-1-ones
GR50055A GR60028B (en) 1975-02-15 1976-02-14 Process for the preparation of imidazolo benzodiazepines
ES445188A 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)
EG77/76A EG12462A (en) 1975-02-15 1976-02-14 Process for preparing imidazolobenzodiazepines
AU11137/76A AU493448B2 (en) 1976-02-16 Imidazolobenzodiazepines process for their preparation and compositions incorporating them
CA245,850A CA1073454A (en) 1975-02-15 1976-02-16 Imidazolobenzodiazepines, processes for their preparation and compositions incorporating them
AT107376A AT351030B (en) 1975-02-15 1976-02-16 PROCESS FOR THE PREPARATION OF NEW 1,2-DIHYDRO-6-PHENYL-1H, 4H-IMIDAZO (1,2A) (1,4) BENZODIAZEPIN-1-ONES AND THEIR ACID ADDITION SALTS
MX176D MX3327E (en) 1975-02-15 1976-02-16 PROCEDURE FOR THE PREPARATION OF IMIDAZOLOBENZODIAZEPINES
US05/658,301 US4044142A (en) 1975-02-03 1976-02-17 1,2-Dihydro-6-phenyl-1H,4H-imidazobenzodiazepin-1-ones
US05/791,845 US4134976A (en) 1975-02-15 1977-04-28 1,2-Dihydro-6-phenyl-1H,4H-imidazobenzodiazepin-1-ones
PH21416A PH15282A (en) 1975-02-15 1978-07-24 1,2-dihydro-6-phenyl-1h-imidazo-benzodiazepin-1-ones
CH1131378A CH618171A5 (en) 1975-02-15 1978-11-02 Process for the preparation of new imidazolobenzodiazepines and of their salts
DK524578A DK141907B (en) 1975-02-15 1978-11-24 Analogous process for the preparation of 1,2-dihydro-6-phenyl-1H, 4H-imidazo (1,2-a) (1,4) benzodiazepin-1-ones or acid addition salts thereof.
PH22113A PH16286A (en) 1975-02-15 1979-01-26 1,2-dihydro-6-phenyl-1h,4h-imidazo-benzodiazepin-1-ones
HK473/79A HK47379A (en) 1975-02-15 1979-07-12 1,2-dihydro-4h-imidazo(1,2-alpha)(1,4)benzodiazepin-1-ones, process for their preparation, and compositions incorporating them
IT8047823A IT8047823A0 (en) 1975-02-15 1980-02-06 IMIDAZOLE ORIGINAL BENZODIAZEPINES AND THEIR ACID ADDITION SALTS PRODUCTION PROCEDURE AND APPLICATION AS MEDICINES

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
GB1496426A true GB1496426A (en) 1977-12-30

Family

ID=9815820

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6509/75A Expired GB1496426A (en) 1975-02-03 1975-02-15 1,2-dihydro-4h-imidazo(1,2-alpha)(1,4)benzodiazepin-1-ones processes for their preparation and compositions incorporating them

Country Status (4)

Country Link
BE (1) BE838580A (en)
CS (1) CS193063B2 (en)
GB (1) GB1496426A (en)
ZA (1) ZA76517B (en)

Also Published As

Publication number Publication date
CS193063B2 (en) 1979-09-17
ZA76517B (en) 1977-02-23
BE838580A (en) 1976-08-13

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Legal Events

Date Code Title Description
PS Patent sealed
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PE20 Patent expired after termination of 20 years

Effective date: 19960212