FR2183716A1 - Substd-6-phenyl-4h-imidazo (1,2-a)-1,4-benzo diazepines - - tranquillisers anxiolytics,sedatives and muscle-relaxants - Google Patents

Substd-6-phenyl-4h-imidazo (1,2-a)-1,4-benzo diazepines - - tranquillisers anxiolytics,sedatives and muscle-relaxants

Info

Publication number
FR2183716A1
FR2183716A1 FR7314310A FR7314310A FR2183716A1 FR 2183716 A1 FR2183716 A1 FR 2183716A1 FR 7314310 A FR7314310 A FR 7314310A FR 7314310 A FR7314310 A FR 7314310A FR 2183716 A1 FR2183716 A1 FR 2183716A1
Authority
FR
France
Prior art keywords
cpds
phenyl
substd
opt
halo
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.)
Granted
Application number
FR7314310A
Other languages
French (fr)
Other versions
FR2183716B1 (en
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.)
CENTRE ETD IND PHARMA
Original Assignee
CENTRE ETD IND PHARMA
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 CENTRE ETD IND PHARMA filed Critical CENTRE ETD IND PHARMA
Publication of FR2183716A1 publication Critical patent/FR2183716A1/en
Application granted granted Critical
Publication of FR2183716B1 publication Critical patent/FR2183716B1/fr
Granted legal-status Critical Current

Links

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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Cpds. of formulae (I), (III), (IV) and (V) including their acid addition salts and N-oxides: where R1= H, hydroxy, lower alkyl, lower alkoxy, lower alkoxy-carbonyl or acyloxy; R2, R3 = same or different H, halo, lower alkyl, lower alkoxy, CF3, nitro, opt. mono- or di-lower alkyl substd. amino, lower alkanoylthio, lower alkylsulphonyl, lower alkylsulphinyl, carboxy, lower acyloxy-carbonyl, lower acyloxy, cyano or carbamyl; R4= phenyl (opt. subst. by one or more halo or lower alkyl groups), cyclohexyl (opt. substd. by one or more alkyl gps.) or cyclohexenyl; R5= H, methyl or hydroxy; R6= H or halo. Cpds. (III), (IV) and (V) may also exist in their tautomeric forms. Tranquillisers, anxiolytics, sedatives, and muscle relaxants with low-toxicity which do not produce secondary effects such as a somnolence or obnubilation. They may be administered orally, rectally or parenterally in unit doses of 2-50 mg. and daily doses of 2-500 mg. Cpds. III, IV and V as well as being active cpds. are useful intermediates. The residue was recrystallised from cyclohexane/benzene to yield 8-chloro-1-methyl-6-phenyl-4H-imidazo 1,i-a 1,4-benzodiazepine (45% yield) m.pt. 190-192 degrees C.
FR7314310A 1972-05-05 1973-04-19 Substd-6-phenyl-4h-imidazo (1,2-a)-1,4-benzo diazepines - - tranquillisers anxiolytics,sedatives and muscle-relaxants Granted FR2183716A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2114172 1972-05-05
CH581473A CH571001A5 (en) 1972-05-05 1973-04-24

Publications (2)

Publication Number Publication Date
FR2183716A1 true FR2183716A1 (en) 1973-12-21
FR2183716B1 FR2183716B1 (en) 1976-12-03

Family

ID=25698412

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7314310A Granted FR2183716A1 (en) 1972-05-05 1973-04-19 Substd-6-phenyl-4h-imidazo (1,2-a)-1,4-benzo diazepines - - tranquillisers anxiolytics,sedatives and muscle-relaxants

Country Status (6)

Country Link
JP (1) JPS4947391A (en)
BE (1) BE798677A (en)
CA (1) CA999860A (en)
CH (1) CH571001A5 (en)
DE (1) DE2321705A1 (en)
FR (1) FR2183716A1 (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2290905A1 (en) * 1974-11-15 1976-06-11 Upjohn Co NEW PHARMACEUTICAL FORMULATION CONTAINING A BENZODIAZEPINE
US4134976A (en) * 1975-02-15 1979-01-16 Roussel Uclaf 1,2-Dihydro-6-phenyl-1H,4H-imidazobenzodiazepin-1-ones
WO2000069836A1 (en) * 1999-05-14 2000-11-23 Glaxo Group Limited Short-acting benzodiazepines
US7160880B1 (en) 1999-05-14 2007-01-09 Cenes Limited Short-acting benzodiazepines
US10195210B2 (en) 2010-11-08 2019-02-05 Paion Uk Ltd. Dosing regimen for sedation with CNS 7056 (Remimazolam)
US10472365B2 (en) 2006-07-10 2019-11-12 Paion Uk Limited Short-acting benzodiazepine salts and their polymorphic forms
EP3730495A4 (en) * 2017-12-28 2021-03-03 Hangzhou Adamerck Pharmlabs Inc. Pyridyl imidazobenzodiazepine propionate compound and synthesis and use thereof

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA755418B (en) * 1974-09-11 1977-06-29 Hoffmann La Roche Diazepine derivatives
US3910946A (en) * 1974-09-12 1975-10-07 Upjohn Co 4H-Imidazo{8 1,2-a{9 {8 1,4{9 benzodiazepines
US4044142A (en) 1975-02-03 1977-08-23 Roussel Uclaf 1,2-Dihydro-6-phenyl-1H,4H-imidazobenzodiazepin-1-ones
SE422580B (en) * 1975-08-07 1982-03-15 Hoffmann La Roche ANALOGY PROCEDURE FOR PREPARING IMIDAZO (1,5-A) (1,4) DIAZEPINE COMPOUNDS
US4185102A (en) 1975-11-04 1980-01-22 Roussel Uclaf 1,2-Dihydro-6-phenyl-1H,4H-imidazobenzodiazepin-1-ones
JPS60202096A (en) * 1984-03-22 1985-10-12 日産自動車株式会社 Shifter for fork of forklift
DE3610848A1 (en) * 1986-04-01 1987-10-15 Boehringer Ingelheim Kg NEW 1,4-DIAZEPINE
YU136287A (en) * 1986-07-25 1990-06-30 Boehringer Kg Process for preparing new 1,4 benzodiazepines
EP0518484A3 (en) * 1991-05-14 1993-03-17 Merck & Co. Inc. 1,4-benzodiazepines condesed with 5- and 6-membered heterocyclic rings to treat anxiety, pain, pupil constriction, withdrawal-syndrome or oncologic disorders
EP0763537A3 (en) * 1993-05-14 1997-10-22 Genentech Inc Non-peptidyl Ras farnesyl transferase inhibitors

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2150732A1 (en) * 1971-08-04 1973-04-13 Upjohn Co

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2150732A1 (en) * 1971-08-04 1973-04-13 Upjohn Co

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2290905A1 (en) * 1974-11-15 1976-06-11 Upjohn Co NEW PHARMACEUTICAL FORMULATION CONTAINING A BENZODIAZEPINE
US4134976A (en) * 1975-02-15 1979-01-16 Roussel Uclaf 1,2-Dihydro-6-phenyl-1H,4H-imidazobenzodiazepin-1-ones
US7485635B2 (en) 1999-05-14 2009-02-03 Cenes Limited Short-acting benzodiazepines
US7160880B1 (en) 1999-05-14 2007-01-09 Cenes Limited Short-acting benzodiazepines
US7435730B2 (en) 1999-05-14 2008-10-14 Cenes Limited Short-acting benzodiazepines
US7473689B2 (en) 1999-05-14 2009-01-06 Cenes Limited Short-acting benzodiazepines
WO2000069836A1 (en) * 1999-05-14 2000-11-23 Glaxo Group Limited Short-acting benzodiazepines
US7528127B2 (en) 1999-05-14 2009-05-05 Cenes Limited Short-acting benzodiazepines
US10472365B2 (en) 2006-07-10 2019-11-12 Paion Uk Limited Short-acting benzodiazepine salts and their polymorphic forms
US10961250B2 (en) 2006-07-10 2021-03-30 Paion Uk Limited Short-acting benzodiazepine salts and their polymorphic forms
US10195210B2 (en) 2010-11-08 2019-02-05 Paion Uk Ltd. Dosing regimen for sedation with CNS 7056 (Remimazolam)
US10342800B2 (en) 2010-11-08 2019-07-09 Paion Uk Ltd. Dosing regimen for sedation with CNS 7056 (Remimazolam)
EP3730495A4 (en) * 2017-12-28 2021-03-03 Hangzhou Adamerck Pharmlabs Inc. Pyridyl imidazobenzodiazepine propionate compound and synthesis and use thereof
US11919905B2 (en) 2017-12-28 2024-03-05 Hangzhou Adamerck Pharmlabs, Inc. Substituted benzo[f]imidazo[1,2-a][1,4]diazepines as anesthetics

Also Published As

Publication number Publication date
CA999860A (en) 1976-11-16
FR2183716B1 (en) 1976-12-03
BE798677A (en) 1973-08-16
JPS4947391A (en) 1974-05-08
CH571001A5 (en) 1975-12-31
DE2321705A1 (en) 1973-11-15

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