GB1355170A - Benzodiazepine derivatives and a process for the manufacture thereof - Google Patents

Benzodiazepine derivatives and a process for the manufacture thereof

Info

Publication number
GB1355170A
GB1355170A GB2235872A GB1355170DA GB1355170A GB 1355170 A GB1355170 A GB 1355170A GB 2235872 A GB2235872 A GB 2235872A GB 1355170D A GB1355170D A GB 1355170DA GB 1355170 A GB1355170 A GB 1355170A
Authority
GB
United Kingdom
Prior art keywords
ketone
chloro
thiazolyl
nitrophenyl
methyl
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
GB2235872A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1355170A publication Critical patent/GB1355170A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1355170 Benzodiazepines F HOFFMANNLA ROCHE & CO AG 12 May 1972 [13 May 1971] 22368/72 Heading C2C Compounds of the general Formula (I) (B = CO, CH 2 ; R = H, halogen, CF 3 , NO 2 , amino, C 1-7 alkyl, 1-adamantylcarbonylamino, t-alkylcarbonylamino; R 1 = H, C 1-7 alkyl, hydroxyalkyl or aminoalkyl, C 2-7 alkenyl or alkynyl, cycloalkyl-(C 1-7 alkyl), C 1-7 alkylamino- (C 1-7 alkyl), di-(C 1-7 alkyl)amino-C 1-7 alkyl; R 2 = thiazolyl, isothiazolyl, pyrazolyl, 1-(C 1-7 alkyl)pyrazolyl, imidazolyl, 1-(C 1-7 alkyl)imidazolyl; R 3,4 = H or R 3+4 = C-N bond; R 5 =H, OH; provided that (i) when B = CO, R 3+4 = C-N bond, (ii) when B = CH 2 , R = halogen, NO 2 , amino, 1-adamantylcarbonylamino, talkylcarbonylamino, (iii) when B = CO, R 1 =H and R 2 = thiazolyl, R = amino, 1-adamantylcarbonylamino, t-alkylcarbonylamino and (iv) when R 5 = OH, B = CO and R 1 = C 1-7 alkyl) and their acid addition salts are prepared by standard methods, e.g. cyclizing an aminoacetamidophenyl ketone or reacting a 2-halo-5- nitrophenyl ketone with ethylene diamine or a derivative thereof, optionally followed by introduction of a 1-substituent, reduction of NO 2 to NH 3 and replacement of the latter by halogen and/or reduction of a 4,5-double bond. The preparation of α-(1-methyl-5-pyrazolyl)-5- chloro-2-nitrobenzyl alcohol, 5-chloro-2-nitrophenyl 1-methyl-5-pyrazolyl ketone, 2-amino-5- chlorophenyl 1-methyl-5-pyrazolyl ketone, 2-(2- bromoacetamido)-5-chlorophenyl 1-methyl-5-pyrazolyl ketone, α-(o-nitrophenyl)-2-thiazolylmethanol, o-nitrophenyl 2-thiazolyl ketone, o-aminophenyl 2-thiazolyl ketone, 2-bromoacetamidophenyl 2-thiazolyl ketone, 5-(2-thiazolyl)-1,3-dihydro-2H- 1,4-benzodiazepin-2-one, α-(2-thiazolyl)-2-chloro- 5-nitrobenzyl alcohol, 2-chloro-5-nitrophenyl 2- thiazolyl ketone, α-(1-methyl-5-pyrazolyl)-2-chloro- 5-nitrobenzyl alcohol, 2-chloro-5-nitrophenyl 1- methyl-5-pyrazolyl ketone, α-(1-methyl-2-imidazolyl)-5-chloro-2-nitrobenzyl alcohol, 5-chloro-2- nitrophenyl 1-methyl-2-imidazolyl ketone, 2-amino 5-chlorophenyl 1-methyl-2-imidazolyl ketone, 2-(2- bromoacetamido)-5-chlorophenyl 1-methyl-2-imidazolyl ketone, α-(1-methyl-2-imidazolyl)-2-chloro- 5-nitrobenzyl alcohol, 2-chloro-5-nitrophenyl 1- methyl-2-imidazolyl ketone, α-(5-chloro-2-nitrophenyl)-2-thiazolylmethanol, 5-chloro-2-nitrophenyl 2-thiazolyl ketone, 2-amino-5-chlorophenyl 2- thiazolyl ketone, 2-(2-bromoacetamido)-5-chlorophenyl 2-thiazolyl ketone, 7-chloro-5-(2-thiazolyl)- 1,3-dihydro-2H-1,4-benzodiazepin-2-one, α-(5- isothiazolyl)-5-chloro-2-nitrobenzyl alcohol, 5-chloro-2-nitrophenyl 5-isothiazolyl ketone, α-(5-isothiazolyl)-2-chloro-5-nitrobenzyl alcohol, 2-chloro- 5-nitrophenyl 5-isothiazolyl ketone, 2-amino-5- iodophenyl 2-thiazolyl ketone, 2-(2-bromoacetamido)-5-iodophenyl 2-thiazolyl ketone and 7-iodo-5- (2-thiazolyl)-1,3-dihydro-2H-1,4-benzodiazepin-2- one is described. The compounds (I) and their salts are anticonvulsants, muscle relaxants and sedatives, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.
GB2235872A 1971-05-13 1972-05-12 Benzodiazepine derivatives and a process for the manufacture thereof Expired GB1355170A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US14327671A 1971-05-13 1971-05-13

Publications (1)

Publication Number Publication Date
GB1355170A true GB1355170A (en) 1974-06-05

Family

ID=22503358

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2235872A Expired GB1355170A (en) 1971-05-13 1972-05-12 Benzodiazepine derivatives and a process for the manufacture thereof

Country Status (8)

Country Link
AU (1) AU4223272A (en)
BE (1) BE783475A (en)
DE (1) DE2223648A1 (en)
FR (1) FR2137839B1 (en)
GB (1) GB1355170A (en)
IL (1) IL39413A0 (en)
NL (1) NL7206427A (en)
ZA (1) ZA723228B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4208327A (en) * 1979-04-03 1980-06-17 G. D. Searle & Co. 5-Aryl-1-(2-oxazolin-2-yl)-1H-1,4-benzodiazepines and related compounds
EP0064820A1 (en) * 1981-04-22 1982-11-17 Farmos-Yhtyma Oy Substituted imidazole and imidazoline derivatives and their preparation and use

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2613720B1 (en) * 1987-04-10 1990-01-19 Esteve Labor Dr ARYL-HETEROARYL CARBINOL DERIVATIVES WITH ANALGESIC ACTIVITY
EP0475231A1 (en) * 1990-09-10 1992-03-18 F. Hoffmann-La Roche Ag Benzodiazepines
GB9116113D0 (en) * 1991-07-25 1991-09-11 Merck Sharp & Dohme Therapeutic agents

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4208327A (en) * 1979-04-03 1980-06-17 G. D. Searle & Co. 5-Aryl-1-(2-oxazolin-2-yl)-1H-1,4-benzodiazepines and related compounds
EP0064820A1 (en) * 1981-04-22 1982-11-17 Farmos-Yhtyma Oy Substituted imidazole and imidazoline derivatives and their preparation and use

Also Published As

Publication number Publication date
DE2223648A1 (en) 1972-11-16
FR2137839A1 (en) 1972-12-29
NL7206427A (en) 1972-11-15
BE783475A (en) 1972-11-16
IL39413A0 (en) 1972-07-26
AU4223272A (en) 1973-11-15
ZA723228B (en) 1973-02-28
FR2137839B1 (en) 1975-03-14

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees