IE38091B1 - Process for the manufacture of benzodiazepine derivatives - Google Patents

Process for the manufacture of benzodiazepine derivatives

Info

Publication number
IE38091B1
IE38091B1 IE1409/73A IE140973A IE38091B1 IE 38091 B1 IE38091 B1 IE 38091B1 IE 1409/73 A IE1409/73 A IE 1409/73A IE 140973 A IE140973 A IE 140973A IE 38091 B1 IE38091 B1 IE 38091B1
Authority
IE
Ireland
Prior art keywords
ammonia
benzodiazepine derivatives
general formula
hexamethylenetetramine
aug
Prior art date
Application number
IE1409/73A
Other versions
IE38091L (en
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of IE38091L publication Critical patent/IE38091L/en
Publication of IE38091B1 publication Critical patent/IE38091B1/en

Links

Classifications

    • 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
    • C07D243/24—Oxygen atoms
    • 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
    • C07D243/24—Oxygen atoms
    • C07D243/28—Preparation including building-up the benzodiazepine skeleton from compounds containing no hetero rings
    • 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
    • C07D243/24—Oxygen atoms
    • C07D243/30—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1392681 Benzodiazepine derivatives F HOFFMANN-LA ROCHE & CO AG 20 Aug 1973 [21 Aug 1972 14 May 1973] 39218/73 Heading C2C Benzodiazepine derivatives of general formula where R 1 is a hydrogen or halogen atom or a nitro or trifluoromethyl group, R 2 is a hydrogen atom or a C 1 -C 5 alkyl group, and R 3 is a phenyl, o-halophenyl or 2-pyridyl group are prepared by reacting a compound of general formula where X is Cl, Br or I, with hexamethylenetetramine in an inert organic solvent and in the presence of ammonia, with the possible isolation of an intermediate of general formula The ammonia may be formed in situ from an ammonia-generating agent, e.g. ammonium carbonate, and the hexamethylenetetramine may also be formed in situ from formaldehyde and ammonia. [GB1392681A]
IE1409/73A 1972-08-21 1973-08-15 Process for the manufacture of benzodiazepine derivatives IE38091B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US28221772A 1972-08-21 1972-08-21
US35981473A 1973-05-14 1973-05-14

Publications (2)

Publication Number Publication Date
IE38091L IE38091L (en) 1974-02-21
IE38091B1 true IE38091B1 (en) 1977-12-21

Family

ID=26961312

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1409/73A IE38091B1 (en) 1972-08-21 1973-08-15 Process for the manufacture of benzodiazepine derivatives

Country Status (24)

Country Link
JP (1) JPS5911589B2 (en)
AR (1) AR198108A1 (en)
AT (1) AT341527B (en)
AU (1) AU472777B2 (en)
CA (1) CA1012535A (en)
CH (1) CH578544A5 (en)
DD (1) DD107040A5 (en)
DE (1) DE2340159A1 (en)
DK (1) DK155326C (en)
ES (1) ES418014A1 (en)
FI (1) FI57939C (en)
FR (1) FR2197003B1 (en)
GB (1) GB1392681A (en)
HU (1) HU170153B (en)
IE (1) IE38091B1 (en)
IL (1) IL42947A (en)
LU (1) LU68269A1 (en)
NL (1) NL179582C (en)
NO (1) NO139481C (en)
PH (1) PH13640A (en)
PL (1) PL99162B1 (en)
SE (1) SE408302B (en)
SU (1) SU550980A3 (en)
YU (1) YU219873A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5334792A (en) * 1976-09-13 1978-03-31 Scherico Ltd Production of 1*44 benzodiazepines and 1*44 benzodiazepinee22ones
CN113149915B (en) * 2021-03-01 2024-03-15 中国科学院成都有机化学有限公司 Method for synthesizing clonazepam compound
CN116023342B (en) * 2021-10-26 2024-06-25 江苏昱林生物科技有限公司 Preparation method of high-purity clonazepam

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1136709B (en) * 1959-12-10 1962-09-20 Hoffmann La Roche Process for the preparation of 2-oxo-1, 2-dihydro-1, 4-benzodiazepines
CH537393A (en) * 1969-10-16 1973-05-31 Hoffmann La Roche Process for the preparation of 1,4-benzodiazepine derivatives
BE785962A (en) * 1971-07-08 1973-01-08 Hoffmann La Roche PROCESS FOR THE PREPARATION OF BENZODIAZEPINE DERIVATIVES

Also Published As

Publication number Publication date
NO139481C (en) 1979-03-21
ATA720773A (en) 1977-06-15
JPS5911589B2 (en) 1984-03-16
LU68269A1 (en) 1975-05-21
DE2340159C2 (en) 1989-01-19
NO139481B (en) 1978-12-11
AR198108A1 (en) 1974-05-31
NL179582B (en) 1986-05-01
FI57939B (en) 1980-07-31
IL42947A0 (en) 1973-11-28
GB1392681A (en) 1975-04-30
DK155326B (en) 1989-03-28
ES418014A1 (en) 1976-03-16
JPS4956992A (en) 1974-06-03
FR2197003A1 (en) 1974-03-22
CA1012535A (en) 1977-06-21
SE408302B (en) 1979-06-05
FI57939C (en) 1980-11-10
HU170153B (en) 1977-04-28
PL99162B1 (en) 1978-06-30
AU5918073A (en) 1975-02-13
DD107040A5 (en) 1974-07-12
AT341527B (en) 1978-02-10
IL42947A (en) 1977-01-31
YU219873A (en) 1982-06-30
AU472777B2 (en) 1976-06-03
CH578544A5 (en) 1976-08-13
NL7311507A (en) 1974-02-25
DK155326C (en) 1989-08-14
SU550980A3 (en) 1977-03-15
DE2340159A1 (en) 1974-03-07
IE38091L (en) 1974-02-21
FR2197003B1 (en) 1978-01-13
NL179582C (en) 1986-10-01
PH13640A (en) 1980-08-18

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