ES422941A1 - 2-3-phthalimidomethyl-4h-1,2,4-triazol-4-yl-benzophenones and production of 6-benzodiazepines - Google Patents

2-3-phthalimidomethyl-4h-1,2,4-triazol-4-yl-benzophenones and production of 6-benzodiazepines

Info

Publication number
ES422941A1
ES422941A1 ES422941A ES422941A ES422941A1 ES 422941 A1 ES422941 A1 ES 422941A1 ES 422941 A ES422941 A ES 422941A ES 422941 A ES422941 A ES 422941A ES 422941 A1 ES422941 A1 ES 422941A1
Authority
ES
Spain
Prior art keywords
formula
group
alkyl
compound
production
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
ES422941A
Other languages
Spanish (es)
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of ES422941A1 publication Critical patent/ES422941A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Process for the production of a 6-phenyl-4H-s-triazole- [4,3, a] [1,4] zodiazepine, of the formula III **(See formula)** wherein R1 is selected from the group consisting of hydrogen, alkyl of 1 to 3 inclusive carbon atoms, phenyl, benzyl and COOR'in which R' is alkyl defined as above; and wherein R2, R3, R4 and R5 are selected from the group consisting of hydrogen, alkyl defined as above, halogen, nitro, cyano, trifluoromethyl and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl and alkanoylamino in which the carbonaceous group has from 1 to 3 carbon atoms inclusive, and dialkylamino in which alkyl is defined as above, characterized in that it consists of: treating a compound of formula I: wherein R1, R2, R3, R4 and R5 are defined as above, with methanesulfonyl chloride and a volatile tertiary amine selected from triethylamine, diethylmethylamine, dimethylethylamine and dipropylathylamine between -40º and 10ºC, to obtain the corresponding compound of formula II **(See formula)** where R1, R2, R3, R4, and R5 are defined as above and A is **(See formula)** and heating II with a compound selected from the group consisting of ammonia and hexamethylenetetramine in the presence of an alkali metal iodide to obtain the corresponding compound of formula III. (Machine-translation by Google Translate, not legally binding)
ES422941A 1973-02-14 1974-02-05 2-3-phthalimidomethyl-4h-1,2,4-triazol-4-yl-benzophenones and production of 6-benzodiazepines Expired ES422941A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US33237773A 1973-02-14 1973-02-14

Publications (1)

Publication Number Publication Date
ES422941A1 true ES422941A1 (en) 1976-09-16

Family

ID=23297958

Family Applications (2)

Application Number Title Priority Date Filing Date
ES422941A Expired ES422941A1 (en) 1973-02-14 1974-02-05 2-3-phthalimidomethyl-4h-1,2,4-triazol-4-yl-benzophenones and production of 6-benzodiazepines
ES445860A Expired ES445860A1 (en) 1973-02-14 1976-03-08 2-3-phthalimidomethyl-4h-1,2,4-triazol-4-yl-benzophenones and production of 6-benzodiazepines

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES445860A Expired ES445860A1 (en) 1973-02-14 1976-03-08 2-3-phthalimidomethyl-4h-1,2,4-triazol-4-yl-benzophenones and production of 6-benzodiazepines

Country Status (16)

Country Link
JP (1) JPS49110699A (en)
AU (1) AU471038B2 (en)
BE (1) BE811025A (en)
CA (1) CA999000A (en)
CH (2) CH587263A5 (en)
DE (1) DE2402363A1 (en)
DK (1) DK140803B (en)
ES (2) ES422941A1 (en)
FR (1) FR2217335B1 (en)
GB (3) GB1454684A (en)
HU (1) HU168136B (en)
IL (3) IL49503A (en)
NL (1) NL7400958A (en)
PH (2) PH10784A (en)
SE (2) SE423546B (en)
ZA (1) ZA74466B (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3709898A (en) * 1971-02-09 1973-01-09 Upjohn Co Process for the production of triazolobenzodiazepines and intermediates

Also Published As

Publication number Publication date
CA999000A (en) 1976-10-26
PH11789A (en) 1978-07-05
IL44068A0 (en) 1974-05-16
IL44068A (en) 1977-05-31
DE2402363A1 (en) 1974-08-22
NL7400958A (en) 1974-08-16
IL49503A0 (en) 1976-06-30
GB1454683A (en) 1976-11-03
DK140803B (en) 1979-11-19
SE435285B (en) 1984-09-17
AU471038B2 (en) 1976-04-08
JPS49110699A (en) 1974-10-22
BE811025A (en) 1974-08-14
AU6478674A (en) 1975-07-24
FR2217335A1 (en) 1974-09-06
SE423546B (en) 1982-05-10
PH10784A (en) 1977-09-06
HU168136B (en) 1976-02-28
CH586704A5 (en) 1977-04-15
ES445860A1 (en) 1977-05-01
ZA74466B (en) 1974-12-24
GB1454682A (en) 1976-11-03
FR2217335B1 (en) 1977-06-10
SE8107017L (en) 1981-11-25
GB1454684A (en) 1976-11-03
IL49503A (en) 1977-05-31
DK140803C (en) 1980-04-21
CH587263A5 (en) 1977-04-29

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