GB1423241A - Synthesis of anti-oximes - Google Patents

Synthesis of anti-oximes

Info

Publication number
GB1423241A
GB1423241A GB2480173A GB2480173A GB1423241A GB 1423241 A GB1423241 A GB 1423241A GB 2480173 A GB2480173 A GB 2480173A GB 2480173 A GB2480173 A GB 2480173A GB 1423241 A GB1423241 A GB 1423241A
Authority
GB
United Kingdom
Prior art keywords
isomer
formula
syn
oxime
alkyl
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
GB2480173A
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.)
Wyeth LLC
Original Assignee
American Home Products Corp
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
Priority claimed from US294724A external-priority patent/US3873604A/en
Application filed by American Home Products Corp filed Critical American Home Products Corp
Publication of GB1423241A publication Critical patent/GB1423241A/en
Expired legal-status Critical Current

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

Landscapes

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

Abstract

1423241 2 - Acylaminobenzophenone antioximes AMERICAN HOME PRODUCTS CORP 24 May 1973 [1 June 1972 3 Oct 1972] 24801/73 Heading C2C Novel compounds of Formula C in which R is H or C 1 -C 6 alkyl, each of R<SP>1</SP> and R<SP>2</SP> is C 1 -C 6 carboxylic acyl, and each of X and Y is H, halogen, CF 3 , NO 2 , CN, CH 3 S, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, are prepared by reacting a compound of Formula D with a compound of Formula E in which Z is Cl or Br. Compounds C are useful as intermediates in the production of pharmaceutically useful benzodiazepinones. 2,2 - Dihydroxyacetyl chloride, diactate is prepared by reacting glyoxylic acid monohydrate with acetic acid and then with thionyl chloride. Anti-oximes of Formula D are obtained by (a) contacting a mixture of the anti-oxime and its syn isomer in solution in an inert polar organic solvent with at least one metal ion selected from Zn II, Cu II, Ni II, Co III, Fe II, Mn II and Cr III, (b) isolating the thus formed o-aminobenzophenone anti-oxime metal salt chelate and (c) dissociating the metal salt chelate. The syn-isomer may be recovered from the solvent. Certain of the metal ions also induce isomerization of the syn-isomer to the anti-isomer thus increasing the yield of the desired anti-isomer.
GB2480173A 1972-06-01 1973-05-24 Synthesis of anti-oximes Expired GB1423241A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25866672A 1972-06-01 1972-06-01
US294724A US3873604A (en) 1972-10-03 1972-10-03 Synthesis of 1,4-benzodiazepin-2-ones

Publications (1)

Publication Number Publication Date
GB1423241A true GB1423241A (en) 1976-02-04

Family

ID=26946789

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2480173A Expired GB1423241A (en) 1972-06-01 1973-05-24 Synthesis of anti-oximes
GB1698175A Expired GB1423242A (en) 1972-06-01 1973-05-24 Synthesis of 1,4-benzodiazepin 2 ones

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1698175A Expired GB1423242A (en) 1972-06-01 1973-05-24 Synthesis of 1,4-benzodiazepin 2 ones

Country Status (5)

Country Link
JP (1) JPS4961187A (en)
CH (1) CH590852A5 (en)
DE (1) DE2327715A1 (en)
FR (1) FR2197878B1 (en)
GB (2) GB1423241A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4472435A (en) * 1980-07-31 1984-09-18 Hoffman-La Roche Inc. Benzophenone derivatives useful in treating heart failure

Also Published As

Publication number Publication date
JPS4961187A (en) 1974-06-13
CH590852A5 (en) 1977-08-31
DE2327715A1 (en) 1973-12-20
FR2197878B1 (en) 1977-04-29
FR2197878A1 (en) 1974-03-29
GB1423242A (en) 1976-02-04

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee