GB1088621A - Improvements in or relating to podophyllin derivatives - Google Patents

Improvements in or relating to podophyllin derivatives

Info

Publication number
GB1088621A
GB1088621A GB4969664A GB4969664A GB1088621A GB 1088621 A GB1088621 A GB 1088621A GB 4969664 A GB4969664 A GB 4969664A GB 4969664 A GB4969664 A GB 4969664A GB 1088621 A GB1088621 A GB 1088621A
Authority
GB
United Kingdom
Prior art keywords
formula
acid
demethoxy
hydrogen
compounds
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
GB4969664A
Inventor
Juerg Rutschmann
Emil Schreier
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.)
Sandoz AG
Original Assignee
Sandoz 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
Priority claimed from CH1522863A external-priority patent/CH437346A/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1088621A publication Critical patent/GB1088621A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings

Landscapes

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

Abstract

Novel compounds of the formula <FORM:1088621/C2/1> wherein either R1 represents a hydrogen atom and R2 with R3 represents a direct bond or R1 represents a hydrogen atom or a hydroxy or acetoxy radical and each of R2 and R3 represent a hydrogen atom, are prepared (a) in the case wherein R1 represents hydrogen and R2 with R3 represents a direct bond (31, 41, 51 -demethoxy-b -apopicropodophyllin) by splitting off two molecules of water from 31,41,51 -demethoxyisopodophyllinic acid of formula <FORM:1088621/C2/2> (b) in the case where R2 and R3 represent hydrogen and R1 represents a hydrogen atom or a hydroxy or acetoxy radical, by adding the elements of water to the 3,4-double bond of the novel compound 31,41,51 -demethoxy-a -apopicropodophyllin of the formula <FORM:1088621/C2/3> (obtainable by saponifying 31,41,51 -demethoxy-b -apopicropodophyllin of the formula <FORM:1088621/C2/4> and splitting off water under mild conditions from the resulting 31,41,51 -demethoxy-a -apopicropodophyllinic acid of the formula <FORM:1088621/C2/5> to form a mixture of 31, 41, 51 -demethoxypicropodophyllin and -epipicropodophyllin, i.e. compounds where R1 is hydroxy and, when required, separating the mixture and acetylating or hydrogenating the mixture or the separated compounds to form compounds where R1 is acetoxy and hydrogen respectively; or by splitting off a molecule of water under mild condition from 31,41,51 -demethoxyisopodophyllinic acid to form 31,41,51 -demethoxy-isopodo-phyllotoxin, i.e. a compound where R1 is hydroxy and, when required, acetylating or hydrogenating as before to form R1 acetoxy or hydrogen; or by catalytically hydrogenating 31,41,51 - demethoxy - isopodophyllinic acid and lactonizing the resulting novel 31,41,51 -demethoxy-4-desoxy-isopodophyllinic acid of the formula <FORM:1088621/C2/6> to form a compound wherein R1 is hydrogen. Pharmaceutical compositions for parenteral, enteral or intranasal administration contain compounds of the first formula above and are useful for slowing down or preventing cell division or multiplication. 31,41,51 - Demethoxy - isopodophyllinic acid of the second formula above is obtained by the condensation of a benzo-piperone of the formula <FORM:1088621/C2/7> with diethyl succinate and saponifying the intermediate semi-ester to form a mixture of benzhydrylidene succinic acids of the formula <FORM:1088621/C2/8> partially hydrogenating these acids to form a benzhydryl succinic acid of the formula <FORM:1088621/C2/9> converting this acid to the corresponding anhydride, subjecting the anhydride to an intramolecular Friedel-Craft reaction with subsequent esterification of the resulting naphthoic acid to form the corresponding ethyl ester of the formula <FORM:1088621/C2/100> treating this compound with ethyl formate and sodium, and reducing the resulting 3-hydroxymethylene-naphthoi ester of the formula <FORM:1088621/C2/111> with an alkali metal borohydride.
GB4969664A 1963-12-12 1964-12-07 Improvements in or relating to podophyllin derivatives Expired GB1088621A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1522863A CH437346A (en) 1963-12-12 1963-12-12 Process for the preparation of a new carbocyclic compound
CH1564063A CH445521A (en) 1963-12-12 1963-12-19 Process for the preparation of new carbocyclic compounds

Publications (1)

Publication Number Publication Date
GB1088621A true GB1088621A (en) 1967-10-25

Family

ID=25715960

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4969664A Expired GB1088621A (en) 1963-12-12 1964-12-07 Improvements in or relating to podophyllin derivatives

Country Status (1)

Country Link
GB (1) GB1088621A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4122092A (en) * 1977-08-25 1978-10-24 University Of Rochester Total synthesis of (±)-picropodophyllone and (±)-4'-demethylpicropodophyllone
US20150031759A1 (en) * 2008-02-09 2015-01-29 University Of Nebraska - Lincoln Analogues of (-)Picropodophyllin, Synthesis And Uses Thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4122092A (en) * 1977-08-25 1978-10-24 University Of Rochester Total synthesis of (±)-picropodophyllone and (±)-4'-demethylpicropodophyllone
US20150031759A1 (en) * 2008-02-09 2015-01-29 University Of Nebraska - Lincoln Analogues of (-)Picropodophyllin, Synthesis And Uses Thereof

Similar Documents

Publication Publication Date Title
GB1205050A (en) Process for preparing bicyclopentadecenones
GB1242194A (en) A new oestratriol and a process for its manufacture
GB1212090A (en) Aliphatic diol-diones
ES301833A1 (en) A procedure for the preparation of 19-alkil-steroids (Machine-translation by Google Translate, not legally binding)
GB1088621A (en) Improvements in or relating to podophyllin derivatives
GB1479362A (en) 3,17,18-trihydroxy-1,3,5(10)-oestratrienes and their derivatives
GB901293A (en) Improvements in or relating to steroids
GB1058543A (en) 16-methylene-steroids
GB1060793A (en) Improvements in or relating to steroids and the manufacture thereof
GB1355667A (en) Alpha-beta-unsaturated delta-lactones and process for the pre paration
ES421713A1 (en) Pregnane acid derivatives
GB1209398A (en) Oxygenated decalin derivatives
GB1110759A (en) Oestrogenically active steroids and a process for their manufacture
GB1074491A (en) Novel processes for preparing steroid compounds, the compounds when thus prepared, novel steroid compounds thereby prepared, and pharmaceutical compositions containing the novel compounds
GB1427253A (en) Antilipemic composition containing unsaponifiable matter of soybean oil
GB1053339A (en)
US3465009A (en) Novel intermediates in the preparation of 13 - polycarbonalkyl - 17alpha - hydroxy-18,19 - dinorpregn - 4 - en - 3,20 - diones and acylates thereof
ES421790A1 (en) Procedure for preparation of prostate acid derivatives. (Machine-translation by Google Translate, not legally binding)
INOUE et al. Studies on Monoterpene Glucosides and Related Natural Products. XV. Confirmation of the Absolute Configuration of Catalpol
GB987061A (en) Vitamin a compositions
GB1174385A (en) 0-Pyridyl-1,2,3,4-Tetrahydroisoquinoline Derivatives
GB1242372A (en) A new oestratriol and a process for its manufacture
GB1185381A (en) 05,16beta-Methylene Steroids of the 19-Nor-Androstane Series and Process for their Manufacture
ES330679A1 (en) Procedure for preparing physiologically active steroids. (Machine-translation by Google Translate, not legally binding)
ES369991A1 (en) Procedure to produce a composite of prostaglandinas. (Machine-translation by Google Translate, not legally binding)