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FR2365345A2 - (14)-Acyloxy-daunorubicin derivs. - with antitumour activity - Google Patents

(14)-Acyloxy-daunorubicin derivs. - with antitumour activity

Info

Publication number
FR2365345A2
FR2365345A2 FR7628977A FR7628977A FR2365345A2 FR 2365345 A2 FR2365345 A2 FR 2365345A2 FR 7628977 A FR7628977 A FR 7628977A FR 7628977 A FR7628977 A FR 7628977A FR 2365345 A2 FR2365345 A2 FR 2365345A2
Authority
FR
France
Prior art keywords
daunorubicin
derivs
mouse
acyloxy
doses
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.)
Granted
Application number
FR7628977A
Other languages
French (fr)
Other versions
FR2365345B2 (en
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.)
Rhone Poulenc Industries SA
Original Assignee
Rhone Poulenc Industries SA
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 Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA
Priority to FR7628977A priority Critical patent/FR2365345A2/en
Priority to NLAANVRAGE7612239,A priority patent/NL170737C/en
Priority to CA265,119A priority patent/CA1072954A/en
Priority to SU762418213A priority patent/SU659095A3/en
Priority to CS767234A priority patent/CS209876B2/en
Priority to PH19114A priority patent/PH13709A/en
Priority to IE248476A priority patent/IE44076B1/en
Priority to AU19506/76A priority patent/AU504388B2/en
Priority to NZ182591A priority patent/NZ182591A/en
Priority to JP13510676A priority patent/JPS5285161A/en
Priority to GB46807/76A priority patent/GB1525180A/en
Priority to IL50897A priority patent/IL50897A/en
Priority to NO763857A priority patent/NO143349C/en
Priority to CH1423376A priority patent/CH606081A5/xx
Priority to LU76176A priority patent/LU76176A1/xx
Priority to DK508776A priority patent/DK508776A/en
Priority to AR265428A priority patent/AR213419A1/en
Priority to HU76RO00000903A priority patent/HU172526B/en
Priority to SE7612613A priority patent/SE421212B/en
Priority to YU02778/76A priority patent/YU277876A/en
Priority to DE2651773A priority patent/DE2651773C3/en
Priority to AT842876A priority patent/AT347583B/en
Priority to FI763251A priority patent/FI62316C/en
Priority to ES453264A priority patent/ES453264A1/en
Priority to US05/849,761 priority patent/US4225589A/en
Publication of FR2365345A2 publication Critical patent/FR2365345A2/en
Application granted granted Critical
Publication of FR2365345B2 publication Critical patent/FR2365345B2/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
    • 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
    • C07D317/10—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 not condensed with other rings
    • C07D317/32—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 not condensed with other rings 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
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Daunorubicin derivs. of formula (I) and their acid-addn. salts are novel. In the formula X are O or S; when X are the same, R3 are 1-4C alkyl or phenyl opt. p-substd. by Me, MeO or MeS, or together form a 2-4c alkylene gp.; when, X are different, R3 together form 2-4C alkylene; R4 is H, 1-4C alkyl or phenyl; R2 is H or CF3CO. Cpds. (I) are antitumour agents with low toxicity (MTD=0.5-30 mg/kg, i.p., mouse). They are active against leukaemias (L 1210 and P 388) at doses of 0.25-20 mg/kg (i.p., mouse) and against mammary and pulmonary carcinoma at doses of 1-20 mg/kg (i.v., mouse). A typical cpd., 14-diethoxyacetoxy-daunorubicin hydrochloride, is prepd. from 14-bromodaunorubicin 13-dimetheylacetal hydrochloride and Na diethoxyacetate.
FR7628977A 1975-11-12 1976-09-27 (14)-Acyloxy-daunorubicin derivs. - with antitumour activity Granted FR2365345A2 (en)

Priority Applications (25)

Application Number Priority Date Filing Date Title
FR7628977A FR2365345A2 (en) 1976-09-27 1976-09-27 (14)-Acyloxy-daunorubicin derivs. - with antitumour activity
NLAANVRAGE7612239,A NL170737C (en) 1975-11-12 1976-11-04 PROCESS FOR PREPARING ESTERS OF ADRIAMYCIN AGAINST TUMORS, AND PREPARING MEDICINES WITH ANTI-TUMOR ACTIVITY.
CA265,119A CA1072954A (en) 1975-11-12 1976-11-08 Derivatives of daunorubicin; their preparation and compositions thereof
SU762418213A SU659095A3 (en) 1975-11-12 1976-11-09 Method of obtaining dahunorubicin derivatives or salts thereof
CS767234A CS209876B2 (en) 1975-11-12 1976-11-09 Method of preparation of the new daunorubicine derivatives
IE248476A IE44076B1 (en) 1975-11-12 1976-11-10 Daunorubicin derivatives
AU19506/76A AU504388B2 (en) 1975-11-12 1976-11-10 Daunorubicin derivatives
NZ182591A NZ182591A (en) 1975-11-12 1976-11-10 14-substituted-daunorubicins and pharmaceutical compositions
JP13510676A JPS5285161A (en) 1975-11-12 1976-11-10 Daunorbicine derivatives
GB46807/76A GB1525180A (en) 1975-11-12 1976-11-10 Daunorubicin derivatives
PH19114A PH13709A (en) 1975-11-12 1976-11-10 Daunorubicin derivatives and pharmaceutical compositions containing same
CH1423376A CH606081A5 (en) 1975-11-12 1976-11-11
IL50897A IL50897A (en) 1975-11-12 1976-11-11 Daunorubicin derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same
LU76176A LU76176A1 (en) 1975-11-12 1976-11-11
DK508776A DK508776A (en) 1975-11-12 1976-11-11 PROCEDURE FOR THE PREPARATION OF DAUNORUBICIN DERIVATIVES OR ACID ADDITIONAL SALTS THEREOF
AR265428A AR213419A1 (en) 1975-11-12 1976-11-11 PROCEDURE FOR PREPARING NEW DAUNORUBICIN DERIVATIVES
HU76RO00000903A HU172526B (en) 1975-11-12 1976-11-11 Process for preparing new derivatives of daunorubicin
SE7612613A SE421212B (en) 1975-11-12 1976-11-11 PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF DAUNORUBICIN
NO763857A NO143349C (en) 1975-11-12 1976-11-11 ANALOGUE PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF DAUNORUBICIN.
YU02778/76A YU277876A (en) 1975-11-12 1976-11-12 Process for obtaining new derivatives of daunorubicin
DE2651773A DE2651773C3 (en) 1975-11-12 1976-11-12 14-Acyloxy-daunorubicins, processes for their preparation and pharmaceutical compositions containing these compounds
AT842876A AT347583B (en) 1975-11-12 1976-11-12 PROCESS FOR THE PRODUCTION OF NEW DAUNORUBICIN DERIVATIVES AND THEIR ACID ADDITION SALT
FI763251A FI62316C (en) 1975-11-12 1976-11-12 FOERFARANDE FOER FRAMSTAELLNING AV DI- ELLER TRISUBSTITUERADE ESTRAR AV DAUNORUBICINDERIVAT VILKA AER ANVAENDBARA VID BEHANDLING AV TUMOERER
ES453264A ES453264A1 (en) 1975-11-12 1976-11-12 Daunorubicin derivatives
US05/849,761 US4225589A (en) 1975-11-12 1977-11-09 Daunorubicin derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7628977A FR2365345A2 (en) 1976-09-27 1976-09-27 (14)-Acyloxy-daunorubicin derivs. - with antitumour activity

Publications (2)

Publication Number Publication Date
FR2365345A2 true FR2365345A2 (en) 1978-04-21
FR2365345B2 FR2365345B2 (en) 1980-02-01

Family

ID=9178114

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7628977A Granted FR2365345A2 (en) 1975-11-12 1976-09-27 (14)-Acyloxy-daunorubicin derivs. - with antitumour activity

Country Status (1)

Country Link
FR (1) FR2365345A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2434820A1 (en) * 1978-08-29 1980-03-28 Inst Internal Pathologie DNA AND DAUNORUBICIN DERIVATIVE COMPLEXES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2434820A1 (en) * 1978-08-29 1980-03-28 Inst Internal Pathologie DNA AND DAUNORUBICIN DERIVATIVE COMPLEXES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Also Published As

Publication number Publication date
FR2365345B2 (en) 1980-02-01

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