FR2365346A2 - (14)-Acyloxy-daunorubicin derivs. - with antitumour activity - Google Patents
(14)-Acyloxy-daunorubicin derivs. - with antitumour activityInfo
- Publication number
- FR2365346A2 FR2365346A2 FR7628978A FR7628978A FR2365346A2 FR 2365346 A2 FR2365346 A2 FR 2365346A2 FR 7628978 A FR7628978 A FR 7628978A FR 7628978 A FR7628978 A FR 7628978A FR 2365346 A2 FR2365346 A2 FR 2365346A2
- 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
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.
Priority Applications (24)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7628978A FR2365346A2 (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 |
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 |
PH19114A PH13709A (en) | 1975-11-12 | 1976-11-10 | Daunorubicin derivatives and pharmaceutical compositions containing same |
GB46807/76A GB1525180A (en) | 1975-11-12 | 1976-11-10 | Daunorubicin derivatives |
JP13510676A JPS5285161A (en) | 1975-11-12 | 1976-11-10 | Daunorbicine derivatives |
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 |
AR265428A AR213419A1 (en) | 1975-11-12 | 1976-11-11 | PROCEDURE FOR PREPARING NEW DAUNORUBICIN DERIVATIVES |
DK508776A DK508776A (en) | 1975-11-12 | 1976-11-11 | PROCEDURE FOR THE PREPARATION OF DAUNORUBICIN DERIVATIVES OR ACID ADDITIONAL SALTS THEREOF |
NO763857A NO143349C (en) | 1975-11-12 | 1976-11-11 | ANALOGUE PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF DAUNORUBICIN. |
LU76176A LU76176A1 (en) | 1975-11-12 | 1976-11-11 | |
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 |
DE2651773A DE2651773C3 (en) | 1975-11-12 | 1976-11-12 | 14-Acyloxy-daunorubicins, processes for their preparation and pharmaceutical compositions containing these compounds |
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 |
AT842876A AT347583B (en) | 1975-11-12 | 1976-11-12 | PROCESS FOR THE PRODUCTION OF NEW DAUNORUBICIN DERIVATIVES AND THEIR ACID ADDITION SALT |
ES453264A ES453264A1 (en) | 1975-11-12 | 1976-11-12 | Daunorubicin derivatives |
YU02778/76A YU277876A (en) | 1975-11-12 | 1976-11-12 | Process for obtaining new derivatives of daunorubicin |
US05/849,761 US4225589A (en) | 1975-11-12 | 1977-11-09 | Daunorubicin derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7628978A FR2365346A2 (en) | 1976-09-27 | 1976-09-27 | (14)-Acyloxy-daunorubicin derivs. - with antitumour activity |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2365346A2 true FR2365346A2 (en) | 1978-04-21 |
FR2365346B2 FR2365346B2 (en) | 1980-02-01 |
Family
ID=9178115
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7628978A Granted FR2365346A2 (en) | 1975-11-12 | 1976-09-27 | (14)-Acyloxy-daunorubicin derivs. - with antitumour activity |
Country Status (1)
Country | Link |
---|---|
FR (1) | FR2365346A2 (en) |
-
1976
- 1976-09-27 FR FR7628978A patent/FR2365346A2/en active Granted
Also Published As
Publication number | Publication date |
---|---|
FR2365346B2 (en) | 1980-02-01 |
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