FR2478633A1 - 13-(1-hydroxy-2,2,6,6-tetramethyl-piperylidenyl-4) hydrazone du chlorhydrate de rubomycine a centre paramagnetique, son procede de preparation, et son application therapeutique - Google Patents
13-(1-hydroxy-2,2,6,6-tetramethyl-piperylidenyl-4) hydrazone du chlorhydrate de rubomycine a centre paramagnetique, son procede de preparation, et son application therapeutique Download PDFInfo
- Publication number
- FR2478633A1 FR2478633A1 FR8022569A FR8022569A FR2478633A1 FR 2478633 A1 FR2478633 A1 FR 2478633A1 FR 8022569 A FR8022569 A FR 8022569A FR 8022569 A FR8022569 A FR 8022569A FR 2478633 A1 FR2478633 A1 FR 2478633A1
- Authority
- FR
- France
- Prior art keywords
- rubomycin
- base
- compound
- hydrazone
- hydrochloride
- 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
- GUGHGUXZJWAIAS-QQYBVWGSSA-N Daunorubicin hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 GUGHGUXZJWAIAS-QQYBVWGSSA-N 0.000 title claims abstract description 49
- 229930191933 Rubomycin Natural products 0.000 title claims abstract description 47
- 150000007857 hydrazones Chemical class 0.000 title claims abstract description 14
- 230000005414 paramagnetic center Effects 0.000 title claims abstract description 7
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 238000000926 separation method Methods 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract 3
- 208000032839 leukemia Diseases 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 11
- 230000012010 growth Effects 0.000 abstract description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 230000003211 malignant effect Effects 0.000 abstract description 3
- 239000008280 blood Substances 0.000 abstract description 2
- 210000004369 blood Anatomy 0.000 abstract description 2
- 230000000771 oncological effect Effects 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 description 14
- 230000000259 anti-tumor effect Effects 0.000 description 14
- 229960000641 zorubicin Drugs 0.000 description 11
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 230000004083 survival effect Effects 0.000 description 8
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960000975 daunorubicin Drugs 0.000 description 6
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 208000007093 Leukemia L1210 Diseases 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000007665 chronic toxicity Effects 0.000 description 3
- 231100000160 chronic toxicity Toxicity 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GYPCWHHQAVLMKO-XXKQIVDLSA-N (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-[(e)-n-[(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ylidene)amino]-c-methylcarbonimidoyl]-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical group Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\N=C1CC(C)(C)N(O)C(C)(C)C1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 GYPCWHHQAVLMKO-XXKQIVDLSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical class O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 231100000682 maximum tolerated dose Toxicity 0.000 description 2
- 201000005404 rubella Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- 206010000830 Acute leukaemia Diseases 0.000 description 1
- 241000194106 Bacillus mycoides Species 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- 208000006332 Choriocarcinoma Diseases 0.000 description 1
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
- 208000000526 Experimental Leukemia Diseases 0.000 description 1
- DMUAPQTXSSNEDD-QALJCMCCSA-N Midecamycin Chemical compound C1[C@](O)(C)[C@@H](OC(=O)CC)[C@H](C)O[C@H]1O[C@H]1[C@H](N(C)C)[C@@H](O)[C@H](O[C@@H]2[C@H]([C@H](OC(=O)CC)CC(=O)O[C@H](C)C/C=C/C=C/[C@H](O)[C@H](C)C[C@@H]2CC=O)OC)O[C@@H]1C DMUAPQTXSSNEDD-QALJCMCCSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000220254 Streptomyces coeruleorubidus Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000001720 action spectrum Methods 0.000 description 1
- 229940009456 adriamycin Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 231100000457 cardiotoxic Toxicity 0.000 description 1
- 230000001451 cardiotoxic effect Effects 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000011132 hemopoiesis Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 229960002757 midecamycin Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- FBTUMDXHSRTGRV-BJISBDEGSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=NNC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-BJISBDEGSA-N 0.000 description 1
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU802893526A RU977462C (ru) | 1980-03-24 | 1980-03-24 | 13-(1-оксил-2,2,6,6-тетраметилпиперилиденил-4)гидразон рубомицина хлоргидрат с парамагнитным центром, проявляющий противоопухолевую активность, и способ его получения |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2478633A1 true FR2478633A1 (fr) | 1981-09-25 |
| FR2478633B1 FR2478633B1 (enExample) | 1983-07-22 |
Family
ID=20882488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8022569A Granted FR2478633A1 (fr) | 1980-03-24 | 1980-10-22 | 13-(1-hydroxy-2,2,6,6-tetramethyl-piperylidenyl-4) hydrazone du chlorhydrate de rubomycine a centre paramagnetique, son procede de preparation, et son application therapeutique |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4332934A (enExample) |
| JP (1) | JPS56133298A (enExample) |
| DE (1) | DE3037884C2 (enExample) |
| FR (1) | FR2478633A1 (enExample) |
| GB (1) | GB2072658B (enExample) |
| IT (1) | IT1134110B (enExample) |
| NL (1) | NL182882C (enExample) |
| RU (1) | RU977462C (enExample) |
| SE (1) | SE449105B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050003008A1 (en) * | 1997-09-23 | 2005-01-06 | Natalya Rapoport | Method of in vivo drug targeting to solid tumors via acoustically triggered drug delivery in polymeric micelles |
| US7910607B2 (en) * | 2006-03-10 | 2011-03-22 | The Trustees Of California State University | Nitroxide free radical synergized antineoplastic agents |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2235103A1 (en) * | 1973-06-29 | 1975-01-24 | Commissariat Energie Atomique | Marked nitroxide derivatives of saccharides - by reaction of acid nitroxide with halogenated saccharides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1469430A (en) | 1974-12-24 | 1977-04-06 | Farmaceutici Italia | Daunomycin derivatives |
| US4112217A (en) * | 1977-09-02 | 1978-09-05 | Sri International | Bis-hydrazones of daunomycin and adriamycin |
-
1980
- 1980-03-24 RU SU802893526A patent/RU977462C/ru active
- 1980-10-02 SE SE8006901A patent/SE449105B/sv not_active IP Right Cessation
- 1980-10-02 US US06/192,964 patent/US4332934A/en not_active Expired - Lifetime
- 1980-10-07 DE DE3037884A patent/DE3037884C2/de not_active Expired
- 1980-10-07 GB GB8032334A patent/GB2072658B/en not_active Expired
- 1980-10-07 NL NLAANVRAGE8005543,A patent/NL182882C/xx not_active IP Right Cessation
- 1980-10-22 FR FR8022569A patent/FR2478633A1/fr active Granted
- 1980-10-30 IT IT25669/80A patent/IT1134110B/it active
-
1981
- 1981-01-08 JP JP158681A patent/JPS56133298A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2235103A1 (en) * | 1973-06-29 | 1975-01-24 | Commissariat Energie Atomique | Marked nitroxide derivatives of saccharides - by reaction of acid nitroxide with halogenated saccharides |
Also Published As
| Publication number | Publication date |
|---|---|
| SE449105B (sv) | 1987-04-06 |
| RU977462C (ru) | 1995-06-27 |
| DE3037884C2 (de) | 1983-12-29 |
| GB2072658B (en) | 1983-11-02 |
| NL182882B (nl) | 1988-01-04 |
| DE3037884A1 (de) | 1981-10-01 |
| JPS6334879B2 (enExample) | 1988-07-12 |
| IT8025669A0 (it) | 1980-10-30 |
| NL8005543A (nl) | 1981-10-16 |
| FR2478633B1 (enExample) | 1983-07-22 |
| GB2072658A (en) | 1981-10-07 |
| US4332934A (en) | 1982-06-01 |
| IT1134110B (it) | 1986-07-24 |
| NL182882C (nl) | 1988-06-01 |
| SE8006901L (sv) | 1981-09-25 |
| JPS56133298A (en) | 1981-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0154756B1 (fr) | Citrate de vinpocetine et son procédé de préparation | |
| FR2461711A1 (fr) | Composes du 1h-pyrrolo-(2,1-c) (1,4) benzodiazepine-2-acrylamide, leur procede de preparation et compositions pharmaceutiques en contenant | |
| FR2511685A1 (fr) | Complexe platine-diamine, procede d'obtention, application d'un tel complexe pour l'obtention d'un medicament pour le traitement du cancer et medicament ainsi obtenu | |
| LU87290A1 (fr) | Derives de 4'-phosphates de glucosides d'epipodophyllotoxine | |
| EP0039272B1 (fr) | Composé complexe isocitraté du platine, son procédé de préparation et son application thérapeutique | |
| FR2525225A1 (fr) | Nouveaux derives 4'-iodo de glycosides d'anthracycline et leur emploi comme medicament | |
| FR2550791A1 (enExample) | ||
| EP2331555B1 (fr) | Dérives ferroceniques a activite anticancereuse | |
| EP0318392B1 (fr) | Nouveaux dérivés N-(vinblastinoyl-23) d'acide amino-1 méthylphosphonique, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent | |
| FR2478633A1 (fr) | 13-(1-hydroxy-2,2,6,6-tetramethyl-piperylidenyl-4) hydrazone du chlorhydrate de rubomycine a centre paramagnetique, son procede de preparation, et son application therapeutique | |
| EP1140825B1 (fr) | Derives de melatonine et medicament comprenant de tels derives | |
| LU86059A1 (fr) | Nouveaux analogues 6-substitues de la mitomycine | |
| JP2006514064A (ja) | ポルフィリン誘導体 | |
| EP0022730A1 (fr) | Nouvelle classe de composés bis-indoliques utiles comme médicaments et procédé pour leur préparation | |
| BE1001688A5 (fr) | Nouveaux derives de demethoxy-4 anthracycline. | |
| CH616937A5 (en) | Process for producing 9-hydroxyellepticine derivatives | |
| FR2460933A1 (fr) | Derives solubles dans l'eau de la 6,6'-methylene-bis (2,2,4-trimethyl-1,2-dihydroquinoline), leur procede de preparation et leur utilisation dans des compositions pharmaceutiques | |
| CN1059896C (zh) | 肿瘤逆转剂组成物及其制备方法 | |
| FR2510577A1 (fr) | Composes organiques azotes extraits de plantes et leurs derives, leur preparation et leurs utilisations therapeutiques, notamment en tant qu'agents antineoplastiques | |
| EP0172059B1 (fr) | Nouveaux dérivés de l'oxaazaphosphorine, leur procédé de préparation et les compositions pharmaceutiques les renfermant | |
| EP0042348A1 (fr) | Dérivés de l'olivacine et leur application thérapeutique | |
| CN100439372C (zh) | 卟啉衍生物 | |
| FR2516085A1 (fr) | Sels quaternaires de n,n3-di(b-bromopropionyl)-n1,n2-dispirotripiperazinium, procede de preparation desdits sels et medicament a action antitumorale a base d'un tel sel | |
| FR2864959A1 (fr) | Derives de pyranone, leur procede de preparation et leur application en therapeutique, notamment pour le traitement du cancer | |
| WO2022040788A1 (en) | Open-ring and lactone derivatives of unsaturated trihydroxy c-18 fatty acids and pharmaceutical compositions thereof having anti-cancer activity |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |