GB2036554A - Anthraquinones for use in therapy - Google Patents
Anthraquinones for use in therapy Download PDFInfo
- Publication number
- GB2036554A GB2036554A GB7923012A GB7923012A GB2036554A GB 2036554 A GB2036554 A GB 2036554A GB 7923012 A GB7923012 A GB 7923012A GB 7923012 A GB7923012 A GB 7923012A GB 2036554 A GB2036554 A GB 2036554A
- Authority
- GB
- United Kingdom
- Prior art keywords
- days
- mice
- survival
- examples
- dosage
- 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.)
- Withdrawn
Links
- 150000004056 anthraquinones Chemical class 0.000 title claims abstract description 16
- 238000002560 therapeutic procedure Methods 0.000 title claims abstract description 7
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 208000032839 leukemia Diseases 0.000 claims abstract description 9
- 201000011510 cancer Diseases 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 159000000021 acetate salts Chemical class 0.000 claims description 2
- 230000001093 anti-cancer Effects 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 241000699670 Mus sp. Species 0.000 description 31
- 230000004083 survival effect Effects 0.000 description 27
- 238000012360 testing method Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 230000037396 body weight Effects 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FVXPBEUYCCZFJT-UHFFFAOYSA-N 9,10-dihydroxy-2,3-dihydroanthracene-1,4-dione Chemical compound C1=CC=C2C(O)=C(C(=O)CCC3=O)C3=C(O)C2=C1 FVXPBEUYCCZFJT-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 101100005765 Arabidopsis thaliana CDF1 gene Proteins 0.000 description 5
- 101100007579 Arabidopsis thaliana CPP1 gene Proteins 0.000 description 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 5
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 5
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 5
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 208000003747 lymphoid leukemia Diseases 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- -1 anthraquinone compounds Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 208000006552 Lewis Lung Carcinoma Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 230000036210 malignancy Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000031648 Body Weight Changes Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000218196 Persea Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 210000003567 ascitic fluid Anatomy 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000004579 body weight change Effects 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 201000005787 hematologic cancer Diseases 0.000 description 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical group OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7708452A SE7708452L (sv) | 1977-07-22 | 1977-07-22 | Komposition innehallande en antrakinonforening |
| ZA00774443A ZA774443B (en) | 1977-07-22 | 1977-07-22 | Anthrquinone compounds as anti-cancer agents |
| JP9316877A JPS5428827A (en) | 1977-07-22 | 1977-08-02 | Anthraquinone compound as cancer controlling agent |
| BE179924A BE857494R (fr) | 1977-07-22 | 1977-08-04 | Composes d'anthraquinone utiles pour la teinture et textiles et comme agents a activite contre la leucemie |
| FR7724214A FR2399244A2 (fr) | 1977-07-22 | 1977-08-05 | Compositions a base de composes anthraquinoniques utilises comme agents anticancer |
| GB7923012A GB2036554A (en) | 1977-07-22 | 1978-06-21 | Anthraquinones for use in therapy |
| GB7827474A GB2000029B (en) | 1977-07-22 | 1978-06-21 | Anthraquinones for cancer therapy |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7708452A SE7708452L (sv) | 1977-07-22 | 1977-07-22 | Komposition innehallande en antrakinonforening |
| ZA00774443A ZA774443B (en) | 1977-07-22 | 1977-07-22 | Anthrquinone compounds as anti-cancer agents |
| JP9316877A JPS5428827A (en) | 1977-07-22 | 1977-08-02 | Anthraquinone compound as cancer controlling agent |
| BE179924A BE857494R (fr) | 1977-07-22 | 1977-08-04 | Composes d'anthraquinone utiles pour la teinture et textiles et comme agents a activite contre la leucemie |
| FR7724214A FR2399244A2 (fr) | 1977-07-22 | 1977-08-05 | Compositions a base de composes anthraquinoniques utilises comme agents anticancer |
| GB7923012A GB2036554A (en) | 1977-07-22 | 1978-06-21 | Anthraquinones for use in therapy |
| GB7827474A GB2000029B (en) | 1977-07-22 | 1978-06-21 | Anthraquinones for cancer therapy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2036554A true GB2036554A (en) | 1980-07-02 |
Family
ID=27560757
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7923012A Withdrawn GB2036554A (en) | 1977-07-22 | 1978-06-21 | Anthraquinones for use in therapy |
| GB7827474A Expired GB2000029B (en) | 1977-07-22 | 1978-06-21 | Anthraquinones for cancer therapy |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7827474A Expired GB2000029B (en) | 1977-07-22 | 1978-06-21 | Anthraquinones for cancer therapy |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5428827A (fr) |
| BE (1) | BE857494R (fr) |
| FR (1) | FR2399244A2 (fr) |
| GB (2) | GB2036554A (fr) |
| SE (1) | SE7708452L (fr) |
| ZA (1) | ZA774443B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991005824A1 (fr) * | 1989-10-13 | 1991-05-02 | National Research Development Corporation | Composes anti-cancer |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0154117B1 (fr) * | 1984-02-27 | 1989-12-27 | American Cyanamid Company | Utilisation des anthrachinones 1,4 bi-substitueés pour la fabrication des medicaments immunosuppresives |
| GB9103075D0 (en) * | 1991-02-13 | 1991-03-27 | Washington Odur Ayuko | Trinitrobenzene derivatives and their therapeutic use |
| IE920754A1 (en) * | 1991-03-08 | 1992-09-09 | Univ Vermont | 6,9 BIS(SUBSTITUTED-AMINO) BENZO[g]-ISOQUINOLINE-5,10-DIONES |
| US5436243A (en) * | 1993-11-17 | 1995-07-25 | Research Triangle Institute Duke University | Aminoanthraquinone derivatives to combat multidrug resistance |
-
1977
- 1977-07-22 ZA ZA00774443A patent/ZA774443B/xx unknown
- 1977-07-22 SE SE7708452A patent/SE7708452L/ not_active Application Discontinuation
- 1977-08-02 JP JP9316877A patent/JPS5428827A/ja active Pending
- 1977-08-04 BE BE179924A patent/BE857494R/fr active
- 1977-08-05 FR FR7724214A patent/FR2399244A2/fr active Granted
-
1978
- 1978-06-21 GB GB7923012A patent/GB2036554A/en not_active Withdrawn
- 1978-06-21 GB GB7827474A patent/GB2000029B/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991005824A1 (fr) * | 1989-10-13 | 1991-05-02 | National Research Development Corporation | Composes anti-cancer |
| US5132327A (en) * | 1989-10-13 | 1992-07-21 | National Research Development Corporation | Anti-cancer compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5428827A (en) | 1979-03-03 |
| BE857494R (fr) | 1978-02-06 |
| ZA774443B (en) | 1978-06-28 |
| SE7708452L (sv) | 1979-01-23 |
| FR2399244A2 (fr) | 1979-03-02 |
| GB2000029A (en) | 1979-01-04 |
| FR2399244B2 (fr) | 1982-04-23 |
| GB2000029B (en) | 1982-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |