CA2188833A1 - Dihydrodibenzo(de,h)isoquinolines derivatives and their use as anti-cancer agents - Google Patents
Dihydrodibenzo(de,h)isoquinolines derivatives and their use as anti-cancer agentsInfo
- Publication number
- CA2188833A1 CA2188833A1 CA002188833A CA2188833A CA2188833A1 CA 2188833 A1 CA2188833 A1 CA 2188833A1 CA 002188833 A CA002188833 A CA 002188833A CA 2188833 A CA2188833 A CA 2188833A CA 2188833 A1 CA2188833 A1 CA 2188833A1
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- formula
- bis
- compound
- dibenz
- 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.)
- Abandoned
Links
- 239000002246 antineoplastic agent Substances 0.000 title description 2
- 150000002537 isoquinolines Chemical class 0.000 title description 2
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract 2
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract 2
- 235000013350 formula milk Nutrition 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- CKWYOIKYTYWDDP-UHFFFAOYSA-N C1(=CC=CC2=CC3=CC=CC=C3C(=C12)C(=O)O)C(=O)N Chemical compound C1(=CC=CC2=CC3=CC=CC=C3C(=C12)C(=O)O)C(=O)N CKWYOIKYTYWDDP-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KSQMWIGJIDTOFT-UHFFFAOYSA-N anthracene-1,9-dicarboxylic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=C(C=CC=C2)C2=CC3=C1 KSQMWIGJIDTOFT-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 230000036210 malignancy Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- 229910052757 nitrogen Inorganic materials 0.000 description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 10
- 229960004756 ethanol Drugs 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JXASPPWQHFOWPL-UHFFFAOYSA-N Tamarixin Natural products C1=C(O)C(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 JXASPPWQHFOWPL-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 dicarboxylic acid halide Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 101100074846 Caenorhabditis elegans lin-2 gene Proteins 0.000 description 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 101100497386 Mus musculus Cask gene Proteins 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- RUANQJMORZSBEK-UHFFFAOYSA-N anthracene-1,9-dicarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C3C(C(=O)O)=CC=CC3=CC2=C1 RUANQJMORZSBEK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- QBPVGVFLUWAMEQ-UHFFFAOYSA-N 2-(2-hydroxyethyl)-1,2-dihydro-3h-dibenz[de,h]isoquinoline-1,3-dione Chemical compound C1=CC=C2C(C(N(CCO)C3=O)=O)=C4C3=CC=CC4=CC2=C1 QBPVGVFLUWAMEQ-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 101000683586 Clostridium acetobutylicum (strain ATCC 824 / DSM 792 / JCM 1419 / LMG 5710 / VKM B-1787) Reverse rubrerythrin-1 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000011102 Thera Species 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000011717 athymic nude mouse Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000037841 lung tumor Diseases 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- 201000008585 noma Diseases 0.000 description 1
- 238000011580 nude mouse model Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23399894A | 1994-04-28 | 1994-04-28 | |
| US08/233,998 | 1994-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2188833A1 true CA2188833A1 (en) | 1995-11-09 |
Family
ID=22879465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002188833A Abandoned CA2188833A1 (en) | 1994-04-28 | 1995-04-12 | Dihydrodibenzo(de,h)isoquinolines derivatives and their use as anti-cancer agents |
Country Status (11)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6197785B1 (en) | 1997-09-03 | 2001-03-06 | Guilford Pharmaceuticals Inc. | Alkoxy-substituted compounds, methods, and compositions for inhibiting PARP activity |
| US6291425B1 (en) | 1999-09-01 | 2001-09-18 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage |
| US6121278A (en) * | 1997-09-03 | 2000-09-19 | Guilford Pharmaceuticals, Inc. | Di-n-heterocyclic compounds, methods, and compositions for inhibiting parp activity |
| US6380193B1 (en) | 1998-05-15 | 2002-04-30 | Guilford Pharmaceuticals Inc. | Fused tricyclic compounds, methods and compositions for inhibiting PARP activity |
| PT103503B (pt) | 2006-06-19 | 2009-05-18 | Univ Do Porto | Novos derivados do bisnaftalimidopropil, processo para a sua preparação, composições farmacêuticas que os contêm e sua utilização em doenças cancerígenas e parasitárias, nomeadamente leishmanioses, tripanossomíases e malária. |
| CN101638389B (zh) * | 2008-03-03 | 2012-09-05 | 河南大学 | 一种含萘酰亚胺结构的多胺衍生物及其制备方法和应用 |
| CN117074567B (zh) * | 2023-08-25 | 2025-06-27 | 四川汇宇制药股份有限公司 | 高效液相色谱法检测氨磷汀中间体纯度及其有关物质的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0125439B1 (en) * | 1983-04-01 | 1990-01-24 | Warner-Lambert Company | 3,6-disubstituted-1,8-naphthalimides and methods for their production and use |
| DE3707651A1 (de) * | 1987-03-10 | 1988-09-22 | Knoll Ag | Bis-naphthalimide, ihre herstellung und verwendung |
| CA2085598C (en) * | 1990-06-26 | 2002-09-17 | David S. Alberts | 1,2-dihydro-3h-dibenzisoquinoline-1,3-dione anticancer agents |
| JP3543196B2 (ja) * | 1992-09-11 | 2004-07-14 | リサーチ コーポレーション テクノロジーズ インコーポレーテッド | ６−エトキシ−２−［２’−（ジメチルアミノ）エチル］−１，２−ジヒドロ−３Ｈ−ジベンズ（ｄｅｈ）−イソキノリン−１，３−ジオン |
| DE4232739A1 (de) * | 1992-09-30 | 1994-03-31 | Knoll Ag | Neue asymmetrisch substituierte bis-Naphthalimide |
-
1995
- 1995-04-12 CN CN95193192A patent/CN1092185C/zh not_active Expired - Fee Related
- 1995-04-12 SG SG1996008471A patent/SG73418A1/en unknown
- 1995-04-12 AU AU23065/95A patent/AU2306595A/en not_active Abandoned
- 1995-04-12 WO PCT/EP1995/001347 patent/WO1995029895A1/en not_active Application Discontinuation
- 1995-04-12 CA CA002188833A patent/CA2188833A1/en not_active Abandoned
- 1995-04-12 EP EP95916636A patent/EP0757676A1/en not_active Withdrawn
- 1995-04-12 JP JP7527954A patent/JPH09512539A/ja not_active Ceased
- 1995-04-18 TW TW084103805A patent/TW307764B/zh active
- 1995-04-18 IL IL11341595A patent/IL113415A/xx not_active IP Right Cessation
- 1995-04-25 HR HR08/233,998A patent/HRP950250A2/hr not_active Application Discontinuation
- 1995-04-26 ZA ZA953379A patent/ZA953379B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW307764B (enrdf_load_stackoverflow) | 1997-06-11 |
| IL113415A (en) | 1999-11-30 |
| SG73418A1 (en) | 2000-06-20 |
| AU2306595A (en) | 1995-11-29 |
| CN1148851A (zh) | 1997-04-30 |
| IL113415A0 (en) | 1995-07-31 |
| CN1092185C (zh) | 2002-10-09 |
| JPH09512539A (ja) | 1997-12-16 |
| EP0757676A1 (en) | 1997-02-12 |
| HRP950250A2 (en) | 1997-10-31 |
| ZA953379B (en) | 1996-10-28 |
| WO1995029895A1 (en) | 1995-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2854971B2 (ja) | 制癌化合物 | |
| US5981753A (en) | Bis-naphthalimides for the treatment of cancer | |
| US5703089A (en) | Dihydrodibenzisoquinolinediones | |
| JP3176062B2 (ja) | イミダゾアクリジン及び抗腫瘍薬としてのその使用 | |
| CA2188833A1 (en) | Dihydrodibenzo(de,h)isoquinolines derivatives and their use as anti-cancer agents | |
| CA2084643A1 (en) | Bis-naphthalimides anticancer agents | |
| JPH08502050A (ja) | 新規の非対照的に置換されたビス−ナフタルイミド | |
| CA2085598C (en) | 1,2-dihydro-3h-dibenzisoquinoline-1,3-dione anticancer agents | |
| US6187787B1 (en) | Bis(9-aminoacridine) DNA intercalating agents having antitumor activity | |
| JP3543196B2 (ja) | ６−エトキシ−２−［２’−（ジメチルアミノ）エチル］−１，２−ジヒドロ−３Ｈ−ジベンズ（ｄｅｈ）−イソキノリン−１，３−ジオン | |
| JPH06506923A (ja) | 抗癌性剤 | |
| US4062953A (en) | Various 2-substituted-1H-benz[de]isoquinoline-1,3(2H)-diones | |
| AU609605B2 (en) | Intermediates for the preparation of novel substituted benzoselenino {4,3,2-cd} indazoles | |
| WO2005103008A1 (en) | Alkaloid compounds and their use as anti-malarial drugs | |
| CA1256431A (en) | Substituted anthra¬1,9-cd|pyrazol-6-(2h)-ones | |
| AU666847B2 (en) | Bis-naphthalimides containing amino-acid derived linkers as anticancer agents | |
| PL165363B1 (pl) | Sposób wytwarzania nowych pochodnych 6H-Indolo[2,3-b] chinoliny | |
| WO1994005641A1 (en) | 4-SUBSTITUTED 6,9,-BIS (SUBSTITUTED-AMINO) BENZO [g] ISOQUINOLINE-5,10,DIONES |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |