AU1236401A - Heterocyclic cytotoxic agents - Google Patents

Heterocyclic cytotoxic agents Download PDF

Info

Publication number: AU1236401A
Authority: AU; Australia
Prior art keywords: compound; alkyl; alkoxy; hydrogen; hydroxy
Prior art date: 1999-10-29
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

Application number

AU12364/01A

Other languages

English (en)

Inventor

Edmond J. Lavoie

Leroy Fong Liu

Younong Yu

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.)

Rutgers State University of New Jersey

Original Assignee

Rutgers State University of New Jersey

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.)

1999-10-29

Filing date

2000-10-26

Publication date

2001-05-14

2000-10-26 Application filed by Rutgers State University of New Jersey filed Critical Rutgers State University of New Jersey

2001-05-14 Publication of AU1236401A publication Critical patent/AU1236401A/en

Status Abandoned legal-status Critical Current

Links

229940127089 cytotoxic agent Drugs 0.000 title description 5
239000002254 cytotoxic agent Substances 0.000 title description 4
231100000599 cytotoxic agent Toxicity 0.000 title description 4
125000000623 heterocyclic group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 154
229910052739 hydrogen Inorganic materials 0.000 claims description 98
-1 nitro, hydroxy Chemical group 0.000 claims description 98
239000001257 hydrogen Substances 0.000 claims description 80
125000000217 alkyl group Chemical group 0.000 claims description 58
125000003545 alkoxy group Chemical group 0.000 claims description 51
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
125000005843 halogen group Chemical group 0.000 claims description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 36
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 32
206010028980 Neoplasm Diseases 0.000 claims description 31
125000003118 aryl group Chemical group 0.000 claims description 27
201000011510 cancer Diseases 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
238000000034 method Methods 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 10
230000000844 anti-bacterial effect Effects 0.000 claims description 9
230000000843 anti-fungal effect Effects 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
125000005505 thiomorpholino group Chemical group 0.000 claims description 8
229940121375 antifungal agent Drugs 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
230000000842 anti-protozoal effect Effects 0.000 claims description 6
239000003904 antiprotozoal agent Substances 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
DZVDICCNYQNJJC-UHFFFAOYSA-N 2,3,8-trimethoxy-9-phenylmethoxynaphtho[1,2-c]cinnoline Chemical compound COC=1C=C2N=NC3=C4C=C(OC)C(OC)=CC4=CC=C3C2=CC=1OCC1=CC=CC=C1 DZVDICCNYQNJJC-UHFFFAOYSA-N 0.000 claims description 5
230000012010 growth Effects 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
OMUIGKAGIWPDCY-UHFFFAOYSA-N 2,3,8,9-tetramethoxynaphtho[1,2-c]cinnoline Chemical compound COC1=C(OC)C=C2N=NC3=C(C=C(C(OC)=C4)OC)C4=CC=C3C2=C1 OMUIGKAGIWPDCY-UHFFFAOYSA-N 0.000 claims description 4
YPLVCEDAZWQZQO-UHFFFAOYSA-N 2,3,8-trimethoxynaphtho[1,2-c]cinnoline Chemical compound C1=C(OC)C(OC)=CC2=CC=C3C4=CC=C(OC)C=C4N=NC3=C21 YPLVCEDAZWQZQO-UHFFFAOYSA-N 0.000 claims description 4
YUYRZQOQHINLNO-UHFFFAOYSA-N 2,3,9-trimethoxynaphtho[1,2-c]cinnoline Chemical compound C1=C(OC)C(OC)=CC2=CC=C(C=3C(=CC=C(C=3)OC)N=N3)C3=C21 YUYRZQOQHINLNO-UHFFFAOYSA-N 0.000 claims description 4
IMPABAXTBFQROU-UHFFFAOYSA-N 2-methoxy-8,9-methylenedioxydibenzo[c,h]cinnoline Chemical compound C1=C2OCOC2=CC2=NN=C3C4=CC=C(OC)C=C4C=CC3=C21 IMPABAXTBFQROU-UHFFFAOYSA-N 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
230000010261 cell growth Effects 0.000 claims description 4
238000001727 in vivo Methods 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
DZPAHDGQIJWIKC-UHFFFAOYSA-N 2,3,8-trimethoxynaphtho[1,2-c]cinnolin-9-ol Chemical compound COC1=C(OC)C=C2C=CC3=C(C=C(C(OC)=C4)O)C4=NN=C3C2=C1 DZPAHDGQIJWIKC-UHFFFAOYSA-N 0.000 claims description 3
BNKLNOIJZZDUHZ-UHFFFAOYSA-N 2,3-dimethoxy-8,9-methylenedioxy-dibenzo[c,h]cinnoline Chemical compound C1=C2N=NC3=C(C=C(C(OC)=C4)OC)C4=CC=C3C2=CC2=C1OCO2 BNKLNOIJZZDUHZ-UHFFFAOYSA-N 0.000 claims description 3
CTZYGJFBHJAZBE-UHFFFAOYSA-N 2,3-dimethoxynaphtho[1,2-c]cinnoline Chemical compound C1=CC=C2N=NC3=C(C=C(C(OC)=C4)OC)C4=CC=C3C2=C1 CTZYGJFBHJAZBE-UHFFFAOYSA-N 0.000 claims description 3
230000000840 anti-viral effect Effects 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
238000000338 in vitro Methods 0.000 claims description 3
238000013160 medical therapy Methods 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 20
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 11
125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 243
239000000243 solution Substances 0.000 description 90
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 80
239000000203 mixture Substances 0.000 description 75
238000005481 NMR spectroscopy Methods 0.000 description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
239000012044 organic layer Substances 0.000 description 27
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
239000012267 brine Substances 0.000 description 22
239000012043 crude product Substances 0.000 description 22
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
239000000543 intermediate Substances 0.000 description 21
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 17
239000011734 sodium Substances 0.000 description 17
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
102000003915 DNA Topoisomerases Human genes 0.000 description 15
108090000323 DNA Topoisomerases Proteins 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
238000001816 cooling Methods 0.000 description 15
239000003054 catalyst Substances 0.000 description 14
210000004027 cell Anatomy 0.000 description 14
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
125000000753 cycloalkyl group Chemical group 0.000 description 12
231100000614 poison Toxicity 0.000 description 12
239000002574 poison Substances 0.000 description 12
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 12
239000007788 liquid Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
101710183280 Topoisomerase Proteins 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
229940079593 drug Drugs 0.000 description 9
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239000002244 precipitate Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
229910021589 Copper(I) bromide Inorganic materials 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 8
239000002552 dosage form Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
238000010992 reflux Methods 0.000 description 8
235000010288 sodium nitrite Nutrition 0.000 description 8
239000003826 tablet Substances 0.000 description 8
RPRQHHJLRLEIOK-UHFFFAOYSA-N 2-(6,7-dimethoxynaphthalen-2-yl)aniline Chemical compound C1=C2C=C(OC)C(OC)=CC2=CC=C1C1=CC=CC=C1N RPRQHHJLRLEIOK-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 6
KKMPSGJPCCJYRV-UHFFFAOYSA-N Nitidine Chemical compound C1=C2C3=[N+](C)C=C4C=C(OC)C(OC)=CC4=C3C=CC2=CC2=C1OCO2 KKMPSGJPCCJYRV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000003556 assay Methods 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000012954 diazonium Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 6
239000011698 potassium fluoride Substances 0.000 description 6
235000003270 potassium fluoride Nutrition 0.000 description 6
KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 6
229910000080 stannane Inorganic materials 0.000 description 6
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
KCOBIBRGPCFIGF-UHFFFAOYSA-N 1-bromo-4-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(Br)C([N+]([O-])=O)=C1 KCOBIBRGPCFIGF-UHFFFAOYSA-N 0.000 description 5
MVXFWIJIPARTPT-UHFFFAOYSA-N 2-(6,7-dimethoxynaphthalen-2-yl)-4,5-dimethoxyaniline Chemical compound C1=C(OC)C(OC)=CC(N)=C1C1=CC=C(C=C(OC)C(OC)=C2)C2=C1 MVXFWIJIPARTPT-UHFFFAOYSA-N 0.000 description 5
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108010046308 Type II DNA Topoisomerases Proteins 0.000 description 5
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229940127093 camptothecin Drugs 0.000 description 5
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DUHXKKFPSASCAQ-UHFFFAOYSA-N 2-(6,7-dimethoxynaphthalen-2-yl)-4-methoxyaniline Chemical compound COC1=CC=C(N)C(C=2C=C3C=C(OC)C(OC)=CC3=CC=2)=C1 DUHXKKFPSASCAQ-UHFFFAOYSA-N 0.000 description 4
PXMNNSNFKYHGSG-UHFFFAOYSA-N 2-(6,7-dimethoxynaphthalen-2-yl)-5-methoxyaniline Chemical compound NC1=CC(OC)=CC=C1C1=CC=C(C=C(OC)C(OC)=C2)C2=C1 PXMNNSNFKYHGSG-UHFFFAOYSA-N 0.000 description 4
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OIAMIMPHJVFABE-UHFFFAOYSA-N 6-(6,7-dimethoxynaphthalen-2-yl)-1,3-benzodioxol-5-amine Chemical compound C1=C2C=C(OC)C(OC)=CC2=CC=C1C(C(=C1)N)=CC2=C1OCO2 OIAMIMPHJVFABE-UHFFFAOYSA-N 0.000 description 4
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DJLDZTLFZFWEPH-UHFFFAOYSA-N trimethyl-(6-nitro-1,3-benzodioxol-5-yl)stannane Chemical compound C1=C([N+]([O-])=O)C([Sn](C)(C)C)=CC2=C1OCO2 DJLDZTLFZFWEPH-UHFFFAOYSA-N 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
Virology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

AU12364/01A 1999-10-29 2000-10-26 Heterocyclic cytotoxic agents Abandoned AU1236401A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US16254099P	1999-10-29	1999-10-29
US60162540		1999-10-29
PCT/US2000/029583 WO2001032631A2 (en)	1999-10-29	2000-10-26	Heterocyclic cytotoxic agents

Publications (1)

Publication Number	Publication Date
AU1236401A true AU1236401A (en)	2001-05-14

Family

ID=22586069

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU12364/01A Abandoned AU1236401A (en)	1999-10-29	2000-10-26	Heterocyclic cytotoxic agents

Country Status (6)

Country	Link
EP (1)	EP1228045A2 (de)
JP (1)	JP2003513079A (de)
AR (1)	AR026267A1 (de)
AU (1)	AU1236401A (de)
CA (1)	CA2389312A1 (de)
WO (1)	WO2001032631A2 (de)

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Publication number	Priority date	Publication date	Assignee	Title
EP1453812B1 (de)	2001-11-14	2008-08-20	Rutgers, The State University	Cytotoxische mittel
MXPA04004607A (es) *	2001-11-14	2004-09-10	Univ Rutgers	Agentes de venenos de topoisomerasa solubilizados.
AU2002364953A1 (en)	2001-11-14	2003-06-17	Edmond J. Lavoie	Topoisomerase poison agents
DE60235287D1 (de) *	2001-11-14	2010-03-25	Univ Rutgers	Löslich gemachte topoisomerase-gifte
US6989387B2 (en)	2002-08-09	2006-01-24	Rutgers, The State University Of New Jersey	Nitro and amino substituted topoisomerase agents
AU2003268075A1 (en) *	2002-08-09	2004-02-25	Edmond J. Lavoie	Nitro and amino substituted dibenzonaphthyridines as topoisomerase agents
US6992088B2 (en)	2002-08-09	2006-01-31	Rutgers, The State University Of New Jersey	Nitro and amino substituted heterocycles as topoisomerase I targeting agents
CA2510337C (en)	2002-11-12	2013-01-08	Rutgers, The State University Of New Jersey	Topoisomerase-targeting agents
CA2512000C (en) *	2002-12-26	2011-08-09	Eisai Co., Ltd.	Selective estrogen receptor modulator
DE102008022221A1 (de)	2008-05-06	2009-11-12	Universität des Saarlandes	Inhibitoren der humanen Aldosteronsynthase CYP11B2
TW201038578A (en)	2009-01-30	2010-11-01	Univ Rutgers	Methods to treat cancer
DK2403856T3 (da)	2009-03-06	2013-04-08	Univ Rutgers	Methylendioxybenzo[i]phenanthridinderivater anvendt til behandling af cancer
WO2010127363A1 (en)	2009-05-01	2010-11-04	Rutgers, The State University Of New Jersey	Toposiomerase inhibitors
US8541404B2 (en)	2009-11-09	2013-09-24	Elexopharm Gmbh	Inhibitors of the human aldosterone synthase CYP11B2
US9421264B2 (en)	2014-03-28	2016-08-23	Duke University	Method of treating cancer using selective estrogen receptor modulators
FI3834824T3 (fi)	2014-03-28	2025-12-05	Univ Duke	Estrogeenireseptoripositiivisen rintasyövän hoito selektiivisellä estrogeenireseptorin modulaattorilla
US11091498B2 (en)	2016-04-04	2021-08-17	Rutgers, The State University Of New Jersey	Topoisomerase poisons

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Publication number	Priority date	Publication date	Assignee	Title
WO1998045272A1 (en) *	1997-04-07	1998-10-15	Latrobe University	Topoisomerase inhibitors

2000
- 2000-10-26 WO PCT/US2000/029583 patent/WO2001032631A2/en not_active Ceased
- 2000-10-26 AU AU12364/01A patent/AU1236401A/en not_active Abandoned
- 2000-10-26 JP JP2001534782A patent/JP2003513079A/ja not_active Withdrawn
- 2000-10-26 CA CA002389312A patent/CA2389312A1/en not_active Abandoned
- 2000-10-26 EP EP00973917A patent/EP1228045A2/de not_active Withdrawn
- 2000-10-27 AR ARP000105664A patent/AR026267A1/es unknown

Also Published As

Publication number	Publication date
AR026267A1 (es)	2003-02-05
JP2003513079A (ja)	2003-04-08
EP1228045A2 (de)	2002-08-07
WO2001032631A3 (en)	2002-02-21
WO2001032631A2 (en)	2001-05-10
CA2389312A1 (en)	2001-05-10

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AU748624B2 (en)	2002-06-06	Heterocyclic cytotoxic agents
US7858627B2 (en)	2010-12-28	Topoisomerase-targeting agents
US6989387B2 (en)	2006-01-24	Nitro and amino substituted topoisomerase agents
AU2002365161B2 (en)	2008-07-03	Solubilized topoisomerase poison agents
US6063801A (en)	2000-05-16	Heterocyclic topoisomerase poisons