CA1331382C - 5-nitrobenzo [de] isoquinoline-1.3-diones, their preparation and their use - Google Patents
5-nitrobenzo [de] isoquinoline-1.3-diones, their preparation and their useInfo
- Publication number
- CA1331382C CA1331382C CA000549722A CA549722A CA1331382C CA 1331382 C CA1331382 C CA 1331382C CA 000549722 A CA000549722 A CA 000549722A CA 549722 A CA549722 A CA 549722A CA 1331382 C CA1331382 C CA 1331382C
- Authority
- CA
- Canada
- Prior art keywords
- isoquinoline
- dione
- formula
- nitrobenzo
- hydrogen
- 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.)
- Expired - Fee Related
Links
- CWVQFVQNUBOYEE-UHFFFAOYSA-N 5-nitrobenzo[de]isoquinoline-1,3-dione Chemical class C1=CC2=CC([N+](=O)[O-])=CC(C(=O)NC3=O)=C2C3=C1 CWVQFVQNUBOYEE-UHFFFAOYSA-N 0.000 title claims abstract 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims abstract description 5
- 125000004761 (C2-C7) alkylaminocarbonyl group Chemical group 0.000 claims abstract description 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- -1 morpholino, piperidinyl Chemical group 0.000 claims abstract description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 4
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 12
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- DYWWDZQRZYAPHQ-UHFFFAOYSA-N 3-benzoyl-4-ethyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one Chemical compound O1C(=O)C(CC)(C)N(C(=O)C=2C=CC=CC=2)C1C1=CC=CC=C1 DYWWDZQRZYAPHQ-UHFFFAOYSA-N 0.000 claims 1
- MUPBDBWCLGNFCR-UHFFFAOYSA-N 5-amino-2-[2-(dimethylamino)ethyl]-8-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC(N)=CC3=C1 MUPBDBWCLGNFCR-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 4
- 230000000259 anti-tumor effect Effects 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QGNQEODJYRGEJX-UHFFFAOYSA-N 4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)NC(=O)CC2=C1 QGNQEODJYRGEJX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 150000002537 isoquinolines Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000001720 action spectrum Methods 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863635711 DE3635711A1 (de) | 1986-10-21 | 1986-10-21 | 5-nitrobenzo(de)isochinolin-1,3-dione, ihre herstellung und verwendung |
| DEP3635711.1 | 1986-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1331382C true CA1331382C (en) | 1994-08-09 |
Family
ID=6312114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000549722A Expired - Fee Related CA1331382C (en) | 1986-10-21 | 1987-10-20 | 5-nitrobenzo [de] isoquinoline-1.3-diones, their preparation and their use |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5552544A (enExample) |
| EP (1) | EP0268093B1 (enExample) |
| JP (1) | JPS63104963A (enExample) |
| AT (1) | ATE76069T1 (enExample) |
| AU (1) | AU592474B2 (enExample) |
| CA (1) | CA1331382C (enExample) |
| DE (2) | DE3635711A1 (enExample) |
| ES (1) | ES2037055T3 (enExample) |
| ZA (1) | ZA877859B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3939372A1 (de) * | 1989-11-29 | 1991-06-06 | Knoll Ag | Mitonafide-infusionsloesung |
| DE3942280A1 (de) * | 1989-12-21 | 1991-06-27 | Knoll Ag | N-substituierte naphthalimide, ihre herstellung und verwendung |
| US5235045A (en) * | 1992-03-19 | 1993-08-10 | Microbiomed Corporation | Non-azo naphthalimide dyes |
| US5766600A (en) * | 1993-08-09 | 1998-06-16 | Microbiomed Corporation | Non-azo naphtalimide dyes and uses for same |
| AU728523C (en) | 1996-10-21 | 2001-08-09 | Nps Pharmaceuticals, Inc. | Neurotrophin antagonist compositions |
| DE19714161A1 (de) * | 1997-04-05 | 1998-10-08 | Emtec Magnetics Gmbh | Magnetischer Aufzeichnungsträger |
| AU760136B2 (en) * | 1998-11-25 | 2003-05-08 | Merck Patent Gmbh | Substituted benzo(DE)isoquinoline-1,3-diones |
| MY164077A (en) * | 1999-05-13 | 2017-11-30 | Pharma Mar Sa | Compositions and uses of et743 for treating cancer |
| US6492380B1 (en) * | 1999-05-17 | 2002-12-10 | Queen's University At Kingston | Method of inhibiting neurotrophin-receptor binding |
| US6468990B1 (en) * | 1999-05-17 | 2002-10-22 | Queen's University At Kingston | Method of inhibiting binding of nerve growth factor to p75 NTR receptor |
| MXPA02011319A (es) * | 2000-05-15 | 2003-06-06 | Pharma Mar Sa | Analogos antitumorales de ecteinascidina 743. |
| WO2002036135A2 (en) * | 2000-11-06 | 2002-05-10 | Pharma Mar, S.A. | Compositions for antitumour treatment containing ecteinascidin 743 |
| DE10101319A1 (de) * | 2001-01-09 | 2002-07-18 | Schering Ag | Morphometrisches Gewebe- oder Zellpräparat |
| GB0202544D0 (en) * | 2002-02-04 | 2002-03-20 | Pharma Mar Sa | The synthesis of naturally occuring ecteinascidins and related compounds |
| US6693198B2 (en) * | 2002-04-22 | 2004-02-17 | Xanthus Life Sciences, Inc. | Amonafide salts |
| US20040082788A1 (en) * | 2002-07-08 | 2004-04-29 | Chemgenex Therapeutics, Inc. | Naphthalimide synthesis including amonafide synthesis and pharmaceutical preparations thereof |
| GB0312407D0 (en) * | 2003-05-29 | 2003-07-02 | Pharma Mar Sau | Treatment |
| GB0324201D0 (en) * | 2003-10-15 | 2003-11-19 | Pharma Mar Sau | Improved antitumoral combinations |
| JP2007511499A (ja) * | 2003-11-13 | 2007-05-10 | ファーマ・マール・エス・アー・ウー | コンビネーション |
| JP2007511509A (ja) * | 2003-11-14 | 2007-05-10 | ファルマ・マール・ソシエダード・アノニマ | Ｅｔ−７４３およびパクリタキセルの使用を含むガンの併用療法 |
| GB0326486D0 (en) * | 2003-11-14 | 2003-12-17 | Pharma Mar Sau | Combination treatment |
| JP2007536283A (ja) * | 2004-05-05 | 2007-12-13 | ユニバイオスクリーン エス．アー． | ナフタルイミド誘導体、それらの製造方法、およびそれらの医薬組成物 |
| JP2008505862A (ja) * | 2004-07-09 | 2008-02-28 | ファルマ、マール、ソシエダード、アノニマ | 予後分子マーカー |
| WO2006035244A2 (en) * | 2004-09-29 | 2006-04-06 | Pharma Mar S.A., Sociedad Unipersonal | Ecteinascidin compounds as anti -inflammatory agents |
| RS50822B (sr) * | 2004-10-26 | 2010-08-31 | Pharma Mar S.A., Sociedad Unipersonal | Pegilovani lipozomalni doksorubicin u kombinaciji sa ekteinescidinom 743 |
| KR101188691B1 (ko) * | 2004-10-29 | 2012-10-09 | 파르마 마르 에스.에이. | 엑티나시딘 및 디사카라이드를 포함하는 제제 |
| US7947839B2 (en) * | 2004-12-01 | 2011-05-24 | Genentech, Inc. | Heterocyclic-substituted bis-1,8 naphthalimide compounds, antibody drug conjugates, and methods of use |
| US20070099900A1 (en) | 2005-09-15 | 2007-05-03 | Painceptor Pharma Corporation | Methods of modulating neurotrophin-mediated activity |
| GB0522082D0 (en) * | 2005-10-31 | 2005-12-07 | Pharma Mar Sa | Formulations |
| JP2009536169A (ja) * | 2006-05-05 | 2009-10-08 | ユニバイオスクリーン エス．アー． | ５−尿素置換ナフタルイミド誘導体、製造方法、および癌治療用医薬組成物 |
| WO2009050303A1 (en) * | 2007-10-19 | 2009-04-23 | Pharma Mar, S.A. | Prognostic molecular markers for et-743 treatment |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES459497A1 (es) * | 1977-06-04 | 1978-04-16 | Made Labor Sa | Un metodo para la preparacion industrial de naftalimidas y sus derivados. |
| DE2944867A1 (de) * | 1979-11-07 | 1981-05-27 | Hoechst Ag, 6000 Frankfurt | Kationische verbindungen der naphthalimid-reihe, verfahren zu deren herstellung und deren verwendung |
| US4614820A (en) * | 1983-04-01 | 1986-09-30 | Warner-Lambert Co. | 3,6-disubstituted-1,8-naphthalimides |
| EP0125439B1 (en) * | 1983-04-01 | 1990-01-24 | Warner-Lambert Company | 3,6-disubstituted-1,8-naphthalimides and methods for their production and use |
| DE3614414A1 (de) * | 1986-04-29 | 1987-11-05 | Knoll Ag | Neue benzo(de)isochinolin-1,3-dione, ihre herstellung und verwendung |
| US4782064A (en) * | 1986-07-21 | 1988-11-01 | American Cyanamid Co. | 2-heteroaryl-alkyl-1H-benz[de]-isoquinoline-1,3(2H)-diones |
-
1986
- 1986-10-21 DE DE19863635711 patent/DE3635711A1/de not_active Withdrawn
-
1987
- 1987-10-20 DE DE87115310T patent/DE3779053D1/de not_active Expired - Lifetime
- 1987-10-20 AT AT87115310T patent/ATE76069T1/de not_active IP Right Cessation
- 1987-10-20 ZA ZA877859A patent/ZA877859B/xx unknown
- 1987-10-20 ES ES198787115310T patent/ES2037055T3/es not_active Expired - Lifetime
- 1987-10-20 EP EP87115310A patent/EP0268093B1/de not_active Expired - Lifetime
- 1987-10-20 JP JP62262939A patent/JPS63104963A/ja active Pending
- 1987-10-20 CA CA000549722A patent/CA1331382C/en not_active Expired - Fee Related
- 1987-10-21 AU AU79990/87A patent/AU592474B2/en not_active Ceased
-
1990
- 1990-06-04 US US07/533,944 patent/US5552544A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0268093B1 (de) | 1992-05-13 |
| ES2037055T3 (es) | 1993-06-16 |
| AU7999087A (en) | 1988-04-28 |
| ZA877859B (en) | 1989-06-28 |
| ATE76069T1 (de) | 1992-05-15 |
| JPS63104963A (ja) | 1988-05-10 |
| AU592474B2 (en) | 1990-01-11 |
| EP0268093A1 (de) | 1988-05-25 |
| US5552544A (en) | 1996-09-03 |
| DE3635711A1 (de) | 1988-04-28 |
| DE3779053D1 (enExample) | 1992-06-17 |
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