RO113469B1 - Derivati de indolopirolocarbazol, procedeu pentru prepararea acestora si compozitie farmaceutica continand acesti derivati - Google Patents
Derivati de indolopirolocarbazol, procedeu pentru prepararea acestora si compozitie farmaceutica continand acesti derivati Download PDFInfo
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- RO113469B1 RO113469B1 RO93-01067A RO9301067A RO113469B1 RO 113469 B1 RO113469 B1 RO 113469B1 RO 9301067 A RO9301067 A RO 9301067A RO 113469 B1 RO113469 B1 RO 113469B1
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- 238000004519 manufacturing process Methods 0.000 title 1
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- 125000003277 amino group Chemical group 0.000 claims abstract description 50
- 125000003118 aryl group Chemical group 0.000 claims abstract description 47
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 36
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 32
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 31
- 125000001424 substituent group Chemical group 0.000 claims abstract description 29
- 125000005843 halogen group Chemical group 0.000 claims abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
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- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
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- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract description 11
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- 238000000034 method Methods 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 125000000524 functional group Chemical group 0.000 claims description 21
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- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims description 3
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- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 1
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- 125000003282 alkyl amino group Chemical group 0.000 abstract 6
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 52
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 47
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- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
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- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
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- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
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- 229960004393 lidocaine hydrochloride Drugs 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 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
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- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
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- 150000004681 metal hydrides Chemical class 0.000 description 1
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical group ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 238000011275 oncology therapy Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 150000002971 pentose derivatives Chemical group 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 1
- BAQLNPIEFOYKNB-UHFFFAOYSA-N pyridine-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CC=N1 BAQLNPIEFOYKNB-UHFFFAOYSA-N 0.000 description 1
- GAAWKLUURLVNGE-UHFFFAOYSA-N pyrrolo[3,4-c]carbazole Chemical compound C1=CC=C2C3=C4C=NC=C4C=CC3=NC2=C1 GAAWKLUURLVNGE-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
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- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
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- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/044—Pyrrole radicals
-
- 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 Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biotechnology (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Silicon Polymers (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34191691 | 1991-11-29 | ||
| JP6926992 | 1992-02-18 | ||
| JP25730692 | 1992-09-01 | ||
| PCT/JP1992/001549 WO1993011145A1 (en) | 1991-11-29 | 1992-11-27 | Indolopyrrolocarbazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RO113469B1 true RO113469B1 (ro) | 1998-07-30 |
Family
ID=27300000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO93-01067A RO113469B1 (ro) | 1991-11-29 | 1992-11-27 | Derivati de indolopirolocarbazol, procedeu pentru prepararea acestora si compozitie farmaceutica continand acesti derivati |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0545195B1 (enExample) |
| JP (1) | JP2629542B2 (enExample) |
| KR (1) | KR100275976B1 (enExample) |
| AT (1) | ATE130617T1 (enExample) |
| AU (1) | AU650376B2 (enExample) |
| BG (1) | BG61036B1 (enExample) |
| CA (1) | CA2083534C (enExample) |
| CZ (1) | CZ287304B6 (enExample) |
| DE (1) | DE69206242T2 (enExample) |
| DK (1) | DK0545195T3 (enExample) |
| DZ (1) | DZ1634A1 (enExample) |
| ES (1) | ES2079774T3 (enExample) |
| FI (1) | FI106864B (enExample) |
| GR (1) | GR3018527T3 (enExample) |
| HU (3) | HU9203754D0 (enExample) |
| IL (1) | IL103844A (enExample) |
| MX (1) | MX9206847A (enExample) |
| MY (1) | MY114655A (enExample) |
| NO (1) | NO178929C (enExample) |
| NZ (1) | NZ245203A (enExample) |
| PL (1) | PL171468B1 (enExample) |
| RO (1) | RO113469B1 (enExample) |
| RU (1) | RU2117671C1 (enExample) |
| SA (1) | SA93130351B1 (enExample) |
| TW (1) | TW224469B (enExample) |
| WO (1) | WO1993011145A1 (enExample) |
| YU (1) | YU48963B (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995030682A1 (en) * | 1994-05-09 | 1995-11-16 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyprolocarbazole derivative |
| DE69532198T2 (de) * | 1994-05-09 | 2004-08-26 | Banyu Pharmaceutical Co., Ltd. | Antitumor-indolopyrolocarbazolderivat |
| DE69531686T2 (de) * | 1994-06-13 | 2004-07-15 | Banyu Pharmaceutical Co., Ltd. | Glycosyltransferase kodierendes gen und seine verwendung |
| WO1996004293A1 (en) * | 1994-08-02 | 1996-02-15 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyrrolocarbazoles |
| US5591855A (en) * | 1994-10-14 | 1997-01-07 | Cephalon, Inc. | Fused pyrrolocarbazoles |
| US5594009A (en) * | 1994-10-14 | 1997-01-14 | Cephalon, Inc. | Fused pyrrolocarbazoles |
| US5475110A (en) * | 1994-10-14 | 1995-12-12 | Cephalon, Inc. | Fused Pyrrolocarbazoles |
| US5705511A (en) * | 1994-10-14 | 1998-01-06 | Cephalon, Inc. | Fused pyrrolocarbazoles |
| WO1997009339A1 (fr) * | 1995-09-05 | 1997-03-13 | Banyu Pharmaceutical Co., Ltd. | Derives antitumoraux d'indolopyrrolocarbazole |
| US5616724A (en) * | 1996-02-21 | 1997-04-01 | Cephalon, Inc. | Fused pyrrolo[2,3-c]carbazole-6-ones |
| NZ333536A (en) * | 1996-08-22 | 1999-10-28 | Bristol Myers Squibb Co | Cytotoxic amino sugar and related sugar derivatives of indolopyrrolocarbazoles, and use as antitumour agents |
| GB9811624D0 (en) * | 1998-05-29 | 1998-07-29 | Merck Sharp & Dohme | Therapeutic use |
| US6013646A (en) * | 1998-07-02 | 2000-01-11 | Bayer Corporation | Indolocarbazole derivatives useful for the treatment of neurodegenerative diseases and cancer |
| US6858598B1 (en) | 1998-12-23 | 2005-02-22 | G. D. Searle & Co. | Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| US6833373B1 (en) | 1998-12-23 | 2004-12-21 | G.D. Searle & Co. | Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| US6703373B1 (en) | 1999-09-10 | 2004-03-09 | Banyu Pharmaceutical Co., Ltd. | Indolopyrrolocarbazole derivatives and antitumor agents |
| FR2801054B1 (fr) * | 1999-11-17 | 2003-06-13 | Adir | Nouveaux derives de 12,13-(pyranosyl)-indolo[2,3-a]pyrrolo [3,4-c]carbazole et 12,13-(pyranosyl)-furo[3,4-c]indolo [2,3-a]carbazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| TR200302314T4 (tr) | 2000-02-24 | 2004-01-21 | Banyu Pharmaceutical Co., Ltd. | İndolopirolokarbazol türevinin hazırlanması için bir işlem, hazırlık işlemindeki ara ürünler ve ara ürünlerin hazırlanmsı için bir işlem. |
| US6653290B2 (en) | 2000-10-06 | 2003-11-25 | Bristol-Myers Squibb Company | Tumor proliferation inhibitors |
| US6677450B2 (en) | 2000-10-06 | 2004-01-13 | Bristol-Myers Squibb Company | Topoisomerase inhibitors |
| US6610727B2 (en) | 2000-10-06 | 2003-08-26 | Bristol-Myers Squibb Company | Anhydro sugar derivatives of indolocarbazoles |
| US6555677B2 (en) | 2000-10-31 | 2003-04-29 | Merck & Co., Inc. | Phase transfer catalyzed glycosidation of an indolocarbazole |
| RU2003131269A (ru) | 2001-03-22 | 2005-05-10 | Бристол-Маерс Сквибб Компани (Us) | Производные индолопирролокарбазолов и сахаров, цитотоксические и селективные по отношению к топоизомеразе i |
| US6559299B2 (en) | 2001-03-29 | 2003-05-06 | Merck & Co., Inc. | Preparation and isolation of indolocarbazole glycosides |
| PL370866A1 (en) * | 2002-03-26 | 2005-05-30 | Banyu Pharmaceutical Co, Ltd. | Use of antitumor indolopyrrolocarbazole derivative and other anticancer agent in combination |
| CA2398828A1 (en) | 2002-08-09 | 2004-02-09 | Merck & Co., Inc. | A pharmaceutical composition containing an indolopyrrolocarbazole derivative |
| KR20050058444A (ko) * | 2002-08-23 | 2005-06-16 | 반유 세이야꾸 가부시끼가이샤 | 인돌로피롤로카르바졸 유도체의 제조법 |
| WO2005010017A1 (ja) * | 2003-07-24 | 2005-02-03 | Banyu Pharmaceutical Co., Ltd | インドロピロロカルバゾール誘導体及び抗腫瘍剤 |
| US20070042975A1 (en) * | 2003-09-16 | 2007-02-22 | Koji Yamada | Novel indolopyrrolocarbazole derivative with antitumor activity |
| US7241779B2 (en) | 2003-12-23 | 2007-07-10 | Cephalon, Inc. | Fused pyrrolocarbazoles |
| US7169802B2 (en) | 2003-12-23 | 2007-01-30 | Cephalon, Inc. | Fused pyrrolocarbazoles |
| RU2255089C1 (ru) * | 2003-12-26 | 2005-06-27 | Закрытое акционерное общество "АСГЛ-Исследовательские Лаборатории" | Производные гликозидов индоло[2,3-а]пирроло[3,4-с]карбазол-5,7-дионов, обладающие цитотоксической и противоопухолевой активностью |
| ES2326459B1 (es) | 2008-04-08 | 2010-05-28 | Universidad De Oviedo | Indolocarbazoles glicosilados, su procedimiento de obtencion y sus usos. |
| CA2742790C (en) | 2008-11-19 | 2018-02-13 | Cephalon, Inc. | Novel forms of an indazolo[5,4-a]pyrrolo [3,4-c] carbazole compound |
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|---|---|---|---|---|
| US4785085A (en) * | 1986-11-21 | 1988-11-15 | Bristol-Myers Company | Rebeccamycin analogs |
| DE4005969A1 (de) * | 1990-02-26 | 1991-08-29 | Boehringer Mannheim Gmbh | Neue trisubstituierte pyrrole, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
| IL97233A (en) * | 1990-03-06 | 1995-03-30 | Bristol Myers Squibb Co | Rebeccamycin analogs, their production and pharmaceutical compositions containing them |
| JPH0725787B2 (ja) * | 1990-03-06 | 1995-03-22 | ブリストル−マイヤーズ スクイブ カンパニー | 臭化物前駆物質物質供給によるレベカマイシン類似体 |
| CA2108146A1 (en) * | 1991-04-11 | 1992-10-12 | Stuart W. Mccombie | Anti-tumor and anti-psoriatic agents |
-
1992
- 1992-11-20 NZ NZ245203A patent/NZ245203A/en not_active IP Right Cessation
- 1992-11-22 DZ DZ920145A patent/DZ1634A1/fr active
- 1992-11-23 ES ES92119904T patent/ES2079774T3/es not_active Expired - Lifetime
- 1992-11-23 DK DK92119904.8T patent/DK0545195T3/da active
- 1992-11-23 AT AT92119904T patent/ATE130617T1/de not_active IP Right Cessation
- 1992-11-23 CA CA002083534A patent/CA2083534C/en not_active Expired - Fee Related
- 1992-11-23 DE DE69206242T patent/DE69206242T2/de not_active Expired - Fee Related
- 1992-11-23 EP EP92119904A patent/EP0545195B1/en not_active Expired - Lifetime
- 1992-11-23 IL IL103844A patent/IL103844A/xx not_active IP Right Cessation
- 1992-11-24 JP JP4336560A patent/JP2629542B2/ja not_active Expired - Fee Related
- 1992-11-25 TW TW081109448A patent/TW224469B/zh active
- 1992-11-25 MY MYPI92002167A patent/MY114655A/en unknown
- 1992-11-26 AU AU29637/92A patent/AU650376B2/en not_active Ceased
- 1992-11-27 NO NO924593A patent/NO178929C/no not_active IP Right Cessation
- 1992-11-27 HU HU9203754A patent/HU9203754D0/hu unknown
- 1992-11-27 HU HU9203754A patent/HU217611B/hu not_active IP Right Cessation
- 1992-11-27 MX MX9206847A patent/MX9206847A/es unknown
- 1992-11-27 RO RO93-01067A patent/RO113469B1/ro unknown
- 1992-11-27 PL PL92304729A patent/PL171468B1/pl not_active IP Right Cessation
- 1992-11-27 FI FI925422A patent/FI106864B/fi active
- 1992-11-27 YU YU102692A patent/YU48963B/sh unknown
- 1992-11-27 CZ CS19923508A patent/CZ287304B6/cs not_active IP Right Cessation
- 1992-11-27 WO PCT/JP1992/001549 patent/WO1993011145A1/en not_active Ceased
- 1992-11-27 RU RU93050130A patent/RU2117671C1/ru not_active IP Right Cessation
- 1992-11-28 KR KR1019920022729A patent/KR100275976B1/ko not_active Expired - Fee Related
-
1993
- 1993-01-30 SA SA93130351A patent/SA93130351B1/ar unknown
- 1993-07-20 BG BG97970A patent/BG61036B1/bg unknown
-
1995
- 1995-06-08 HU HU95P/P00172P patent/HU211254A9/hu unknown
- 1995-12-22 GR GR950403667T patent/GR3018527T3/el unknown
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