CN1304380C - 苯并[a]吩嗪－11－酰胺衍生物及它们作为拓扑异构酶Ⅰ和Ⅱ的联合抑制剂的用途 - Google Patents
苯并[a]吩嗪－11－酰胺衍生物及它们作为拓扑异构酶Ⅰ和Ⅱ的联合抑制剂的用途 Download PDFInfo
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- CN1304380C CN1304380C CNB008187096A CN00818709A CN1304380C CN 1304380 C CN1304380 C CN 1304380C CN B008187096 A CNB008187096 A CN B008187096A CN 00818709 A CN00818709 A CN 00818709A CN 1304380 C CN1304380 C CN 1304380C
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- Prior art keywords
- benzo
- azophenlyene
- formic acid
- dimethylamino
- compound
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- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000012266 salt solution Substances 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
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000003579 shift reagent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 201000008261 skin carcinoma Diseases 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000001562 sternum Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- YJSKZIATOGOJEB-UHFFFAOYSA-N thieno[2,3-b]pyrazine Chemical compound C1=CN=C2SC=CC2=N1 YJSKZIATOGOJEB-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
-
- 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
- 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
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9928542.1 | 1999-12-02 | ||
| GBGB9928542.1A GB9928542D0 (en) | 1999-12-02 | 1999-12-02 | Pharmaceutical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1433406A CN1433406A (zh) | 2003-07-30 |
| CN1304380C true CN1304380C (zh) | 2007-03-14 |
Family
ID=10865607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB008187096A Expired - Fee Related CN1304380C (zh) | 1999-12-02 | 2000-12-01 | 苯并[a]吩嗪－11－酰胺衍生物及它们作为拓扑异构酶Ⅰ和Ⅱ的联合抑制剂的用途 |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1240148A1 (xx) |
| JP (1) | JP2003518103A (xx) |
| KR (1) | KR100767613B1 (xx) |
| CN (1) | CN1304380C (xx) |
| AU (1) | AU784397B2 (xx) |
| BR (1) | BR0016093A (xx) |
| CA (1) | CA2392873A1 (xx) |
| GB (2) | GB9928542D0 (xx) |
| HK (1) | HK1046133B (xx) |
| HU (1) | HUP0300392A3 (xx) |
| MX (1) | MXPA02005476A (xx) |
| MY (1) | MY136029A (xx) |
| PL (1) | PL356482A1 (xx) |
| TW (1) | TWI280242B (xx) |
| WO (1) | WO2001046157A1 (xx) |
| ZA (1) | ZA200204296B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2433071A (en) * | 2005-12-05 | 2007-06-13 | Kontrakt Technology Ltd | Organic acids comprising planar conjugated heterocyclic molecular system, & photoelectric layer thereof with rodlike supramolecules for use in solar cell |
| CN102898388B (zh) * | 2012-09-26 | 2014-12-03 | 浙江工业大学 | 一种合成取代苯并[α]吩嗪类化合物的方法 |
| CN103360329B (zh) * | 2013-07-18 | 2015-11-18 | 中国科学院南海海洋研究所 | 一类吩嗪化合物及其在制备抗肿瘤药物中的应用 |
| CN106554321B (zh) * | 2015-09-25 | 2019-05-28 | 陆源 | 一种吩嗪类物质、其制备方法及其应用 |
| CN113461623A (zh) * | 2021-07-14 | 2021-10-01 | 长江大学 | 一种抗病毒化合物及其制备方法和应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998045272A1 (en) * | 1997-04-07 | 1998-10-15 | Latrobe University | Topoisomerase inhibitors |
| US5891886A (en) * | 1992-05-28 | 1999-04-06 | Xenova Limited | Treatment of cancers |
| US5981541A (en) * | 1996-09-23 | 1999-11-09 | Rutgers, The State University Of New Jersey | Substituted heterocycles as anti-tumor agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2136860A1 (en) * | 1992-05-28 | 1993-12-09 | Bruce C. Baguley | Use of n-(2-(dimethylamino)ethyl)acridine-4-carboxamide and its analogues for cancer treatment |
-
1999
- 1999-12-02 GB GBGB9928542.1A patent/GB9928542D0/en not_active Ceased
-
2000
- 2000-12-01 BR BR0016093-8A patent/BR0016093A/pt not_active IP Right Cessation
- 2000-12-01 HU HU0300392A patent/HUP0300392A3/hu unknown
- 2000-12-01 GB GB0215275A patent/GB2373499B/en not_active Expired - Fee Related
- 2000-12-01 PL PL00356482A patent/PL356482A1/xx not_active Application Discontinuation
- 2000-12-01 MY MYPI20005670A patent/MY136029A/en unknown
- 2000-12-01 EP EP00979799A patent/EP1240148A1/en not_active Withdrawn
- 2000-12-01 KR KR1020027007033A patent/KR100767613B1/ko not_active IP Right Cessation
- 2000-12-01 CA CA002392873A patent/CA2392873A1/en not_active Abandoned
- 2000-12-01 WO PCT/GB2000/004609 patent/WO2001046157A1/en active Application Filing
- 2000-12-01 AU AU17184/01A patent/AU784397B2/en not_active Ceased
- 2000-12-01 MX MXPA02005476A patent/MXPA02005476A/es not_active Application Discontinuation
- 2000-12-01 CN CNB008187096A patent/CN1304380C/zh not_active Expired - Fee Related
- 2000-12-01 JP JP2001547068A patent/JP2003518103A/ja active Pending
- 2000-12-02 TW TW089125715A patent/TWI280242B/zh not_active IP Right Cessation
-
2002
- 2002-05-29 ZA ZA200204296A patent/ZA200204296B/en unknown
- 2002-10-10 HK HK02107392.7A patent/HK1046133B/zh not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5891886A (en) * | 1992-05-28 | 1999-04-06 | Xenova Limited | Treatment of cancers |
| US5981541A (en) * | 1996-09-23 | 1999-11-09 | Rutgers, The State University Of New Jersey | Substituted heterocycles as anti-tumor agents |
| WO1998045272A1 (en) * | 1997-04-07 | 1998-10-15 | Latrobe University | Topoisomerase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003518103A (ja) | 2003-06-03 |
| GB2373499A (en) | 2002-09-25 |
| ZA200204296B (en) | 2003-05-29 |
| GB9928542D0 (en) | 2000-02-02 |
| TWI280242B (en) | 2007-05-01 |
| KR100767613B1 (ko) | 2007-10-19 |
| KR20020070305A (ko) | 2002-09-05 |
| GB0215275D0 (en) | 2002-08-14 |
| HUP0300392A2 (hu) | 2003-07-28 |
| MXPA02005476A (es) | 2003-09-22 |
| AU1718401A (en) | 2001-07-03 |
| AU784397B2 (en) | 2006-03-23 |
| WO2001046157A1 (en) | 2001-06-28 |
| EP1240148A1 (en) | 2002-09-18 |
| CN1433406A (zh) | 2003-07-30 |
| CA2392873A1 (en) | 2001-06-28 |
| BR0016093A (pt) | 2002-08-20 |
| HK1046133B (zh) | 2005-04-15 |
| HUP0300392A3 (en) | 2003-09-29 |
| GB2373499B (en) | 2004-11-17 |
| HK1046133A1 (en) | 2002-12-27 |
| PL356482A1 (en) | 2004-06-28 |
| MY136029A (en) | 2008-07-31 |
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