KR100192754B1 - 특정 피라노(3',4':6,7)인돌리지노(1,2-b)퀴놀리논의 제조방법 - Google Patents
특정 피라노(3',4':6,7)인돌리지노(1,2-b)퀴놀리논의 제조방법 Download PDFInfo
- Publication number
- KR100192754B1 KR100192754B1 KR1019930700923A KR930700923A KR100192754B1 KR 100192754 B1 KR100192754 B1 KR 100192754B1 KR 1019930700923 A KR1019930700923 A KR 1019930700923A KR 930700923 A KR930700923 A KR 930700923A KR 100192754 B1 KR100192754 B1 KR 100192754B1
- Authority
- KR
- South Korea
- Prior art keywords
- indolizino
- reaction
- pyrano
- oxopropyl
- methyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 12
- 229930185107 quinolinone Natural products 0.000 title description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- VSJKWCGYPAHWDS-UHFFFAOYSA-N LSM-1442 Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 abstract description 8
- QHTFEANXLNNBOX-UHFFFAOYSA-N 8-methyl-7-propanoyl-11h-indolizino[1,2-b]quinolin-9-one Chemical class C1=CC=C2C=C(CN3C4=CC(=C(C3=O)C)C(=O)CC)C4=NC2=C1 QHTFEANXLNNBOX-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 17
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000007858 starting material Substances 0.000 description 6
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 5
- 229940127093 camptothecin Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- 102000003915 DNA Topoisomerases Human genes 0.000 description 2
- 108090000323 DNA Topoisomerases Proteins 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
- YPUWDDMFYRNEFX-UHFFFAOYSA-N 1-methoxy-2-[2-(2-methoxyethoxy)ethoxy]ethane Chemical compound COCCOCCOCCOC.COCCOCCOCCOC YPUWDDMFYRNEFX-UHFFFAOYSA-N 0.000 description 1
- HAWSQZCWOQZXHI-FQEVSTJZSA-N 10-Hydroxycamptothecin Chemical compound C1=C(O)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 HAWSQZCWOQZXHI-FQEVSTJZSA-N 0.000 description 1
- SEBNUFCVXMXPAE-UHFFFAOYSA-N 2h-indolizino[1,2-b]quinolin-1-one Chemical class C1=CC=CC2=C3N=C4C=CCC(=O)C4=CC3=CN21 SEBNUFCVXMXPAE-UHFFFAOYSA-N 0.000 description 1
- HAWSQZCWOQZXHI-UHFFFAOYSA-N CPT-OH Natural products C1=C(O)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 HAWSQZCWOQZXHI-UHFFFAOYSA-N 0.000 description 1
- 241000759909 Camptotheca Species 0.000 description 1
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000060390 Nothapodytes nimmoniana Species 0.000 description 1
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
- 102000007537 Type II DNA Topoisomerases Human genes 0.000 description 1
- 108010046308 Type II DNA Topoisomerases Proteins 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100001083 no cytotoxicity Toxicity 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7/589,848 | 1990-09-28 | ||
| US07/589,848 US5155225A (en) | 1990-09-28 | 1990-09-28 | Method for making certain pyrano[3',4':6,7]indolizino-[1,2-B]quinolinones |
| PCT/US1991/006869 WO1992006095A1 (en) | 1990-09-28 | 1991-09-23 | METHOD FOR MAKING CERTAIN PYRANO[3',4':6,7]INDOLIZINO[1,2-b]QUINOLINONES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR100192754B1 true KR100192754B1 (ko) | 1999-06-15 |
Family
ID=24359810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930700923A Expired - Fee Related KR100192754B1 (ko) | 1990-09-28 | 1991-09-23 | 특정 피라노(3',4':6,7)인돌리지노(1,2-b)퀴놀리논의 제조방법 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5155225A (https=) |
| EP (1) | EP0550621B1 (https=) |
| JP (1) | JP2534000B2 (https=) |
| KR (1) | KR100192754B1 (https=) |
| AT (1) | ATE173261T1 (https=) |
| AU (1) | AU653173B2 (https=) |
| CA (1) | CA2090966A1 (https=) |
| DE (1) | DE69130481T2 (https=) |
| DK (1) | DK0550621T3 (https=) |
| ES (1) | ES2123517T3 (https=) |
| GR (1) | GR3029356T3 (https=) |
| WO (1) | WO1992006095A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5552154A (en) * | 1989-11-06 | 1996-09-03 | The Stehlin Foundation For Cancer Research | Method for treating cancer with water-insoluble s-camptothecin of the closed lactone ring form and derivatives thereof |
| US5883255A (en) * | 1990-10-31 | 1999-03-16 | Smithkline Beecham Corporation | Substituted indolizino 1,2-b!quinolinones |
| US6080751A (en) * | 1992-01-14 | 2000-06-27 | The Stehlin Foundation For Cancer Research | Method for treating pancreatic cancer in humans with water-insoluble S-camptothecin of the closed lactone ring form and derivatives thereof |
| AU4288893A (en) * | 1992-04-17 | 1993-11-18 | Smithkline Beecham Corporation | Substituted indolizino(1,2-b)quinolinones |
| ZA936580B (en) * | 1992-09-08 | 1994-08-01 | Smithkline Beecham Corp | Process for preparing certain pyrrolo (3 4-b)quinolines certain 1H-pyrano(3' 4':6,7)indolizino(1 2-b)quinolin-3 14(4H 12H)-diones and certain 8-methyl-7-(oxopropyl)-idolizino(1 2-b)quinolin-9(11H)-ones |
| EP0835303A4 (en) * | 1995-06-07 | 2000-09-13 | Univ Jefferson | Anti-fungal agents and methods of identifying and using the same |
| US8349863B2 (en) * | 2005-10-10 | 2013-01-08 | Cipla Limited | Crystalline polymorphic form of a camptothecin analogue |
-
1990
- 1990-09-28 US US07/589,848 patent/US5155225A/en not_active Expired - Fee Related
-
1991
- 1991-09-23 JP JP3516076A patent/JP2534000B2/ja not_active Expired - Lifetime
- 1991-09-23 EP EP91917720A patent/EP0550621B1/en not_active Expired - Lifetime
- 1991-09-23 KR KR1019930700923A patent/KR100192754B1/ko not_active Expired - Fee Related
- 1991-09-23 AT AT91917720T patent/ATE173261T1/de not_active IP Right Cessation
- 1991-09-23 ES ES91917720T patent/ES2123517T3/es not_active Expired - Lifetime
- 1991-09-23 WO PCT/US1991/006869 patent/WO1992006095A1/en not_active Ceased
- 1991-09-23 DK DK91917720T patent/DK0550621T3/da active
- 1991-09-23 AU AU86398/91A patent/AU653173B2/en not_active Ceased
- 1991-09-23 DE DE69130481T patent/DE69130481T2/de not_active Expired - Fee Related
- 1991-09-23 CA CA002090966A patent/CA2090966A1/en not_active Abandoned
-
1999
- 1999-02-10 GR GR990400443T patent/GR3029356T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK0550621T3 (da) | 1999-07-26 |
| ES2123517T3 (es) | 1999-01-16 |
| GR3029356T3 (en) | 1999-05-28 |
| EP0550621B1 (en) | 1998-11-11 |
| JPH06501259A (ja) | 1994-02-10 |
| HK1012382A1 (en) | 1999-07-30 |
| DE69130481D1 (de) | 1998-12-17 |
| AU653173B2 (en) | 1994-09-22 |
| ATE173261T1 (de) | 1998-11-15 |
| EP0550621A4 (https=) | 1995-01-11 |
| JP2534000B2 (ja) | 1996-09-11 |
| DE69130481T2 (de) | 1999-06-24 |
| CA2090966A1 (en) | 1992-03-29 |
| AU8639891A (en) | 1992-04-28 |
| WO1992006095A1 (en) | 1992-04-16 |
| EP0550621A1 (en) | 1993-07-14 |
| US5155225A (en) | 1992-10-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wani et al. | Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogs | |
| KR100191193B1 (ko) | 6환 화합물 | |
| EP0737686B1 (en) | Camthothecin derivative with antitumor activity | |
| EP0074770A1 (en) | Camptothecin-1-oxide derivatives, process for preparing same, formulations comprising said derivatives and said derivatives for use in producing an anti-tumour effect | |
| KR100192754B1 (ko) | 특정 피라노(3',4':6,7)인돌리지노(1,2-b)퀴놀리논의 제조방법 | |
| Molina et al. | Iminophosphorane-mediated synthesis of the alkaloid cryptotackieine | |
| Johnson et al. | Emetic activity of reduced lysergamides | |
| Sánchez et al. | Two new β-carboline alkaloids from Aeschrion crenata | |
| FI67546C (fi) | Foerfarande foer framstaellning av vinkaminderivat | |
| CA1142176B (en) | 2-azaergolines and 2-aza-8 (or 9)-ergolenes | |
| CA1082179A (en) | Amide derivatives of vlb, leurosidine, leurocristine and related dimeric alkaloids | |
| Manna et al. | Synthesis of the alkaloid nauclefidin | |
| Ali et al. | Synthesis and reactions of 2, 3-dihydro-5-aryl-5h, 6h-thiazolo [3, 2-b]-2, 4-diazafluorene-3, 6-diones of potential biological activities | |
| Dumitrascu et al. | New pyrrolo [1, 2-a][1, 10] phenanthrolines with helical chirality | |
| HK1012382B (en) | Method for making certain pyrano 3',4':6,7]indolizino 1,2-b]quinolinones | |
| HU180725B (en) | Process for preparing dimeric derivatives of indole-dihydroindole-oxazolidinone-dione derivatives | |
| US4929730A (en) | Bis(1,2,5)thiadiazolo(3,4-b:3',4'-E) pyrazine, a process for the preparation thereof and a method of using same | |
| US20050159596A1 (en) | Cyclic compounds and their use as complex ligands | |
| HU193772B (en) | Process for producing new nitro-bis-indole derivatives | |
| US20050065338A1 (en) | Total synthesis of galanthamine, analogues and derivatives thereof | |
| EP1572696B1 (en) | Process for the direct preparation of 5-alkoxy and 5-acyloxy analogues of campthothecins or mappicene ketones | |
| Prasad et al. | Synthesis of 6H-[1]-Benzopyrano [3, 4-h]-1, 6-Naphthyridine-5, 7-Diones | |
| IE42132B1 (en) | Novel derivatives of vinblastine,vincristine and leurosidine | |
| Herbert | lTE PREPARATION OF PYRIW [4, 3.2-&] QUINAZOLINE AND PYRID0 [3.4, 5-&] QUINAZOLINE | |
| Barluenga et al. | Synthesis of halogenated hydrazone derivatives and their applicability in the preparation of 4‐chloropyrazoles |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19930326 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19960924 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19930326 Comment text: Patent Application |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19981029 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19990129 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 19990130 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| FPAY | Annual fee payment |
Payment date: 20020116 Year of fee payment: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20020116 Start annual number: 4 End annual number: 4 |
|
| LAPS | Lapse due to unpaid annual fee | ||
| PC1903 | Unpaid annual fee |
Termination category: Default of registration fee Termination date: 20031011 |