CA2090966A1 - Method for making certain pyrano¬3',4':6,7|indolizino¬1,2-b|quinolinones - Google Patents
Method for making certain pyrano¬3',4':6,7|indolizino¬1,2-b|quinolinonesInfo
- Publication number
- CA2090966A1 CA2090966A1 CA002090966A CA2090966A CA2090966A1 CA 2090966 A1 CA2090966 A1 CA 2090966A1 CA 002090966 A CA002090966 A CA 002090966A CA 2090966 A CA2090966 A CA 2090966A CA 2090966 A1 CA2090966 A1 CA 2090966A1
- Authority
- CA
- Canada
- Prior art keywords
- indolizino
- quinolin
- pyrano
- quinolinones
- reaction
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- 229930185107 quinolinone Natural products 0.000 title description 2
- 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 claims 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 claims abstract 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229940127093 camptothecin Drugs 0.000 description 6
- 239000007858 starting material 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
- 231100000433 cytotoxic Toxicity 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 102000003915 DNA Topoisomerases Human genes 0.000 description 2
- 108090000323 DNA Topoisomerases Proteins 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 239000000039 congener Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- 241000759909 Camptotheca Species 0.000 description 1
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 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
- 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
- 230000015556 catabolic process Effects 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 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
- 238000000825 ultraviolet detection Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US589,848 | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2090966A1 true CA2090966A1 (en) | 1992-03-29 |
Family
ID=24359810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002090966A Abandoned CA2090966A1 (en) | 1990-09-28 | 1991-09-23 | Method for making certain pyrano¬3',4':6,7|indolizino¬1,2-b|quinolinones |
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 |
| KR100192754B1 (ko) | 1999-06-15 |
| 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 |
| AU8639891A (en) | 1992-04-28 |
| WO1992006095A1 (en) | 1992-04-16 |
| EP0550621A1 (en) | 1993-07-14 |
| US5155225A (en) | 1992-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |