JP2008531487A5 - - Google Patents
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- JP2008531487A5 JP2008531487A5 JP2007555511A JP2007555511A JP2008531487A5 JP 2008531487 A5 JP2008531487 A5 JP 2008531487A5 JP 2007555511 A JP2007555511 A JP 2007555511A JP 2007555511 A JP2007555511 A JP 2007555511A JP 2008531487 A5 JP2008531487 A5 JP 2008531487A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl
- reaction
- converted
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 99
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- -1 (C 1 -C 6) - alkyl formamide Chemical compound 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 244000005894 Albizia lebbeck Species 0.000 claims description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005695 Ammonium acetate Substances 0.000 claims description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229940043376 ammonium acetate Drugs 0.000 claims description 2
- 235000019257 ammonium acetate Nutrition 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 6
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 3
- 235000011056 potassium acetate Nutrition 0.000 claims 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 238000007257 deesterification reaction Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003333 secondary alcohols Chemical class 0.000 claims 2
- 150000003512 tertiary amines Chemical class 0.000 claims 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- BUXBOOPDBDMDFZ-UHFFFAOYSA-N 4-ethyl-4-hydroxy-1,7-dihydropyrano[3,4-c]pyridine-3,8-dione Chemical compound C1=CNC(=O)C2=C1C(CC)(O)C(=O)OC2 BUXBOOPDBDMDFZ-UHFFFAOYSA-N 0.000 description 4
- 0 CC[C@@](C(C=C1N2Cc3c(*)c(c(*)c(*)c(C)c4*)c4nc13)=C(CO1)C2=O)(C1=O)O Chemical compound CC[C@@](C(C=C1N2Cc3c(*)c(c(*)c(*)c(C)c4*)c4nc13)=C(CO1)C2=O)(C1=O)O 0.000 description 4
- 239000012043 crude product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BUXBOOPDBDMDFZ-JTQLQIEISA-N (4s)-4-ethyl-4-hydroxy-1,7-dihydropyrano[3,4-c]pyridine-3,8-dione Chemical compound C1=CNC(=O)C2=C1[C@](CC)(O)C(=O)OC2 BUXBOOPDBDMDFZ-JTQLQIEISA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NPAAFPODGAKMTC-SANMLTNESA-N CCCCCN(C=N1)c2c(CN(C3=CC([C@]4(CC)O)=C5COC4=O)C5=O)c3nc3c2c1ccc3 Chemical compound CCCCCN(C=N1)c2c(CN(C3=CC([C@]4(CC)O)=C5COC4=O)C5=O)c3nc3c2c1ccc3 NPAAFPODGAKMTC-SANMLTNESA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- HDITUCONWLWUJR-UHFFFAOYSA-N diethylazanium;chloride Chemical compound [Cl-].CC[NH2+]CC HDITUCONWLWUJR-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05101338.1 | 2005-02-22 | ||
| EP05101338 | 2005-02-22 | ||
| PCT/EP2006/001306 WO2006089657A1 (en) | 2005-02-22 | 2006-02-14 | New synthesis of a camptothecin subunit |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008531487A JP2008531487A (ja) | 2008-08-14 |
| JP2008531487A5 true JP2008531487A5 (enExample) | 2011-03-17 |
| JP4861340B2 JP4861340B2 (ja) | 2012-01-25 |
Family
ID=36177738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007555511A Expired - Fee Related JP4861340B2 (ja) | 2005-02-22 | 2006-02-14 | カンプトセシンサブユニットの新規の合成法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7423152B2 (enExample) |
| EP (1) | EP1856124B1 (enExample) |
| JP (1) | JP4861340B2 (enExample) |
| KR (1) | KR100916175B1 (enExample) |
| CN (1) | CN101128467B (enExample) |
| AT (1) | ATE531719T1 (enExample) |
| CA (1) | CA2597388A1 (enExample) |
| IL (1) | IL185015A (enExample) |
| MX (1) | MX2007010033A (enExample) |
| TW (1) | TWI314932B (enExample) |
| WO (1) | WO2006089657A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7632540B2 (en) * | 2003-07-01 | 2009-12-15 | Transitions Optical, Inc. | Alignment facilities for optical dyes |
| CN104277144A (zh) * | 2008-07-31 | 2015-01-14 | 卢布里佐尔公司 | 共聚物及其润滑组合物 |
| CN101544651B (zh) * | 2009-04-24 | 2011-11-02 | 华东师范大学 | 多取代吡啶酮化合物的合成方法 |
| CN101591342B (zh) * | 2009-07-03 | 2011-07-27 | 华东师范大学 | 用于喜树碱类化合物制备的关键中间体合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5162532A (en) * | 1990-12-20 | 1992-11-10 | North Carolina State University | Intermediates and method of making camptothecin and camptothecin analogs |
| US5491237A (en) * | 1994-05-03 | 1996-02-13 | Glaxo Wellcome Inc. | Intermediates in pharmaceutical camptothecin preparation |
-
2006
- 2006-02-14 MX MX2007010033A patent/MX2007010033A/es active IP Right Grant
- 2006-02-14 KR KR1020077019083A patent/KR100916175B1/ko not_active Expired - Fee Related
- 2006-02-14 JP JP2007555511A patent/JP4861340B2/ja not_active Expired - Fee Related
- 2006-02-14 WO PCT/EP2006/001306 patent/WO2006089657A1/en not_active Ceased
- 2006-02-14 EP EP06706913A patent/EP1856124B1/en not_active Not-in-force
- 2006-02-14 AT AT06706913T patent/ATE531719T1/de active
- 2006-02-14 CN CN2006800056195A patent/CN101128467B/zh not_active Expired - Fee Related
- 2006-02-14 CA CA002597388A patent/CA2597388A1/en not_active Abandoned
- 2006-02-17 US US11/357,273 patent/US7423152B2/en not_active Expired - Fee Related
- 2006-02-20 TW TW095105638A patent/TWI314932B/zh not_active IP Right Cessation
-
2007
- 2007-08-02 IL IL185015A patent/IL185015A/en not_active IP Right Cessation
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