KR950702987A - 특정 피롤로[3,4-b] 퀴놀린, 특정 1H-피라노[3′,4′: 6,7]인돌리지노[1,2-b] 퀴놀린-3,14(4H,12H)-디온, 및 특정 8-메틸-7-(옥소프로필)-인돌리지노[1,2-b] 퀴놀린-9-(11H)-온을 제조하는 방법(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)-INDOLIZINO[1,2-b]QUINOLIN-9(11H)-ONES - Google Patents
특정 피롤로[3,4-b] 퀴놀린, 특정 1H-피라노[3′,4′: 6,7]인돌리지노[1,2-b] 퀴놀린-3,14(4H,12H)-디온, 및 특정 8-메틸-7-(옥소프로필)-인돌리지노[1,2-b] 퀴놀린-9-(11H)-온을 제조하는 방법(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)-INDOLIZINO[1,2-b]QUINOLIN-9(11H)-ONESInfo
- Publication number
- KR950702987A KR950702987A KR1019950700883A KR19950700883A KR950702987A KR 950702987 A KR950702987 A KR 950702987A KR 1019950700883 A KR1019950700883 A KR 1019950700883A KR 19950700883 A KR19950700883 A KR 19950700883A KR 950702987 A KR950702987 A KR 950702987A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen
- quinolin
- quinoline
- indolizino
- group
- 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.)
- Withdrawn
Links
- WAZSVCKLDOMJJX-UHFFFAOYSA-N 2h-pyrrolo[3,4-b]quinoline Chemical compound C1=CC=CC2=CC3=CNC=C3N=C21 WAZSVCKLDOMJJX-UHFFFAOYSA-N 0.000 title claims 5
- SNNLGDCYCOKWFN-UHFFFAOYSA-N C1=CC=C2C=C(CN3C4=CC=5CC(OCC=5C3=O)=O)C4=NC2=C1 Chemical compound C1=CC=C2C=C(CN3C4=CC=5CC(OCC=5C3=O)=O)C4=NC2=C1 SNNLGDCYCOKWFN-UHFFFAOYSA-N 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title claims 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
- 150000003248 quinolines Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 37
- 239000001257 hydrogen Substances 0.000 claims abstract 34
- 238000000034 method Methods 0.000 claims abstract 32
- 150000002431 hydrogen Chemical class 0.000 claims abstract 21
- 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 claims abstract 20
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 11
- 150000002596 lactones Chemical class 0.000 claims abstract 9
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical class O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims abstract 9
- 125000000524 functional group Chemical group 0.000 claims abstract 8
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims abstract 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract 6
- MWFNDFNHIBULHZ-UHFFFAOYSA-N oxoaluminum;hydrochloride Chemical compound Cl.[Al]=O MWFNDFNHIBULHZ-UHFFFAOYSA-N 0.000 claims abstract 6
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims abstract 5
- 229940127093 camptothecin Drugs 0.000 claims abstract 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract 5
- 150000004820 halides Chemical class 0.000 claims abstract 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims abstract 5
- 125000003277 amino group Chemical group 0.000 claims abstract 4
- 150000002148 esters Chemical group 0.000 claims abstract 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 4
- 150000002576 ketones Chemical class 0.000 claims abstract 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims abstract 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract 4
- 238000007115 1,4-cycloaddition reaction Methods 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 27
- -1 imidate ester Chemical class 0.000 claims 20
- 239000002798 polar solvent Substances 0.000 claims 12
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims 12
- 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 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- 239000003795 chemical substances by application Substances 0.000 claims 8
- 239000002168 alkylating agent Substances 0.000 claims 6
- 229940100198 alkylating agent Drugs 0.000 claims 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 6
- 150000003949 imides Chemical class 0.000 claims 6
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 6
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 6
- 229960000303 topotecan Drugs 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 150000002465 imidoyl halides Chemical class 0.000 claims 5
- 238000007363 ring formation reaction Methods 0.000 claims 5
- KLFJSYOEEYWQMR-NRFANRHFSA-N 10-methoxycamptothecin Chemical compound C1=C(OC)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 KLFJSYOEEYWQMR-NRFANRHFSA-N 0.000 claims 4
- 230000018044 dehydration Effects 0.000 claims 4
- 238000006297 dehydration reaction Methods 0.000 claims 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 3
- SEZHLKZEWYFCRB-UHFFFAOYSA-N 1,2-dimethoxyethane;oxolane Chemical compound C1CCOC1.COCCOC SEZHLKZEWYFCRB-UHFFFAOYSA-N 0.000 claims 3
- BCMGEDGPGRHWES-UHFFFAOYSA-N 3-(8-methyl-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl)propanal Chemical compound C1=CC=C2C=C(CN3C4=CC(CCC=O)=C(C3=O)C)C4=NC2=C1 BCMGEDGPGRHWES-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 150000005690 diesters Chemical class 0.000 claims 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 238000010992 reflux Methods 0.000 claims 3
- 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 claims 2
- FBGCJOHMGWZUII-UHFFFAOYSA-N 19-ethyl-7-methoxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione Chemical compound C1=C(OC)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5CC)C4=NC2=C1 FBGCJOHMGWZUII-UHFFFAOYSA-N 0.000 claims 2
- XVMZDZFTCKLZTF-UHFFFAOYSA-N 9-methoxycamtothecin Natural products C1=CC(OC)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 XVMZDZFTCKLZTF-UHFFFAOYSA-N 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- HDLGLUQWHLIHQA-UHFFFAOYSA-N CCCC1=C2C=C3CN4C(=C3NC2=CC=C1)CC=C(C4=O)C(=O)OC Chemical compound CCCC1=C2C=C3CN4C(=C3NC2=CC=C1)CC=C(C4=O)C(=O)OC HDLGLUQWHLIHQA-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- KLFJSYOEEYWQMR-UHFFFAOYSA-N CPT-OMe Natural products C1=C(OC)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 KLFJSYOEEYWQMR-UHFFFAOYSA-N 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 150000002085 enols Chemical class 0.000 claims 2
- VDDXQSUSMHZCLS-UHFFFAOYSA-N ethenyl trifluoromethanesulfonate Chemical class FC(F)(F)S(=O)(=O)OC=C VDDXQSUSMHZCLS-UHFFFAOYSA-N 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 150000002463 imidates Chemical class 0.000 claims 2
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 2
- 229960004768 irinotecan Drugs 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- IEEHKTFVUIVORU-UHFFFAOYSA-N 2-methylpropanedioyl dichloride Chemical compound ClC(=O)C(C)C(Cl)=O IEEHKTFVUIVORU-UHFFFAOYSA-N 0.000 claims 1
- OZIVLIFPJDZGOQ-UHFFFAOYSA-N 6,11-dihydro-5h-indolizino[1,2-b]quinolin-9-one Chemical group N1C2=CC=CC=C2C=C2C1=C1CC=CC(=O)N1C2 OZIVLIFPJDZGOQ-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000006352 cycloaddition reaction Methods 0.000 claims 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000010189 synthetic method Methods 0.000 claims 1
- 150000003509 tertiary alcohols Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94149692A | 1992-09-08 | 1992-09-08 | |
| US07/941496 | 1992-09-08 | ||
| PCT/US1993/008434 WO1994005672A1 (en) | 1992-09-08 | 1993-09-08 | 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)-INDOLIZINO[1,2-b]QUINOLIN-9(11H)-ONES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR950702987A true KR950702987A (ko) | 1995-08-23 |
Family
ID=25476581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950700883A Withdrawn KR950702987A (ko) | 1992-09-08 | 1993-09-08 | 특정 피롤로[3,4-b] 퀴놀린, 특정 1H-피라노[3′,4′: 6,7]인돌리지노[1,2-b] 퀴놀린-3,14(4H,12H)-디온, 및 특정 8-메틸-7-(옥소프로필)-인돌리지노[1,2-b] 퀴놀린-9-(11H)-온을 제조하는 방법(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)-INDOLIZINO[1,2-b]QUINOLIN-9(11H)-ONES |
Country Status (11)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6660861B1 (en) * | 2003-03-27 | 2003-12-09 | Council Of Scientific And Industrial Research | Process for preparing Topotecan from 10-hydroxy-4-(S) camptothecin |
| CN2757510Y (zh) | 2004-12-06 | 2006-02-08 | 鸿富锦精密工业（深圳）有限公司 | 散热器扣具 |
| US7520313B2 (en) | 2006-03-16 | 2009-04-21 | Fu Zhun Precision Industry (Shen Zhen) Co., Ltd. | Locking device for heat sink |
| CN105859716B (zh) * | 2016-05-06 | 2018-03-09 | 华东师范大学 | 一种合成喜树碱类化合物中5‑6并环结构的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5626677B2 (enrdf_load_html_response) * | 1973-03-26 | 1981-06-19 | ||
| JPS5217499A (en) * | 1975-07-31 | 1977-02-09 | Nippon Chemiphar Co Ltd | Preparation of mappicine |
| DE2534601C2 (de) * | 1975-08-02 | 1987-01-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Camptothecin und Camptothecin-Derivaten |
| CA1332413C (en) * | 1987-06-25 | 1994-10-11 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives and process for preparing same |
| JP2711728B2 (ja) * | 1989-08-29 | 1998-02-10 | 株式会社ヤクルト本社 | 新規キノリン誘導体およびその製造法 |
| US5155225A (en) * | 1990-09-28 | 1992-10-13 | Smithkline Beecham Corporation | Method for making certain pyrano[3',4':6,7]indolizino-[1,2-B]quinolinones |
-
1993
- 1993-09-07 ZA ZA936580A patent/ZA936580B/xx unknown
- 1993-09-08 WO PCT/US1993/008434 patent/WO1994005672A1/en not_active Application Discontinuation
- 1993-09-08 NZ NZ255942A patent/NZ255942A/en unknown
- 1993-09-08 AU AU51023/93A patent/AU5102393A/en not_active Abandoned
- 1993-09-08 MX MX9305517A patent/MX9305517A/es unknown
- 1993-09-08 CN CN93119287A patent/CN1096297A/zh active Pending
- 1993-09-08 EP EP93920496A patent/EP0660835A4/en not_active Withdrawn
- 1993-09-08 JP JP6507518A patent/JPH08501104A/ja active Pending
- 1993-09-08 CA CA002144048A patent/CA2144048A1/en not_active Abandoned
- 1993-09-08 KR KR1019950700883A patent/KR950702987A/ko not_active Withdrawn
- 1993-11-02 TW TW082109133A patent/TW246674B/zh active
-
1997
- 1997-07-11 AU AU28591/97A patent/AU2859197A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2859197A (en) | 1997-10-23 |
| EP0660835A1 (en) | 1995-07-05 |
| NZ255942A (en) | 1996-11-26 |
| ZA936580B (en) | 1994-08-01 |
| TW246674B (enrdf_load_html_response) | 1995-05-01 |
| JPH08501104A (ja) | 1996-02-06 |
| EP0660835A4 (en) | 1995-08-16 |
| WO1994005672A1 (en) | 1994-03-17 |
| CA2144048A1 (en) | 1994-03-17 |
| CN1096297A (zh) | 1994-12-14 |
| MX9305517A (es) | 1994-05-31 |
| AU5102393A (en) | 1994-03-29 |
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