JPH0613532B2 - 二量体の生成方法 - Google Patents

二量体の生成方法

Info

Publication number: JPH0613532B2
Authority: JP; Japan
Prior art keywords: formula; alkyl; alk; enamine; group
Prior art date: 1987-08-06
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 - Lifetime

Application number

JP63196999A

Other languages

English (en)

Japanese (ja)

Other versions

JPH01151590A (ja

Inventor

ジェイムズ・ピー・クートニー

ルイス・エス・エル・チョイ

潤中野

博樹塚本

カミール・エイ・ブーレット

マイケル・マキュー

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

YUNIBAASHITEI OBU BURITEITSUSHU KORONBIA ZA

Original Assignee

YUNIBAASHITEI OBU BURITEITSUSHU KORONBIA ZA

Priority date (The priority date 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 date listed.)

1987-08-06

Filing date

1988-08-06

Publication date

1994-02-23

1988-08-06 Application filed by YUNIBAASHITEI OBU BURITEITSUSHU KORONBIA ZA filed Critical YUNIBAASHITEI OBU BURITEITSUSHU KORONBIA ZA

1989-06-14 Publication of JPH01151590A publication Critical patent/JPH01151590A/ja

1994-02-23 Publication of JPH0613532B2 publication Critical patent/JPH0613532B2/ja

2009-02-23 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000539 dimer Substances 0.000 title claims description 11
150000002081 enamines Chemical class 0.000 claims description 52
238000000034 method Methods 0.000 claims description 48
150000002466 imines Chemical class 0.000 claims description 46
239000000047 product Substances 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 25
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 24
229960003048 vinblastine Drugs 0.000 claims description 22
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 22
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 20
238000007254 oxidation reaction Methods 0.000 claims description 20
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
230000003647 oxidation Effects 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 17
-1 1,4-dihydropyridine compound Chemical class 0.000 claims description 16
238000005273 aeration Methods 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
238000006213 oxygenation reaction Methods 0.000 claims description 14
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 11
150000002431 hydrogen Chemical group 0.000 claims description 11
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 11
LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical group C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 10
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 9
238000001704 evaporation Methods 0.000 claims description 8
125000001041 indolyl group Chemical group 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
229930013930 alkaloid Natural products 0.000 claims description 6
239000005515 coenzyme Substances 0.000 claims description 6
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
150000003797 alkaloid derivatives Chemical class 0.000 claims description 5
230000001590 oxidative effect Effects 0.000 claims description 5
125000000547 substituted alkyl group Chemical group 0.000 claims description 5
150000001204 N-oxides Chemical class 0.000 claims description 4
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
239000012346 acetyl chloride Substances 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
238000005580 one pot reaction Methods 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
238000003756 stirring Methods 0.000 claims description 4
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 4
229960004528 vincristine Drugs 0.000 claims description 4
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 3
229940122803 Vinca alkaloid Drugs 0.000 claims description 3
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
QUIJMHDIAFOPRK-UHFFFAOYSA-N 1-cyclooctylazocane Chemical group C1CCCCCCC1N1CCCCCCC1 QUIJMHDIAFOPRK-UHFFFAOYSA-N 0.000 claims description 2
241001661930 Aspidosperma Species 0.000 claims description 2
241001246918 Tabernanthe iboga Species 0.000 claims description 2
150000004075 acetic anhydrides Chemical class 0.000 claims description 2
239000003125 aqueous solvent Substances 0.000 claims description 2
238000003776 cleavage reaction Methods 0.000 claims description 2
239000012467 final product Substances 0.000 claims description 2
229910021645 metal ion Inorganic materials 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
HXIPLHBIHBQWGY-UHFFFAOYSA-N 2,3-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1CN=CC=C1 HXIPLHBIHBQWGY-UHFFFAOYSA-N 0.000 claims 1
230000005587 bubbling Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
239000000543 intermediate Substances 0.000 description 46
239000000243 solution Substances 0.000 description 30
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
239000012298 atmosphere Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
229910052786 argon Inorganic materials 0.000 description 12
239000003638 chemical reducing agent Substances 0.000 description 12
238000004007 reversed phase HPLC Methods 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
238000004458 analytical method Methods 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
GKWYINOZGDHWRA-UHFFFAOYSA-N catharanthine Natural products C1C(CC)(O)CC(CC2C(=O)OC)CN1CCC1=C2NC2=CC=CC=C12 GKWYINOZGDHWRA-UHFFFAOYSA-N 0.000 description 8
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 7
230000000694 effects Effects 0.000 description 7
229960003966 nicotinamide Drugs 0.000 description 7
239000011570 nicotinamide Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
CXBGOBGJHGGWIE-IYJDUVQVSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-IYJDUVQVSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
WVTGEXAIVZDLCR-UHFFFAOYSA-N Vindoline Natural products CC1C2CN3CCCC14CCC5Nc6ccccc6C25C34 WVTGEXAIVZDLCR-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
CMKFQVZJOWHHDV-DYHNYNMBSA-N catharanthine Chemical compound C([C@@H]1C=C([C@@H]2[C@@]3(C1)C(=O)OC)CC)N2CCC1=C3NC2=CC=CC=C12 CMKFQVZJOWHHDV-DYHNYNMBSA-N 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000007942 carboxylates Chemical group 0.000 description 3
239000012043 crude product Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 2
KGUMNRYFUFLBGA-UHFFFAOYSA-N 1,4-dihydropyridine-3-carboxamide Chemical class NC(=O)C1=CNC=CC1 KGUMNRYFUFLBGA-UHFFFAOYSA-N 0.000 description 2
JXLYSJRDGCGARV-PJXZDTQASA-N Leurosidine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-PJXZDTQASA-N 0.000 description 2
241001274216 Naso Species 0.000 description 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
JXLYSJRDGCGARV-KSNABSRWSA-N ac1l29ym Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-KSNABSRWSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
238000007865 diluting Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
238000011002 quantification Methods 0.000 description 2
JIJVOHRWYUICGU-UHFFFAOYSA-N 1-benzhydryl-4h-pyridine-3-carboxamide Chemical compound C1=CCC(C(=O)N)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 JIJVOHRWYUICGU-UHFFFAOYSA-N 0.000 description 1
WJNYVKCAEHASOF-UHFFFAOYSA-N 1-benzyl-4h-pyridine-3-carbonitrile Chemical compound C1=CCC(C#N)=CN1CC1=CC=CC=C1 WJNYVKCAEHASOF-UHFFFAOYSA-N 0.000 description 1
QSXXRQOSDOIGIV-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;(2,2,2-trifluoroacetyl) 2,2,2-trifluoroacetate Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)OC(=O)C(F)(F)F QSXXRQOSDOIGIV-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
UEZNSCCMEMUEMO-UHFFFAOYSA-N 6-chloro-9-methylpurine Chemical compound N1=CN=C2N(C)C=NC2=C1Cl UEZNSCCMEMUEMO-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000208328 Catharanthus Species 0.000 description 1
101100134922 Gallus gallus COR5 gene Proteins 0.000 description 1
239000007987 MES buffer Substances 0.000 description 1
LXAOWPZJTWFMLM-UHFFFAOYSA-N NC(C(CCC1)N1NCC1=CNC=CC1)=O Chemical compound NC(C(CCC1)N1NCC1=CNC=CC1)=O LXAOWPZJTWFMLM-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000863480 Vinca Species 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000000719 anti-leukaemic effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
235000005152 nicotinamide Nutrition 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229960005326 pyrithyldione Drugs 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000003643 water by type Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

JP63196999A 1987-08-06 1988-08-06 二量体の生成方法 Expired - Lifetime JPH0613532B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA000543832A CA1341262C (en)	1987-08-06	1987-08-06	A new process of the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine
CA543,832		1987-08-06

Publications (2)

Publication Number	Publication Date
JPH01151590A JPH01151590A (ja)	1989-06-14
JPH0613532B2 true JPH0613532B2 (ja)	1994-02-23

Family

ID=4136214

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63196999A Expired - Lifetime JPH0613532B2 (ja)	1987-08-06	1988-08-06	二量体の生成方法

Country Status (12)

Country	Link
JP (1)	JPH0613532B2 (da)
AU (1)	AU617342B2 (da)
BE (1)	BE1003228A4 (da)
CA (1)	CA1341262C (da)
CH (1)	CH676711A5 (da)
DE (1)	DE3826412A1 (da)
GB (1)	GB2215331B (da)
HU (1)	HU208829B (da)
IT (1)	IT1227155B (da)
NL (1)	NL8801966A (da)
SE (1)	SE467875B (da)
ZA (1)	ZA885765B (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3010151U (ja) *	1994-04-26	1995-04-25	スミ子片山	切込みのついた筒形食器収納ケース。

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5047528A (en) *	1987-01-22	1991-09-10	University Of Bristish Columbia	Process of synthesis of vinblastine and vincristine
USRE37449E1 (en)	1987-02-06	2001-11-13	University Of British Columbia	Process of synthesis of 3′,4′-anhydrovinblastine, vinblastine and vincristine
US5432279A (en) *	1989-03-04	1995-07-11	Mitsui Petrochemical Industries, Inc.	Process for the preparation of binary indole alkaloids
CA2056799C (en) *	1990-11-30	2002-01-01	Hiroshi Ikawa	1,4-dihydropyridine derivatives and methods of producing the same
FR2779146B1 (fr) *	1998-06-02	2002-01-18	Roowin	Nouveaux derives de vinca-alcaloides et procedes de preparation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4279817A (en) *	1975-05-30	1981-07-21	The United States Of America As Represented By The Department Of Health & Human Services	Method for producing dimer alkaloids
HU195513B (en) *	1984-10-16	1988-05-30	Richter Gedeon Vegyeszet	Process for producing stable solutions of alkaloides with bis-indole skeleton
AU590873B2 (en) *	1985-03-12	1989-11-23	University Of Vermont And State Agricultural College, The	Synthesis of vinblastine and vincristine type compounds
CA1341261C (en) *	1987-01-22	2001-06-26	James P. Kutney	Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine

1987
- 1987-08-06 CA CA000543832A patent/CA1341262C/en not_active Expired - Fee Related
1988
- 1988-08-03 SE SE8802813A patent/SE467875B/sv not_active IP Right Cessation
- 1988-08-03 DE DE3826412A patent/DE3826412A1/de not_active Ceased
- 1988-08-05 CH CH2974/88A patent/CH676711A5/de not_active IP Right Cessation
- 1988-08-05 IT IT8821678A patent/IT1227155B/it active
- 1988-08-05 BE BE8800908A patent/BE1003228A4/fr not_active IP Right Cessation
- 1988-08-05 NL NL8801966A patent/NL8801966A/nl not_active Application Discontinuation
- 1988-08-05 ZA ZA885765A patent/ZA885765B/xx unknown
- 1988-08-05 AU AU20512/88A patent/AU617342B2/en not_active Ceased
- 1988-08-06 JP JP63196999A patent/JPH0613532B2/ja not_active Expired - Lifetime
- 1988-08-08 GB GB8818765A patent/GB2215331B/en not_active Expired - Lifetime
- 1988-08-08 HU HU884126A patent/HU208829B/hu not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3010151U (ja) *	1994-04-26	1995-04-25	スミ子片山	切込みのついた筒形食器収納ケース。

Also Published As

Publication number	Publication date
CH676711A5 (da)	1991-02-28
GB8818765D0 (en)	1988-09-07
NL8801966A (nl)	1989-03-01
AU2051288A (en)	1989-02-09
HU208829B (en)	1994-01-28
IT1227155B (it)	1991-03-19
SE8802813D0 (sv)	1988-08-03
HUT50351A (en)	1990-01-29
GB2215331B (en)	1992-01-02
SE8802813L (sv)	1989-02-07
BE1003228A4 (fr)	1992-02-04
ZA885765B (en)	1989-09-27
IT8821678A0 (it)	1988-08-05
JPH01151590A (ja)	1989-06-14
DE3826412A1 (de)	1989-02-16
GB2215331A (en)	1989-09-20
SE467875B (sv)	1992-09-28
AU617342B2 (en)	1991-11-28
CA1341262C (en)	2001-06-26

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Ferroud et al.	2001	A singlet oxygen mediated new access to hydroxyindolenine-catharanthine derivatives by two sequential oxidations

JPH0613532B2 - 二量体の生成方法 - Google Patents

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