GB1457069A - Process for the prepataion of n-formyl diindole alkaloids - Google Patents
Process for the prepataion of n-formyl diindole alkaloidsInfo
- Publication number
- GB1457069A GB1457069A GB5496474A GB5496474A GB1457069A GB 1457069 A GB1457069 A GB 1457069A GB 5496474 A GB5496474 A GB 5496474A GB 5496474 A GB5496474 A GB 5496474A GB 1457069 A GB1457069 A GB 1457069A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formyl
- diindole
- alkaloids
- dec
- leurosine
- 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
Links
- 229930013930 alkaloid Natural products 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- DXGTUUQHTDOFFQ-UHFFFAOYSA-N [N].C1=CC=C2NC=CC2=C1 Chemical group [N].C1=CC=C2NC=CC2=C1 DXGTUUQHTDOFFQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- LPGWZGMPDKDHEP-HLTPFJCJSA-N Leurosine Chemical compound C([C@]1([C@@H]2O1)CC)N(CCC=1C3=CC=CC=C3NC=11)C[C@H]2C[C@]1(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC LPGWZGMPDKDHEP-HLTPFJCJSA-N 0.000 abstract 1
- LPGWZGMPDKDHEP-GKWAKPNHSA-N Leurosine 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@]6(CC)O[C@@H]6[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C LPGWZGMPDKDHEP-GKWAKPNHSA-N 0.000 abstract 1
- 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 abstract 1
- 150000003797 alkaloid derivatives Chemical class 0.000 abstract 1
- 239000003849 aromatic solvent Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- GLDSBTCHEGZWCV-HLTPFJCJSA-N leuroformine Chemical compound C([C@]1([C@@H]2O1)CC)N(CCC=1C3=CC=CC=C3NC=11)C[C@H]2C[C@]1(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C=O)=C2C=C1OC GLDSBTCHEGZWCV-HLTPFJCJSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 230000000737 periodic effect Effects 0.000 abstract 1
- 229960003048 vinblastine Drugs 0.000 abstract 1
- 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 abstract 1
- 229960004528 vincristine Drugs 0.000 abstract 1
- 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 abstract 1
- 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 abstract 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 And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI531A HU168433B (enrdf_load_html_response) | 1973-12-20 | 1973-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1457069A true GB1457069A (en) | 1976-12-01 |
Family
ID=11000942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5496474A Expired GB1457069A (en) | 1973-12-20 | 1974-12-19 | Process for the prepataion of n-formyl diindole alkaloids |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5095300A (enrdf_load_html_response) |
| AT (1) | AT335077B (enrdf_load_html_response) |
| BE (1) | BE823560A (enrdf_load_html_response) |
| DD (1) | DD116042A5 (enrdf_load_html_response) |
| GB (1) | GB1457069A (enrdf_load_html_response) |
| HU (1) | HU168433B (enrdf_load_html_response) |
| IL (1) | IL46286A0 (enrdf_load_html_response) |
| RO (1) | RO63736A (enrdf_load_html_response) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037290B1 (en) * | 1980-04-02 | 1984-03-21 | Eli Lilly And Company | Process for preparing a vinca dimer |
| EP0037289B1 (en) * | 1980-04-02 | 1984-08-01 | Eli Lilly And Company | Method of preparing a vinca dimer |
-
1973
- 1973-12-20 HU HURI531A patent/HU168433B/hu unknown
-
1974
- 1974-12-17 AT AT1005074A patent/AT335077B/de active
- 1974-12-18 IL IL46286A patent/IL46286A0/xx unknown
- 1974-12-18 DD DD183160A patent/DD116042A5/xx unknown
- 1974-12-19 BE BE151682A patent/BE823560A/xx unknown
- 1974-12-19 RO RO7400080859A patent/RO63736A/ro unknown
- 1974-12-19 JP JP49145092A patent/JPS5095300A/ja active Pending
- 1974-12-19 GB GB5496474A patent/GB1457069A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037290B1 (en) * | 1980-04-02 | 1984-03-21 | Eli Lilly And Company | Process for preparing a vinca dimer |
| EP0037289B1 (en) * | 1980-04-02 | 1984-08-01 | Eli Lilly And Company | Method of preparing a vinca dimer |
Also Published As
| Publication number | Publication date |
|---|---|
| AT335077B (de) | 1977-02-25 |
| RO63736A (fr) | 1978-10-15 |
| JPS5095300A (enrdf_load_html_response) | 1975-07-29 |
| IL46286A0 (en) | 1975-03-13 |
| ATA1005074A (de) | 1976-06-15 |
| DD116042A5 (enrdf_load_html_response) | 1975-11-05 |
| BE823560A (fr) | 1975-04-16 |
| HU168433B (enrdf_load_html_response) | 1976-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |