DE2310741A1 - Vincaminsaeureamide - Google Patents
VincaminsaeureamideInfo
- Publication number
- DE2310741A1 DE2310741A1 DE19732310741 DE2310741A DE2310741A1 DE 2310741 A1 DE2310741 A1 DE 2310741A1 DE 19732310741 DE19732310741 DE 19732310741 DE 2310741 A DE2310741 A DE 2310741A DE 2310741 A1 DE2310741 A1 DE 2310741A1
- Authority
- DE
- Germany
- Prior art keywords
- coupling
- vincamic
- vincamic acid
- acid
- hydrogen atom
- 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.)
- Pending
Links
- 150000001408 amides Chemical class 0.000 title claims description 7
- 238000010168 coupling process Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000003213 activating effect Effects 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 3
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 2
- 238000007098 aminolysis reaction Methods 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000010647 peptide synthesis reaction Methods 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- SMGLHFBQMBVRCP-UHFFFAOYSA-N 3-hydroxypropanamide Chemical compound NC(=O)CCO SMGLHFBQMBVRCP-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 6
- -1 alkyl radical Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 3
- 229960002726 vincamine Drugs 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JSLDLCGKZDUQSH-RTBUJCADSA-N 19-epivindolinine Natural products O=C(OC)[C@H]1[C@@]23[C@H](C)[C@]4([C@@H]5N(CC=C4)CC[C@]25c2c(N3)cccc2)C1 JSLDLCGKZDUQSH-RTBUJCADSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KILNDJCLJBOWAN-UHFFFAOYSA-N Tabersonine Natural products CCC12CC(=C3N(C)c4cc(OC)ccc4C35CCN(CC=C1)C25)C(=O)OC KILNDJCLJBOWAN-UHFFFAOYSA-N 0.000 description 1
- UXMCFEBDJVHVNH-HOJAQTOUSA-N ac1l52id Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(O)=O)N5C2=C1 UXMCFEBDJVHVNH-HOJAQTOUSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- KEVJSTPJPFMPNL-UHFFFAOYSA-N chloromethane;cyclohexane Chemical compound ClC.C1CCCCC1 KEVJSTPJPFMPNL-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- FNGGIPWAZSFKCN-ACRUOGEOSA-N tabersonine Chemical compound N1C2=CC=CC=C2[C@]2([C@H]34)C1=C(C(=O)OC)C[C@]3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-ACRUOGEOSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- FNGGIPWAZSFKCN-UHFFFAOYSA-N xi-tabersonine Natural products N1C2=CC=CC=C2C2(C34)C1=C(C(=O)OC)CC3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE780257A BE780257A (fr) | 1972-03-06 | 1972-03-06 | Amides de l'acide vincaminique. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2310741A1 true DE2310741A1 (de) | 1973-09-20 |
Family
ID=3859365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732310741 Pending DE2310741A1 (de) | 1972-03-06 | 1973-03-03 | Vincaminsaeureamide |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS48103599A (enrdf_load_stackoverflow) |
| BE (1) | BE780257A (enrdf_load_stackoverflow) |
| DE (1) | DE2310741A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2175040A1 (enrdf_load_stackoverflow) |
| HU (1) | HU167353B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114249721B (zh) * | 2021-11-29 | 2023-10-17 | 南京中医药大学 | 长春胺peg衍生物与在制备治疗糖尿病周围神经病变、糖尿病足及肺纤维化药物中的应用 |
-
1972
- 1972-03-06 BE BE780257A patent/BE780257A/xx unknown
-
1973
- 1973-03-03 DE DE19732310741 patent/DE2310741A1/de active Pending
- 1973-03-05 FR FR7307802A patent/FR2175040A1/fr not_active Withdrawn
- 1973-03-06 HU HUOI000158 patent/HU167353B/hu unknown
- 1973-03-06 JP JP2577673A patent/JPS48103599A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS48103599A (enrdf_load_stackoverflow) | 1973-12-25 |
| HU167353B (enrdf_load_stackoverflow) | 1975-09-27 |
| BE780257A (fr) | 1972-07-03 |
| FR2175040A1 (en) | 1973-10-19 |
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