IE38310B1 - Novel 1,2,3,4-tetrahydro-9h-pyrido (3,4,6) indole derivatitves and their use as intermediates in the synthesis of eburnamonine - Google Patents
Novel 1,2,3,4-tetrahydro-9h-pyrido (3,4,6) indole derivatitves and their use as intermediates in the synthesis of eburnamonineInfo
- Publication number
- IE38310B1 IE38310B1 IE1307/73A IE130773A IE38310B1 IE 38310 B1 IE38310 B1 IE 38310B1 IE 1307/73 A IE1307/73 A IE 1307/73A IE 130773 A IE130773 A IE 130773A IE 38310 B1 IE38310 B1 IE 38310B1
- Authority
- IE
- Ireland
- Prior art keywords
- indole
- pyrido
- tetrahydro
- alkyloxy
- preparation
- Prior art date
Links
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 2
- WYJAPUKIYAZSEM-MOPGFXCFSA-N Eburnamonine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)CC(=O)N5C2=C1 WYJAPUKIYAZSEM-MOPGFXCFSA-N 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 229950011119 eburnamonine Drugs 0.000 title 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- WYJAPUKIYAZSEM-UHFFFAOYSA-N rac-Eburnamonin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(=O)N5C2=C1 WYJAPUKIYAZSEM-UHFFFAOYSA-N 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 abstract 3
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 abstract 2
- CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical class N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 229930013930 alkaloid Natural products 0.000 abstract 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002475 indoles Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7227501A FR2194193A5 (en, 2012) | 1972-07-31 | 1972-07-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE38310L IE38310L (en) | 1974-01-31 |
| IE38310B1 true IE38310B1 (en) | 1978-02-15 |
Family
ID=9102588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1307/73A IE38310B1 (en) | 1972-07-31 | 1973-07-31 | Novel 1,2,3,4-tetrahydro-9h-pyrido (3,4,6) indole derivatitves and their use as intermediates in the synthesis of eburnamonine |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3862160A (en, 2012) |
| JP (1) | JPS573676B2 (en, 2012) |
| BE (1) | BE802913A (en, 2012) |
| CA (1) | CA1013747A (en, 2012) |
| CH (1) | CH572926A5 (en, 2012) |
| DE (1) | DE2338838A1 (en, 2012) |
| DK (1) | DK138454B (en, 2012) |
| FR (1) | FR2194193A5 (en, 2012) |
| GB (1) | GB1390304A (en, 2012) |
| HU (1) | HU166483B (en, 2012) |
| IE (1) | IE38310B1 (en, 2012) |
| NL (1) | NL183824C (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU187139B (en) * | 1982-06-30 | 1985-11-28 | Richter Gedeon Vegyeszet | Process for preparing new eburnan derivatives |
| JPS62134883U (en, 2012) * | 1986-02-18 | 1987-08-25 | ||
| JPH0323093U (en, 2012) * | 1989-07-12 | 1991-03-11 | ||
| US5244905A (en) * | 1990-08-31 | 1993-09-14 | Warner-Lambert Company | N-substituted cycloalkyl and polycycloalkyl polyhydro-β-carboline-phenylalanine- and phenethylamine derivatives |
| CN107417595B (zh) * | 2017-03-27 | 2020-07-24 | 四川大学 | 一种基于自由基串联反应的系列单萜吲哚生物碱骨架及天然产物的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029247A (en) * | 1960-07-28 | 1962-04-10 | Miles Lab | Certain tetrahydro-beta-carbolines |
-
1972
- 1972-07-31 FR FR7227501A patent/FR2194193A5/fr not_active Expired
-
1973
- 1973-07-17 CH CH1041373A patent/CH572926A5/xx not_active IP Right Cessation
- 1973-07-24 US US382061A patent/US3862160A/en not_active Expired - Lifetime
- 1973-07-27 BE BE133974A patent/BE802913A/xx not_active IP Right Cessation
- 1973-07-30 CA CA177,628A patent/CA1013747A/fr not_active Expired
- 1973-07-30 HU HURO741A patent/HU166483B/hu not_active IP Right Cessation
- 1973-07-31 NL NLAANVRAGE7310608,A patent/NL183824C/xx not_active IP Right Cessation
- 1973-07-31 DE DE19732338838 patent/DE2338838A1/de not_active Ceased
- 1973-07-31 GB GB3639273A patent/GB1390304A/en not_active Expired
- 1973-07-31 JP JP8555873A patent/JPS573676B2/ja not_active Expired
- 1973-07-31 DK DK419573AA patent/DK138454B/da not_active IP Right Cessation
- 1973-07-31 IE IE1307/73A patent/IE38310B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU166483B (en, 2012) | 1975-03-28 |
| NL183824C (nl) | 1989-02-01 |
| NL7310608A (en, 2012) | 1974-02-04 |
| US3862160A (en) | 1975-01-21 |
| JPS573676B2 (en, 2012) | 1982-01-22 |
| BE802913A (fr) | 1974-01-28 |
| DE2338838A1 (de) | 1974-02-14 |
| NL183824B (nl) | 1988-09-01 |
| CH572926A5 (en, 2012) | 1976-02-27 |
| GB1390304A (en) | 1975-04-09 |
| FR2194193A5 (en, 2012) | 1974-02-22 |
| JPS4992098A (en, 2012) | 1974-09-03 |
| IE38310L (en) | 1974-01-31 |
| CA1013747A (fr) | 1977-07-12 |
| DK138454B (da) | 1978-09-11 |
| DK138454C (en, 2012) | 1979-02-19 |
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