GB1390304A - 1,2,3,4-tetrahydro-9h-pyrido-3,4b indole derivatives and their use as intermediates in the synthesis of eburnamonine - Google Patents
1,2,3,4-tetrahydro-9h-pyrido-3,4b indole derivatives and their use as intermediates in the synthesis of eburnamonineInfo
- Publication number
- GB1390304A GB1390304A GB3639273A GB3639273A GB1390304A GB 1390304 A GB1390304 A GB 1390304A GB 3639273 A GB3639273 A GB 3639273A GB 3639273 A GB3639273 A GB 3639273A GB 1390304 A GB1390304 A GB 1390304A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- pyrido
- tetrahydro
- july
- 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
- 150000002475 indoles Chemical class 0.000 title abstract 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
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 229950011119 eburnamonine Drugs 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
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 2
- -1 phosphorus compound Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 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 (OSRAM) | 1972-07-31 | 1972-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1390304A true GB1390304A (en) | 1975-04-09 |
Family
ID=9102588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3639273A Expired GB1390304A (en) | 1972-07-31 | 1973-07-31 | 1,2,3,4-tetrahydro-9h-pyrido-3,4b indole derivatives and their use as intermediates in the synthesis of eburnamonine |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3862160A (OSRAM) |
| JP (1) | JPS573676B2 (OSRAM) |
| BE (1) | BE802913A (OSRAM) |
| CA (1) | CA1013747A (OSRAM) |
| CH (1) | CH572926A5 (OSRAM) |
| DE (1) | DE2338838A1 (OSRAM) |
| DK (1) | DK138454B (OSRAM) |
| FR (1) | FR2194193A5 (OSRAM) |
| GB (1) | GB1390304A (OSRAM) |
| HU (1) | HU166483B (OSRAM) |
| IE (1) | IE38310B1 (OSRAM) |
| NL (1) | NL183824C (OSRAM) |
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 (OSRAM) * | 1986-02-18 | 1987-08-25 | ||
| JPH0323093U (OSRAM) * | 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 (OSRAM) | 1975-03-28 |
| NL183824C (nl) | 1989-02-01 |
| NL7310608A (OSRAM) | 1974-02-04 |
| US3862160A (en) | 1975-01-21 |
| JPS573676B2 (OSRAM) | 1982-01-22 |
| BE802913A (fr) | 1974-01-28 |
| DE2338838A1 (de) | 1974-02-14 |
| NL183824B (nl) | 1988-09-01 |
| CH572926A5 (OSRAM) | 1976-02-27 |
| FR2194193A5 (OSRAM) | 1974-02-22 |
| JPS4992098A (OSRAM) | 1974-09-03 |
| IE38310L (en) | 1974-01-31 |
| CA1013747A (fr) | 1977-07-12 |
| DK138454B (da) | 1978-09-11 |
| IE38310B1 (en) | 1978-02-15 |
| DK138454C (OSRAM) | 1979-02-19 |
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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 |