GB1199338A - Berbine Derivatives - Google Patents
Berbine DerivativesInfo
- Publication number
- GB1199338A GB1199338A GB310268A GB310268A GB1199338A GB 1199338 A GB1199338 A GB 1199338A GB 310268 A GB310268 A GB 310268A GB 310268 A GB310268 A GB 310268A GB 1199338 A GB1199338 A GB 1199338A
- Authority
- GB
- United Kingdom
- Prior art keywords
- berbine
- dehydroberbine
- alkoxyphenyl
- acid addition
- acid
- 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
- BRLDZKPJJNASGG-KRWDZBQOSA-N alpha-berbine Chemical class C1=CC=C2CN3CCC4=CC=CC=C4[C@@H]3CC2=C1 BRLDZKPJJNASGG-KRWDZBQOSA-N 0.000 title abstract 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- BRLDZKPJJNASGG-UHFFFAOYSA-N berbine Chemical compound C1=CC=C2CN3CCC4=CC=CC=C4C3CC2=C1 BRLDZKPJJNASGG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000003947 ethylamines Chemical class 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229940015043 glyoxal Drugs 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,199,338. Berbine derivatives. ROUSSEL UCLAF. 19 Jan., 1968 [20 Jan., 1967], No. 3102/68. Heading C2C. The invention comprises novel N-(3-alkoxybenzylidene) (or 3-alkoxybenzyl) #-(3-alkoxyphenyl) ethylamines and acid addition salts thereof, which compounds are prepared by reaction of a #-(3-alkoxyphenyl) ethylamine with a 3-alkoxybenzaldehyde with subsequent reduction of the imine to give the amine with an alkali metal borohydride and a process for the production of compounds possessing a berbine ring system substituted by alkoxy groups in the 3- and 10-positions which comprises reacting an N-(3- alkoxy-benzyl) #-(3-alkoxyphenyl) ethylamine in the form of an acid addition salt thereof with glyoxal, which reaction is advantageously effected in the presence of a polar solvent, e.g. water or dioxan, and in the presence of a strong organic acid. Formic acid in the presence of water is particularly preferred. A mixture of 13-dehydroberbine and an acid addition salt of a 7,13-bis-dehydroberbine is obtained and at least one of said dehydroberbine derivatives is reduced, preferably by using an alkali metal borohydride, e.g. NaBH 4 , KBH 4 , hydrogen in the presence of a palladium catalyst, or zinc in the presence of acetic acid, to obtain the desired berbine derivative having alkoxy groups in the 3- and 10-positions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR91949 | 1967-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1199338A true GB1199338A (en) | 1970-07-22 |
Family
ID=8624171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB310268A Expired GB1199338A (en) | 1967-01-20 | 1968-01-19 | Berbine Derivatives |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH485726A (en) |
| DE (1) | DE1668644A1 (en) |
| FR (1) | FR1568738A (en) |
| GB (1) | GB1199338A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4645772A (en) * | 1982-12-14 | 1987-02-24 | Urpha | Levorotatory enantiomers of derivatives of 5,6,13,13a-tetrahydro-8H-dibenzo [A,G]quinolizine, preparative process, pharmaceutical compositions containing them and application |
| CN111100122A (en) * | 2018-10-26 | 2020-05-05 | 刘力 | Novel levo-tetrahydropalmatine compound |
| CN118126034A (en) * | 2024-05-06 | 2024-06-04 | 云南省药物研究所 | Comprehensive utilization method of rotundine splitting mother liquor |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW460464B (en) * | 1996-11-25 | 2001-10-21 | Nippon Kayaku Kk | Novel phenanthridinium derivative having an anti-tumor activity and pharmaceutical composition containing the same |
| CN109843455A (en) | 2016-10-06 | 2019-06-04 | S·维德哈姆 | Apparatus and method for binding dust |
-
1967
- 1967-01-20 FR FR1568738D patent/FR1568738A/fr not_active Expired
-
1968
- 1968-01-15 CH CH55068A patent/CH485726A/en not_active IP Right Cessation
- 1968-01-17 DE DE19681668644 patent/DE1668644A1/en active Pending
- 1968-01-19 GB GB310268A patent/GB1199338A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4645772A (en) * | 1982-12-14 | 1987-02-24 | Urpha | Levorotatory enantiomers of derivatives of 5,6,13,13a-tetrahydro-8H-dibenzo [A,G]quinolizine, preparative process, pharmaceutical compositions containing them and application |
| CN111100122A (en) * | 2018-10-26 | 2020-05-05 | 刘力 | Novel levo-tetrahydropalmatine compound |
| CN118126034A (en) * | 2024-05-06 | 2024-06-04 | 云南省药物研究所 | Comprehensive utilization method of rotundine splitting mother liquor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1668644A1 (en) | 1972-02-24 |
| CH485726A (en) | 1970-02-15 |
| FR1568738A (en) | 1969-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |