DE179212C - - Google Patents
Info
- Publication number
- DE179212C DE179212C DENDAT179212D DE179212DA DE179212C DE 179212 C DE179212 C DE 179212C DE NDAT179212 D DENDAT179212 D DE NDAT179212D DE 179212D A DE179212D A DE 179212DA DE 179212 C DE179212 C DE 179212C
- Authority
- DE
- Germany
- Prior art keywords
- berberine
- melting point
- ether
- water
- cyanide
- 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.)
- Active
Links
- -1 organometallic magnesium compounds Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000003836 berberines Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- YBHILYKTIRIUTE-UHFFFAOYSA-N berberine Chemical compound C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 YBHILYKTIRIUTE-UHFFFAOYSA-N 0.000 description 5
- 229940093265 berberine Drugs 0.000 description 5
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PAPMYQLKLNRZIR-UHFFFAOYSA-N Cotarnine Chemical compound C1CN(C)C(O)C2=C1C=C1OCOC1=C2OC PAPMYQLKLNRZIR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229940028332 halog Drugs 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
- VKJGBAJNNALVAV-UHFFFAOYSA-M Berberine chloride (TN) Chemical compound [Cl-].C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 VKJGBAJNNALVAV-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FZAGOOYMTPGPGF-UHFFFAOYSA-N Lambertine Chemical compound C1=C2C3=CC4=CC=C(OC)C(OC)=C4CN3CCC2=CC2=C1OCO2 FZAGOOYMTPGPGF-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE179212C true DE179212C (enrdf_load_stackoverflow) |
Family
ID=443548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT179212D Active DE179212C (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE179212C (enrdf_load_stackoverflow) |
-
0
- DE DENDAT179212D patent/DE179212C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1906527C3 (de) | Thioninderivate, Verfahren zu deren Herstellung und pharmazeutische Präparate, welche diese enthalten | |
| DE1795452A1 (de) | 2-Aryl-nitroimidazole und Verfahren zu deren Herstellung | |
| DE1294375B (de) | Verfahren zur Herstellung von antidepressiv wirksamen Aminopropyliden-9, 10-dihydroanthracenen | |
| DE179212C (enrdf_load_stackoverflow) | ||
| DE821976C (de) | Verfahren zur Herstellung neuer Monoazofarbstoffe der Pyrazolonreihe | |
| DE2123314A1 (de) | Neue Derivate von 6,6-Dimethyl-9alkyl-9-azabicyclo eckige Klammer auf 3.3.1 eckige Klammer zu nonan-301 und Verfahren zu deren Herstellung | |
| DE2166270C3 (de) | Nicotinoylaminoäthansulfonyl-2amino-thiazol | |
| DE539784C (de) | Verfahren zur Herstellung von Farbstoffen der Polymethinreihe | |
| DE976968C (de) | Verfahren zum Sensibilisieren fotografischer Halogensilber-Positiv- bzw. Kopieremulsionen | |
| DE964053C (de) | Verfahren zur Herstellung von eine primaere Aminogruppe enthaltenden monoquaternaeren Ammoniumverbindungen | |
| DE182217C (enrdf_load_stackoverflow) | ||
| DE514504C (de) | Verfahren zur Herstellung von Eisenkomplexsalzen | |
| DE270258C (enrdf_load_stackoverflow) | ||
| DE392067C (de) | Verfahren zur Darstellung von N-aralkylierten Imidazolylalkylaminen | |
| DE602089C (de) | Verfahren zur Darstellung neutraler wasserloeslicher Komplexsalze der Mercaptopyrimidine | |
| DE2029084C3 (de) | alpha-lsomeresdes Decansäureesters von 10- eckige Klammer auf 3-(4-Hydroxyäthyl-1 -piperazinyQ-propyliden eckige Klammer zu -2-trifhiormethylthioxanthen und dessen nicht-toxische Säureadditionssalze sowie Verfehlen zu seiner Herstellung | |
| DE454701C (de) | Verfahren zur Darstellung von in der 3, 4-Stellung symmetrisch disubstituierten Derivaten des Arsenostibiobenzols | |
| DE1768714C (de) | Verfahren zur Herstellung von Kobaltkomplexsalzen | |
| DE436780C (de) | Verfahren zur Darstellung von Wismutsalzen mercurierter, organischer, einen Saeurerest enthaltender Verbindungen | |
| DE68697C (de) | Verfahren zur Darstellung basischer Disulfidverbindungen (Thiurete) und von Salzen derselben aus Alkyldithiobiureten | |
| DE1902449A1 (de) | Verfahren zur Herstellung neuer Guanidin-Derivate | |
| DE30358C (de) | Verfahren zur Darstellung der Doppelverbindungen des Chlofjods mit den Basen der Chinolinreihe und zur Herstellung von Farbstoffen aus denselben | |
| DE1644636C (de) | Saure, diamino-substituierte vom Di arylamin abgeleitete Tnarylmethanfarb stoffe | |
| DE283305C (enrdf_load_stackoverflow) | ||
| DE139394C (enrdf_load_stackoverflow) |