SU495310A1 - Хинуклидил-3-диарал(гетерил) карбинолы, про вл ющие антигистаминную, антисеротониновую и антиаллергическую активность и способ их получени - Google Patents
Хинуклидил-3-диарал(гетерил) карбинолы, про вл ющие антигистаминную, антисеротониновую и антиаллергическую активность и способ их получениInfo
- Publication number
- SU495310A1 SU495310A1 SU2002003A SU2002003A SU495310A1 SU 495310 A1 SU495310 A1 SU 495310A1 SU 2002003 A SU2002003 A SU 2002003A SU 2002003 A SU2002003 A SU 2002003A SU 495310 A1 SU495310 A1 SU 495310A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hinuclidyl
- diaral
- antiserotonin
- heteryl
- carbinols
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 title 1
- 230000003266 anti-allergic effect Effects 0.000 title 1
- 230000003326 anti-histaminergic effect Effects 0.000 title 1
- 230000001705 anti-serotonergic effect Effects 0.000 title 1
- 239000000739 antihistaminic agent Substances 0.000 title 1
- 239000003420 antiserotonin agent Substances 0.000 title 1
- 230000001747 exhibiting effect Effects 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 229930013930 alkaloid Natural products 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241001233914 Chelidonium majus Species 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- INVGWHRKADIJHF-UHFFFAOYSA-N Sanguinarin Chemical compound C1=C2OCOC2=CC2=C3[N+](C)=CC4=C(OCO5)C5=CC=C4C3=CC=C21 INVGWHRKADIJHF-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229940068560 greater celandine Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- GHKISGDRQRSCII-ZOCIIQOWSA-N chelidonine Chemical group C1=C2[C@H]3N(C)CC4=C(OCO5)C5=CC=C4[C@H]3[C@@H](O)CC2=CC2=C1OCO2 GHKISGDRQRSCII-ZOCIIQOWSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- FCEXWTOTHXCQCQ-UHFFFAOYSA-N Ethoxydihydrosanguinarine Natural products C12=CC=C3OCOC3=C2C(OCC)N(C)C(C2=C3)=C1C=CC2=CC1=C3OCO1 FCEXWTOTHXCQCQ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 description 2
- 150000003836 berberines Chemical class 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229940084560 sanguinarine Drugs 0.000 description 2
- YZRQUTZNTDAYPJ-UHFFFAOYSA-N sanguinarine pseudobase Natural products C1=C2OCOC2=CC2=C3N(C)C(O)C4=C(OCO5)C5=CC=C4C3=CC=C21 YZRQUTZNTDAYPJ-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000011272 standard treatment Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- WEEFNMFMNMASJY-UHFFFAOYSA-M 1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium;chloride Chemical compound [Cl-].C1=C2OCOC2=CC2=CC=C3C4=CC=C(OC)C(OC)=C4C=[N+](C)C3=C21 WEEFNMFMNMASJY-UHFFFAOYSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- LLEJIEBFSOEYIV-UHFFFAOYSA-N Chelerythrine Natural products C1=C2OCOC2=CC2=CC=C3C4=CC=C(OC)C(OC)=C4C=[N+](C)C3=C21 LLEJIEBFSOEYIV-UHFFFAOYSA-N 0.000 description 1
- VINIVXVRXVXNTR-UHFFFAOYSA-N Chelidonin Natural products CN1Cc2c3OCOc3ccc2C4C(O)Cc5c6OCOc6ccc5C14 VINIVXVRXVXNTR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- RATMHCJTVBHJSU-UHFFFAOYSA-N Dihydrochelerythrine Natural products C1=C2OCOC2=CC2=C(N(C)C(O)C=3C4=CC=C(C=3OC)OC)C4=CC=C21 RATMHCJTVBHJSU-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000226172 Muracypraea mus Species 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 241000382509 Vania Species 0.000 description 1
- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 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 1
- 229940093265 berberine Drugs 0.000 description 1
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GHKISGDRQRSCII-UHFFFAOYSA-N chelidonine Natural products C1=C2C3N(C)CC4=C(OCO5)C5=CC=C4C3C(O)CC2=CC2=C1OCO2 GHKISGDRQRSCII-UHFFFAOYSA-N 0.000 description 1
- LVURMIFHBFKWNP-CIVDVNSDSA-N chelidonine hydrochloride Chemical compound [Cl-].C1=C2[C@@H]3[NH+](C)CC4=C(OCO5)C5=CC=C4[C@@H]3[C@H](O)CC2=CC2=C1OCO2 LVURMIFHBFKWNP-CIVDVNSDSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Plant Substances (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2002003A SU495310A1 (ru) | 1974-03-05 | 1974-03-05 | Хинуклидил-3-диарал(гетерил) карбинолы, про вл ющие антигистаминную, антисеротониновую и антиаллергическую активность и способ их получени |
| DE19752502916 DE2502916A1 (de) | 1974-03-05 | 1975-01-24 | (chinuklidyl-3)-diaryl(heteryl) karbinole, ihre salze und verfahren zu deren herstellung |
| GB587775A GB1490659A (en) | 1974-03-05 | 1975-02-12 | Quinuclidin-3-yl carbinols |
| FR7506586A FR2262985B1 (en:Method) | 1974-03-05 | 1975-03-03 | |
| CH277975A CH608015A5 (en) | 1974-03-05 | 1975-03-05 | Process for the preparation of (3-quinuclidyl)carbinols and their salts |
| US05/705,663 US4038402A (en) | 1974-03-05 | 1976-07-15 | Method of effecting antihistaminic, antiserotonin and antiallergic actions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2002003A SU495310A1 (ru) | 1974-03-05 | 1974-03-05 | Хинуклидил-3-диарал(гетерил) карбинолы, про вл ющие антигистаминную, антисеротониновую и антиаллергическую активность и способ их получени |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU495310A1 true SU495310A1 (ru) | 1975-12-15 |
Family
ID=20577613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2002003A SU495310A1 (ru) | 1974-03-05 | 1974-03-05 | Хинуклидил-3-диарал(гетерил) карбинолы, про вл ющие антигистаминную, антисеротониновую и антиаллергическую активность и способ их получени |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH608015A5 (en:Method) |
| DE (1) | DE2502916A1 (en:Method) |
| FR (1) | FR2262985B1 (en:Method) |
| GB (1) | GB1490659A (en:Method) |
| SU (1) | SU495310A1 (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2148058C1 (ru) * | 1994-08-24 | 2000-04-27 | Астра Актиеболаг | Спиро-азабициклические соединения, способы их получения и промежуточные продукты |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4125531A (en) * | 1977-04-18 | 1978-11-14 | G. D. Searle & Co. | 2-Substituted-1-azabicyclo[2.2.2]octanes |
| US4203989A (en) * | 1979-04-30 | 1980-05-20 | G. D. Searle & Co. | Anti-diarrheal diaryl-(1-azabicyclo(2.2.2)octan-2-yl)-alkanols and related compounds |
| CH667657A5 (de) * | 1985-01-07 | 1988-10-31 | Sandoz Ag | Carbocyclische und heterocyclische carbonylmethylen- und methylpiperidine und -pyrrolidine. |
| DE3789039T2 (de) * | 1986-06-27 | 1994-06-09 | Beecham Group Plc | Verbrückte bicyclische N-heterocyclische Verbindungen. |
| GB9122988D0 (en) * | 1991-10-30 | 1991-12-18 | Ici Plc | Heterocyclic compounds |
| EP0596058A1 (en) * | 1992-04-10 | 1994-05-11 | Zeneca Limited | Biphenylylquinuclidine derivatives as squalene synthase inhibitors |
| GB9211796D0 (en) * | 1992-06-04 | 1992-07-15 | Ici Plc | Heterocyclic derivatives |
| GB9216721D0 (en) * | 1992-08-06 | 1992-09-23 | Ici Plc | Therapeutic heterocyclic derivatives |
| GB9218334D0 (en) * | 1992-08-28 | 1992-10-14 | Ici Plc | Heterocyclic compounds |
| GB9226573D0 (en) * | 1992-12-21 | 1993-02-17 | Ici Plc | Heterocyclic compounds |
| BR0313153A (pt) * | 2002-08-14 | 2005-06-28 | Neurosearch As | Derivado de quinuclidina, composição farmacêutica, uso de um derivado de quinuclidina, e, método de tratamento, prevenção ou alìvio de uma doença ou um distúrbio ou uma condição de um corpo animal vivo |
| EP1790643B1 (en) * | 2004-09-15 | 2010-06-02 | Shuqiang Zhao | Quinuclidine compounds having quaternary ammonium group, it's preparation method and use as blocking agents of acetycholine |
| RU2014115952A (ru) * | 2011-09-22 | 2015-10-27 | Вертекс Фармасьютикалз Инкорпорейтед | Соединения, используемые в качестве ингибиторов холинкиназы |
-
1974
- 1974-03-05 SU SU2002003A patent/SU495310A1/ru active
-
1975
- 1975-01-24 DE DE19752502916 patent/DE2502916A1/de active Granted
- 1975-02-12 GB GB587775A patent/GB1490659A/en not_active Expired
- 1975-03-03 FR FR7506586A patent/FR2262985B1/fr not_active Expired
- 1975-03-05 CH CH277975A patent/CH608015A5/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2148058C1 (ru) * | 1994-08-24 | 2000-04-27 | Астра Актиеболаг | Спиро-азабициклические соединения, способы их получения и промежуточные продукты |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1490659A (en) | 1977-11-02 |
| DE2502916A1 (de) | 1975-09-11 |
| CH608015A5 (en) | 1978-12-15 |
| FR2262985A1 (en:Method) | 1975-10-03 |
| FR2262985B1 (en:Method) | 1978-12-01 |
| DE2502916C2 (en:Method) | 1988-03-17 |
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