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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Plant Substances (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 (enrdf_load_stackoverflow) | 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 (enrdf_load_stackoverflow) |
| DE (1) | DE2502916A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2262985B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1490659A (enrdf_load_stackoverflow) |
| SU (1) | SU495310A1 (enrdf_load_stackoverflow) |
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. |
| ES2061502T3 (es) * | 1986-06-27 | 1994-12-16 | Beecham Group Plc | Nuevos n-heterociclos biciclicos puenteados. |
| GB9122988D0 (en) * | 1991-10-30 | 1991-12-18 | Ici Plc | Heterocyclic compounds |
| US5612352A (en) * | 1992-04-10 | 1997-03-18 | Zeneca Limited | Heterocyclic compounds |
| 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 |
| US20050245567A1 (en) * | 2002-08-14 | 2005-11-03 | Dan Peters | Novel quinuclidine derivatives and their use |
| ES2344842T3 (es) * | 2004-09-15 | 2010-09-08 | Shuqiang Zhao | Compuestos de quinuclidina que tienen un grupo amonio cuaternario, su metodo de preparacion y uso como agentes bloqueantes de la acetilcolina. |
| 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 |
|---|---|
| FR2262985B1 (enrdf_load_stackoverflow) | 1978-12-01 |
| FR2262985A1 (enrdf_load_stackoverflow) | 1975-10-03 |
| GB1490659A (en) | 1977-11-02 |
| DE2502916C2 (enrdf_load_stackoverflow) | 1988-03-17 |
| CH608015A5 (en) | 1978-12-15 |
| DE2502916A1 (de) | 1975-09-11 |
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