GB1490659A - Quinuclidin-3-yl carbinols - Google Patents
Quinuclidin-3-yl carbinolsInfo
- Publication number
- GB1490659A GB1490659A GB587775A GB587775A GB1490659A GB 1490659 A GB1490659 A GB 1490659A GB 587775 A GB587775 A GB 587775A GB 587775 A GB587775 A GB 587775A GB 1490659 A GB1490659 A GB 1490659A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- quinuclidin
- carbinols
- formula
- image
- 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
- GUAWHSHTXVVCLZ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-ylmethanol Chemical class C1CC2C(CO)CN1CC2 GUAWHSHTXVVCLZ-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 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 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 230000003326 anti-histaminergic effect Effects 0.000 abstract 1
- 230000001705 anti-serotonergic effect Effects 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 239000003420 antiserotonin agent Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 230000007774 longterm Effects 0.000 abstract 1
- 150000002900 organolithium compounds Chemical class 0.000 abstract 1
- 150000002901 organomagnesium compounds Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 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)
- Medicines Containing Plant Substances (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
(Quinuclidin-3-yl)carbinols of the formula <IMAGE> where n = 0 or 1 and R and R' = optionally substituted phenyl, cyclohexyl or heteroaryl, R and R' being identical or not identical, are obtained in one or two steps from compounds of the formula <IMAGE> where R'' = -CN or -COO(lower alkyl) by reaction with organolithium or organomagnesium compounds. The compounds (1) have antihistamine, antiserotonin and antiallergic actions in combination with decreased toxicity. At the same time, they have a pronounced long-term action.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2002003A SU495310A1 (en) | 1974-03-05 | 1974-03-05 | Hinuclidyl-3-diaral (heteryl) carbinols exhibiting antihistamine, antiserotonin and antiallergic activity and a method for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1490659A true GB1490659A (en) | 1977-11-02 |
Family
ID=20577613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB587775A Expired GB1490659A (en) | 1974-03-05 | 1975-02-12 | Quinuclidin-3-yl carbinols |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH608015A5 (en) |
| DE (1) | DE2502916A1 (en) |
| FR (1) | FR2262985B1 (en) |
| GB (1) | GB1490659A (en) |
| SU (1) | SU495310A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006029549A1 (en) | 2004-09-15 | 2006-03-23 | Shuqiang Zhao | Quinuclidine compounds having quaternary ammonium group, it's preparation method and use as blocking agents of acetycholine |
| WO2013043961A1 (en) * | 2011-09-22 | 2013-03-28 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of choline kinase |
Families Citing this family (12)
| 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 (en) * | 1985-01-07 | 1988-10-31 | Sandoz Ag | CARBOCYCLIC AND HETEROCYCLIC CARBONYL METHYLENE AND METHYL PIPERIDINE AND PYRROLIDINE. |
| ES2061502T3 (en) * | 1986-06-27 | 1994-12-16 | Beecham Group Plc | NEW BRIDGED BICYCLE N-HETERO CYCLES. |
| 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 |
| SK282366B6 (en) * | 1994-08-24 | 2002-01-07 | Astra Aktiebolag | Spiro-azabicyclic compound, pharmaceutical preparation containing it, its preparation method, intermediates of this method and use in medicine |
| CA2493245A1 (en) * | 2002-08-14 | 2004-02-26 | Neurosearch A/S | Novel quinuclidine derivatives and their use |
-
1974
- 1974-03-05 SU SU2002003A patent/SU495310A1/en active
-
1975
- 1975-01-24 DE DE19752502916 patent/DE2502916A1/en 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/en not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006029549A1 (en) | 2004-09-15 | 2006-03-23 | Shuqiang Zhao | Quinuclidine compounds having quaternary ammonium group, it's preparation method and use as blocking agents of acetycholine |
| EP1790643A4 (en) * | 2004-09-15 | 2008-09-24 | Shuqiang Zhao | CHINUCLIDINE COMPOUNDS WITH QUATERNARM AMMONIUM GROUP, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS ACETYLCHOLINE BLOCKING AGENTS |
| WO2013043961A1 (en) * | 2011-09-22 | 2013-03-28 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of choline kinase |
| CN103814026A (en) * | 2011-09-22 | 2014-05-21 | 沃泰克斯药物股份有限公司 | Compounds useful as inhibitors of choline kinase |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2262985B1 (en) | 1978-12-01 |
| DE2502916A1 (en) | 1975-09-11 |
| DE2502916C2 (en) | 1988-03-17 |
| FR2262985A1 (en) | 1975-10-03 |
| SU495310A1 (en) | 1975-12-15 |
| CH608015A5 (en) | 1978-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |