US3847924A - Certain scopolammonium compounds - Google Patents
Certain scopolammonium compounds Download PDFInfo
- Publication number
- US3847924A US3847924A US00365728A US36572873A US3847924A US 3847924 A US3847924 A US 3847924A US 00365728 A US00365728 A US 00365728A US 36572873 A US36572873 A US 36572873A US 3847924 A US3847924 A US 3847924A
- Authority
- US
- United States
- Prior art keywords
- scopolammonium
- compound
- compounds
- observed
- certain
- 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 - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
Definitions
- scopolamine, atropine and hyoscyamine base are the essential components of the alkaloids contained in belladonna and scopolia. These compounds exhibit a strong parasympathetic blocking activity and they therefore are utilized for the purpose of therapeutical treatment of diseases such as gastric cramp, gastric ulcer, duodenal ulcer and the like. Unfortunately it was found that they show undesirable side effects such as thirst, dysuria, and palpitation and the injurious effects on central nervous system, such as illusion, hemicrania, nausea and the like.
- Compound A N-(p-butoxybenzyl)scopolammonium bromide
- Compound B the hitherto known butyl scopolammonium bromide
- R and X have the same meanings as previously defined with respect to the formula given to the opening paragraph.
- Typical solvents which have been found preferable to carry out the above reaction include lower alcohol, acetone, ether, chloroform and the like.
- the reaction takes place readily at room temperature. In order to avoid the racemisation of the scopolamine compounds, it is advisable to carry out the reaction at a low temperature.
- the resulting N-(p-loweralkoxybenzyl)scopolammonium bromides are easily soluble in Water.
- the aqueous solutions thus obtained are stable to heat with no tendency of causing racemisation. The fact olfers one of the serious advantages in the production of pharmaceutical preparations.
- R is a lower alkyl group and X is a halogen atom.
- a compound according to claim 1 which is pmethoxybenzyl scopolarnmonium bromide.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47057633A JPS4919012A (US07935154-20110503-C00018.png) | 1972-06-12 | 1972-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3847924A true US3847924A (en) | 1974-11-12 |
Family
ID=13061285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00365728A Expired - Lifetime US3847924A (en) | 1972-06-12 | 1973-05-31 | Certain scopolammonium compounds |
Country Status (11)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3952108A (en) * | 1972-04-18 | 1976-04-20 | Istituto De Angeli S.P.A. | Scopolamine derivatives for treating ulcers and spasms |
| AU760009B2 (en) * | 1997-10-24 | 2003-05-08 | Newlaxant Llc | Bis-quaternary ammonium derivatives as neuromuscular relaxants |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0622991Y2 (ja) * | 1990-02-28 | 1994-06-15 | 沖電気工業株式会社 | 化合物半導体ウエハ |
| RU2450143C1 (ru) * | 2011-03-16 | 2012-05-10 | Открытое акционерное общество "Научно-производственное объединение "Сатурн" (ОАО "НПО "Сатурн") | Газотурбинный двигатель |
| RU2450142C1 (ru) * | 2011-03-16 | 2012-05-10 | Открытое акционерное общество "Научно-производственное объединение "Сатурн" (ОАО "НПО "Сатурн") | Газотурбинный двигатель |
| RU2450141C1 (ru) * | 2011-03-16 | 2012-05-10 | Открытое акционерное общество "Научно-производственное объединение "Сатурн" (ОАО "НПО "Сатурн") | Газотурбинный двигатель |
| RU2450144C1 (ru) * | 2011-03-16 | 2012-05-10 | Открытое акционерное общество "Научно-производственное объединение "Сатурн" (ОАО "НПО "Сатурн") | Газотурбинный двигатель |
| RU2459967C1 (ru) * | 2011-04-05 | 2012-08-27 | Открытое акционерное общество "Научно-производственное объединение "Сатурн" (ОАО "НПО "Сатурн") | Двухконтурный газотурбинный двигатель |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH77A (de) * | 1889-01-09 | Christian Herren | Wurzelschneidmaschine |
-
1972
- 1972-06-12 JP JP47057633A patent/JPS4919012A/ja active Pending
-
1973
- 1973-05-31 US US00365728A patent/US3847924A/en not_active Expired - Lifetime
- 1973-06-06 NL NL7307903A patent/NL7307903A/xx not_active Application Discontinuation
- 1973-06-07 CH CH827873A patent/CH572933A5/xx not_active IP Right Cessation
- 1973-06-07 SE SE7308071A patent/SE403113B/xx unknown
- 1973-06-08 PH PH14709A patent/PH10925A/en unknown
- 1973-06-12 DE DE2329893A patent/DE2329893A1/de active Pending
- 1973-06-12 AU AU56805/73A patent/AU468339B2/en not_active Expired
- 1973-06-12 CA CA173,797A patent/CA1006519A/en not_active Expired
- 1973-06-12 GB GB2789573A patent/GB1378127A/en not_active Expired
- 1973-06-12 FR FR7321306A patent/FR2187354B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3952108A (en) * | 1972-04-18 | 1976-04-20 | Istituto De Angeli S.P.A. | Scopolamine derivatives for treating ulcers and spasms |
| AU760009B2 (en) * | 1997-10-24 | 2003-05-08 | Newlaxant Llc | Bis-quaternary ammonium derivatives as neuromuscular relaxants |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7307903A (US07935154-20110503-C00018.png) | 1973-12-14 |
| AU5680573A (en) | 1974-12-12 |
| FR2187354B1 (US07935154-20110503-C00018.png) | 1977-09-09 |
| DE2329893A1 (de) | 1974-01-03 |
| CA1006519A (en) | 1977-03-08 |
| JPS4919012A (US07935154-20110503-C00018.png) | 1974-02-20 |
| FR2187354A1 (US07935154-20110503-C00018.png) | 1974-01-18 |
| AU468339B2 (en) | 1976-01-08 |
| GB1378127A (en) | 1974-12-18 |
| CH572933A5 (US07935154-20110503-C00018.png) | 1976-02-27 |
| PH10925A (en) | 1977-10-05 |
| SE403113B (sv) | 1978-07-31 |
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