GB845056A - Improvements in or relating to tropane derivatives - Google Patents
Improvements in or relating to tropane derivativesInfo
- Publication number
- GB845056A GB845056A GB20910/58A GB2091058A GB845056A GB 845056 A GB845056 A GB 845056A GB 20910/58 A GB20910/58 A GB 20910/58A GB 2091058 A GB2091058 A GB 2091058A GB 845056 A GB845056 A GB 845056A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrolysed
- oxidized
- derivatives
- acetyltropyl
- tropene
- 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
- 150000003813 tropane derivatives Chemical class 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 3
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 abstract 3
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 abstract 3
- XVCJZEFEPLMMNK-MYJAWHEDSA-N C(C)(=O)O[C@H]1C[C@H]2C=C[C@@H](C1)N2C Chemical compound C(C)(=O)O[C@H]1C[C@H]2C=C[C@@H](C1)N2C XVCJZEFEPLMMNK-MYJAWHEDSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 abstract 2
- GXSKBBRWKUAYEJ-JIGDXULJSA-N [C@H]12C[C@@H](C[C@H](C=C1)N2C)O Chemical class [C@H]12C[C@@H](C[C@H](C=C1)N2C)O GXSKBBRWKUAYEJ-JIGDXULJSA-N 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 229960002646 scopolamine Drugs 0.000 abstract 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 229940075930 picrate Drugs 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
Derivatives of 6:7b -epoxy-3a -hydroxytropane are prepared by the oxidation of the corresponding 6-tropen-3a -ol derivatives by means of 30-100% hydrogen peroxide together with one or more organic acids convertible to peracids. Preferred starting materials are 6-tropen-3a -ol esters and their quaternary ammonium salts. In examples: (1) 3a -acetoxy-6-tropene is oxidized with 90% H2O2 and formic acid to acetylscopine, characterized as its picrate: (2) 3a -acetoxy-6-tropene is hydrolysed with 2N HCl, the resulting tropenol hydrochloride is esterified with acetyltropyl chloride, and the ester is oxidized as in (1) to acetylscopolamine which is hydrolysed to scopolamine (or hyoscine if optically active acetyltropyl chloride is used); (3) tropenol hydrochloride is quaternized with n-butyl bromide and the product esterified, oxidized and hydrolysed as in (2) to yield finally(-)-scopolamine n-butobromide. Reference has been directed by the Comptroller to Specification 708,370.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU845056X | 1957-07-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB845056A true GB845056A (en) | 1960-08-17 |
Family
ID=10980597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20910/58A Expired GB845056A (en) | 1957-07-05 | 1958-06-30 | Improvements in or relating to tropane derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB845056A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE39820E1 (en) | 1989-09-16 | 2007-09-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
| US7879871B2 (en) | 2005-05-02 | 2011-02-01 | Boehringer Ingelheim International Gmbh | Crystalline forms of tiotropium bromide |
-
1958
- 1958-06-30 GB GB20910/58A patent/GB845056A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE39820E1 (en) | 1989-09-16 | 2007-09-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
| US7879871B2 (en) | 2005-05-02 | 2011-02-01 | Boehringer Ingelheim International Gmbh | Crystalline forms of tiotropium bromide |
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