CA2487672A1 - Industrial process for preparing tropenol - Google Patents
Industrial process for preparing tropenol Download PDFInfo
- Publication number
- CA2487672A1 CA2487672A1 CA002487672A CA2487672A CA2487672A1 CA 2487672 A1 CA2487672 A1 CA 2487672A1 CA 002487672 A CA002487672 A CA 002487672A CA 2487672 A CA2487672 A CA 2487672A CA 2487672 A1 CA2487672 A1 CA 2487672A1
- Authority
- CA
- Canada
- Prior art keywords
- optionally
- formula
- buten
- acid addition
- denotes
- 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.)
- Granted
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to a novel, technically applicable production method f or preparing tropenol, optionally in the form of acid addition salts thereof.</ SDOAB>
Claims (5)
1) Process for preparing tropenol (I)
2) optionally in the form of the acid addition salts thereof, characterised in that a compound of formula (II) wherein R denotes a group selected from C1-C4-alkyl, C2-C6-alkenyl and C1-C4-alkylene-phenyl, each of which may be substituted by hydroxy or C1-C4-alkoxy, optionally in the form of the acid addition salts thereof as well as optionally in the form of the hydrates thereof, is reacted in a suitable solvent with a formamide-acetal of formula (III) wherein R' denotes C1-C4-alkyl and R" denotes a group selected from C1-C4-alkyl and C1-C4-alkylene-phenyl, to obtain a compound of formula IV
wherein the groups R, R' and R" may have the meanings given above, this is then converted by decarboxylation into an ester of formula (V) wherein R may have the meanings given above, and lastly this ester is saponified to obtain the compound of formula (I) which is optionally converted into an acid addition salt by reaction with a suitable acid.
2) Process according to claim 1, characterised in that a compound of formula (II) wherein R denotes C1-C4-alkyl or C2-C4-alkenyl, is used as starting material, optionally in the form of the acid addition salts thereof as well as optionally in the form of the hydrates thereof, and wherein in the formamide-acetal of formula (III) used the groups R' represent methyl or ethyl and the groups R" represent methyl, ethyl or propyl.
wherein the groups R, R' and R" may have the meanings given above, this is then converted by decarboxylation into an ester of formula (V) wherein R may have the meanings given above, and lastly this ester is saponified to obtain the compound of formula (I) which is optionally converted into an acid addition salt by reaction with a suitable acid.
2) Process according to claim 1, characterised in that a compound of formula (II) wherein R denotes C1-C4-alkyl or C2-C4-alkenyl, is used as starting material, optionally in the form of the acid addition salts thereof as well as optionally in the form of the hydrates thereof, and wherein in the formamide-acetal of formula (III) used the groups R' represent methyl or ethyl and the groups R" represent methyl, ethyl or propyl.
3) Process according to claim 1 or 2, characterised in that a compound of formula (II) wherein R denotes 1-propenyl, 2-propenyl, 1-buten-1-yl, 1-buten-2-yl, 1-buten-3-yl, 1-buten-4-yl, 2-buten-1-yl or 2-buten-2-yl, preferably 2-buten-2-yl, is used as starting material, optionally in the form of the acid addition salts thereof as well as optionally in the form of the hydrates thereof, and wherein in the formamide-acetal of formula (III) used the groups R' and R" represent methyl or ethyl, preferably methyl.
4) Use of compounds of formula (II) wherein R may have the meanings given in claims 1 to 3, optionally in the form of the acid addition salts thereof as well as optionally in the form of the hydrates thereof, as starting material for preparing therapeutically active compounds.
5) Use according to claim 4, characterised in that the therapeutically active compounds are tiotropium bromide, ipratropium bromide or BEA2108, preferably tiotropium bromide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2725704A CA2725704C (en) | 2002-05-31 | 2003-05-16 | Industrial process for preparing tropenol |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10224091A DE10224091A1 (en) | 2002-05-31 | 2002-05-31 | Technical process for the production of tropenol |
| DE10224091.4 | 2002-05-31 | ||
| PCT/EP2003/005158 WO2003101986A1 (en) | 2002-05-31 | 2003-05-16 | Technical method for producing tropenol |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2725704A Division CA2725704C (en) | 2002-05-31 | 2003-05-16 | Industrial process for preparing tropenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2487672A1 true CA2487672A1 (en) | 2003-12-11 |
| CA2487672C CA2487672C (en) | 2011-07-12 |
Family
ID=29432472
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2725704A Expired - Fee Related CA2725704C (en) | 2002-05-31 | 2003-05-16 | Industrial process for preparing tropenol |
| CA2487672A Expired - Fee Related CA2487672C (en) | 2002-05-31 | 2003-05-16 | Industrial process for preparing tropenol |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2725704A Expired - Fee Related CA2725704C (en) | 2002-05-31 | 2003-05-16 | Industrial process for preparing tropenol |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1513838B1 (en) |
| JP (1) | JP4610333B2 (en) |
| AT (1) | ATE334127T1 (en) |
| AU (1) | AU2003224159A1 (en) |
| CA (2) | CA2725704C (en) |
| DE (2) | DE10224091A1 (en) |
| DK (1) | DK1513838T3 (en) |
| ES (1) | ES2268351T3 (en) |
| WO (1) | WO2003101986A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2604742B1 (en) | 2011-12-13 | 2017-01-25 | Miele & Cie. KG | Operating element for a domestic appliance, operating unit for such a domestic appliance with such an operating element and domestic appliance with such an operating unit and such an operating element |
| CN111269226B (en) * | 2020-04-13 | 2021-09-21 | 石家庄四药有限公司 | Synthesis method of ipratropium bromide |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3931041C2 (en) * | 1989-09-16 | 2000-04-06 | Boehringer Ingelheim Kg | Esters of thienyl carboxylic acids with amino alcohols, their quaternization products, processes for their preparation and medicaments containing them |
| DE4108393A1 (en) * | 1991-03-15 | 1992-09-17 | Boehringer Ingelheim Kg | NEW ESTERS BI-AND TRICYCLIC AMINO ALCOHOLS, THEIR PREPARATION AND THEIR USE IN MEDICINAL PRODUCTS |
| DE10050994A1 (en) * | 2000-10-14 | 2002-04-18 | Boehringer Ingelheim Pharma | New diphenylalkanoic acid azabicyclooctane ester quaternary salts useful as anticholinergic agents, especially in treatment of asthma and chronic obstructive pulmonary disease |
-
2002
- 2002-05-31 DE DE10224091A patent/DE10224091A1/en not_active Withdrawn
-
2003
- 2003-05-16 EP EP03720568A patent/EP1513838B1/en not_active Expired - Lifetime
- 2003-05-16 AT AT03720568T patent/ATE334127T1/en active
- 2003-05-16 ES ES03720568T patent/ES2268351T3/en not_active Expired - Lifetime
- 2003-05-16 DE DE50304371T patent/DE50304371D1/en not_active Expired - Lifetime
- 2003-05-16 JP JP2004509677A patent/JP4610333B2/en not_active Expired - Lifetime
- 2003-05-16 CA CA2725704A patent/CA2725704C/en not_active Expired - Fee Related
- 2003-05-16 DK DK03720568T patent/DK1513838T3/en active
- 2003-05-16 CA CA2487672A patent/CA2487672C/en not_active Expired - Fee Related
- 2003-05-16 WO PCT/EP2003/005158 patent/WO2003101986A1/en active IP Right Grant
- 2003-05-16 AU AU2003224159A patent/AU2003224159A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE10224091A1 (en) | 2003-12-11 |
| CA2725704A1 (en) | 2003-12-11 |
| JP4610333B2 (en) | 2011-01-12 |
| DK1513838T3 (en) | 2006-11-13 |
| ATE334127T1 (en) | 2006-08-15 |
| EP1513838B1 (en) | 2006-07-26 |
| CA2487672C (en) | 2011-07-12 |
| WO2003101986A1 (en) | 2003-12-11 |
| JP2005531601A (en) | 2005-10-20 |
| AU2003224159A1 (en) | 2003-12-19 |
| ES2268351T3 (en) | 2007-03-16 |
| DE50304371D1 (en) | 2006-09-07 |
| CA2725704C (en) | 2013-06-11 |
| EP1513838A1 (en) | 2005-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160516 |