ES327925A1 - A procedure for the production of hydrogenated derivatives of tebaina and oripavina. (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure for the production of hydrogenated derivatives of tebaina and oripavina. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES327925A1 ES327925A1 ES0327925A ES327925A ES327925A1 ES 327925 A1 ES327925 A1 ES 327925A1 ES 0327925 A ES0327925 A ES 0327925A ES 327925 A ES327925 A ES 327925A ES 327925 A1 ES327925 A1 ES 327925A1
- Authority
- ES
- Spain
- Prior art keywords
- group
- carbon atoms
- hydrogen atom
- formula
- compound
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/09—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
- C07D489/10—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14
- C07D489/12—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14 the bridge containing only two carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A process for the production of hydrogenated derivatives of thebaine and oripavine which are compounds of the formula: ** (See formula) ** where R represents a hydrogen atom, a methyl group, the group CnH2n + 1Co-, where n is an integer from 1 to 3 inclusive, benzoyl or nicotinyl; R1 represents a hydrogen atom, an alkyl, alkenyl or alkynyl group containing up to 8 carbon atoms, or an alicyclicly substituted methyl group in which the total number of carbon atoms is from 4 to 8; R 2 represents a hydrogen atom, an alkyl or alkenyl group containing up to 3 carbon atoms, an aryl group or a substituted aryl group; R3 represents a hydrogen atom, an alicyclic group containing from 4 to 8 carbon atoms, an alkyl, alkenyl or alkynyl group containing up to 8 carbon atoms, which may be substituted on carbon atoms numbers 1 to 4 (the carbon atoms # 1 are adjacent to the carbon atom bearing the alcoholic hydroxyl group) by an alicyclic, aryl, alkoxy, aryloxy or hetercyclic group containing oxygen provided that when R represents a hydrogen atom, R3 and R4 do not contain the -CH-aryl and -CH-C = C- systems attached directly to the carbon atom bearing the alcoholic hydroxyl group; whose process consists in hydrogenating, in the presence of a hydrogenation catalyst, (a) a compound of the formula: ** (See formula) ** where R1, R2 and R3 have the meaning given above, or (b) a compound of formula: ** (See formula) ** wherein R1 and R2 have the meaning given above, and reacting the hydrogenated product with an organometallic derivative, such as a Grignard reagent or an organolytic compound, in which the R3 group is attached to a metal atom, or (c) a compound of formula: ** (See formula) ** where ALK represents an alkyl radical, and reducing the hydrogenated product with lithium aluminum hydride to give a product in which R2 and R3 both represent a hydrogen atom and, at will, replace the radicals R and R1 with others of the same group , after stages (a), (b) or (c). (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25289/65A GB1136214A (en) | 1965-06-15 | 1965-06-15 | Thebaine and oripavine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES327925A1 true ES327925A1 (en) | 1967-04-01 |
Family
ID=10225305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0327925A Expired ES327925A1 (en) | 1965-06-15 | 1966-06-14 | A procedure for the production of hydrogenated derivatives of tebaina and oripavina. (Machine-translation by Google Translate, not legally binding) |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT272530B (en) |
| BE (1) | BE682551A (en) |
| BR (1) | BR6680359D0 (en) |
| CH (1) | CH558362A (en) |
| DE (1) | DE1620206A1 (en) |
| DK (1) | DK115926B (en) |
| ES (1) | ES327925A1 (en) |
| FI (1) | FI49724C (en) |
| FR (1) | FR6395M (en) |
| GB (1) | GB1136214A (en) |
| LU (1) | LU51306A1 (en) |
| NL (1) | NL6608255A (en) |
| NO (1) | NO119590B (en) |
| SE (1) | SE325276B (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2554816B1 (en) * | 1983-11-16 | 1986-09-26 | Sanofi Sa | NEW NORORIPAVIN DERIVATIVE HAVING BOTH AGONIST AND ANTAGONIST ACTIVITY OF MORPHINIC RECEPTORS |
| KR100204659B1 (en) * | 1996-05-28 | 1999-06-15 | 강재헌 | A novel analgesic compounds having buprenorphine structure |
| AUPQ968300A0 (en) | 2000-08-25 | 2000-09-21 | Glaxo Wellcome Australia Ltd | Chemical methods |
| GB2388369B (en) | 2002-05-10 | 2004-05-05 | Reckitt Benckiser Healthcare | Demethylation of thebaine derivative |
| GB0421687D0 (en) † | 2004-09-30 | 2004-11-03 | Johnson Matthey Plc | Preparation of opiate analgesics |
| CA2614223A1 (en) | 2005-02-24 | 2006-08-31 | Dr Pharma Nova, Llc | A registry method and control system for dea schedule ii-v medicines |
| DE102006054731B4 (en) | 2006-11-21 | 2013-02-28 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system for administration of the active ingredient buprenorphine and use thereof in pain therapy |
| EP2703404A1 (en) | 2008-07-30 | 2014-03-05 | Purdue Pharma L.P. | Buprenorphine analogs |
| WO2010039216A1 (en) * | 2008-09-30 | 2010-04-08 | Mallinckrodt Inc. | Processes for the alkylation of norbuprenorphine with reduced impurity formation |
| WO2010121369A1 (en) | 2009-04-24 | 2010-10-28 | Brock University | Processes for the preparation of morphinane and morphinone compounds |
| GB201111775D0 (en) | 2011-07-08 | 2011-08-24 | Univ Bath | Compounds and uses thereof |
| AR089201A1 (en) | 2011-12-12 | 2014-08-06 | Lohmann Therapie Syst Lts | TRANSDERMAL SUPPLY SYSTEM |
| RS61377B1 (en) | 2012-07-26 | 2021-02-26 | Camurus Ab | Opioid formulations |
| US9175000B2 (en) * | 2012-12-07 | 2015-11-03 | Purdue Pharma L.P. | Buprenorphine analogs |
| PT2810646T (en) | 2013-06-04 | 2016-10-05 | Lts Lohmann Therapie Systeme Ag | Transdermal delivery system |
| CA3238849A1 (en) | 2021-12-16 | 2023-06-22 | Arevipharma Gmbh | Method of making buprenorphine and precursor compounds thereof |
-
1965
- 1965-06-15 GB GB25289/65A patent/GB1136214A/en not_active Expired
-
1966
- 1966-06-10 NO NO163395A patent/NO119590B/no unknown
- 1966-06-13 LU LU51306A patent/LU51306A1/xx unknown
- 1966-06-13 FI FI661555A patent/FI49724C/en active
- 1966-06-14 BR BR180359/66A patent/BR6680359D0/en unknown
- 1966-06-14 NL NL6608255A patent/NL6608255A/xx unknown
- 1966-06-14 ES ES0327925A patent/ES327925A1/en not_active Expired
- 1966-06-14 SE SE08101/66A patent/SE325276B/xx unknown
- 1966-06-15 BE BE682551D patent/BE682551A/xx not_active IP Right Cessation
- 1966-06-15 DK DK307766AA patent/DK115926B/en unknown
- 1966-06-15 AT AT571566A patent/AT272530B/en active
- 1966-06-15 DE DE19661620206 patent/DE1620206A1/en active Pending
- 1966-06-15 CH CH861766A patent/CH558362A/en not_active IP Right Cessation
- 1966-06-15 FR FR65560A patent/FR6395M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK115926B (en) | 1969-11-24 |
| NO119590B (en) | 1970-06-08 |
| SE325276B (en) | 1970-06-29 |
| CH558362A (en) | 1975-01-31 |
| BE682551A (en) | 1966-11-14 |
| DE1620206A1 (en) | 1970-03-19 |
| NL6608255A (en) | 1966-12-16 |
| BR6680359D0 (en) | 1973-12-26 |
| GB1136214A (en) | 1968-12-11 |
| FI49724C (en) | 1975-09-10 |
| FR6395M (en) | 1968-10-21 |
| LU51306A1 (en) | 1966-08-16 |
| FI49724B (en) | 1975-06-02 |
| AT272530B (en) | 1969-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19870112 |