GB1180712A - Novel levo-1-n-butyl-2',6'-pipecoloxylidide and the Preparation Thereof - Google Patents
Novel levo-1-n-butyl-2',6'-pipecoloxylidide and the Preparation ThereofInfo
- Publication number
- GB1180712A GB1180712A GB22420/68A GB2242068A GB1180712A GB 1180712 A GB1180712 A GB 1180712A GB 22420/68 A GB22420/68 A GB 22420/68A GB 2242068 A GB2242068 A GB 2242068A GB 1180712 A GB1180712 A GB 1180712A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pipecoloxylidide
- butyl
- levo
- tartrate
- dextro
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,180,712. Levo - -1 - n - Butyl - 2<SP>1</SP>,6<SP>1</SP> - pipecoloxylidide. STERLING DRUG Inc. 10 May, 1968 [18 May, 1967], No. 22420/68. Heading C2C. Novel levo - 1 - n - butyl - 2<SP>1</SP>,6<SP>1</SP>- pipecoloxylidide, free or substantially free from its optical antipode, and acid addition salts thereof are prepared (a) by reacting dl-2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide with O,O-dibenzoyl-d-tartaric acid to form a mixture of the diastereoisomeric O,O-dibenzoyl-d-tartrates, treating said mixture with boiling acetone, separating the acetone-insoluble dextro - 21,61 - pipecoloxylidide O,O - dibenzoyl - d-tartrate, isolating the levo-2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide O,O-dibenzoyl-d-tartrate from the acetone solution thereof, generating the levo-2<SP>1</SP>,6<SP>1</SP>- pipecoloxylidide base, e.g. with an inorganic base, from its O,O-dibenzoyl-d-tartrate and N- butylating said base, e.g. with n-butyraldehyde under catalytically hydrogenating conditions or with an n-butyl halide in the presence of an acid binding agent; or (b) by seeding an acetone or isopropanol solution of dl-1-n-butyl-2<SP>1</SP>,6<SP>1</SP>- pipecoloxylidide d-tartrate with dextro-1-n-butyl- 2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide d-tartrate, separating the resulting crystalline dextro-1-n-butyl-2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide d-tartrate, which may be hydrolysed to dextro-1-n-butyl-2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide, e.g. with aqueous ammonia, and either evaporating the acetone solution to yield levo-1-nbutyl - 2<SP>1</SP>,6<SP>1</SP> - pipecoloxylidide d - tartrate or treating the isopropanol filtrate with d-tartaric acid, seeding with levo-1-n-butyl-2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide d-bitartrate and separating the resulting crystalline levo-1-n-butyl-2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide d-bitartrate, with the further step of generating the levo-1-n-butyl-2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide base from its d-tartrate or d-bitartrate, e.g. with an inorganic base; followed optionally by converting the product to an acid addition salt thereof. Dextro-2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide is prepared by generating the free base from the O,O-dibenzoyld-tartrate prepared in (a) above, e.g. with an inorganic base, and may be N-butylated to give dextro-1-n-butyl-2<SP>1</SP>,6<SP>1</SP>-pipecoloxylidide. Levo - 1 - n - butyl - 2<SP>1</SP>,6<SP>1</SP> - pipecoloxylidide has longer acting local anaesthetic activity and is less toxic than its dextro-isomer and the dlform.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63927767A | 1967-05-18 | 1967-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1180712A true GB1180712A (en) | 1970-02-11 |
Family
ID=24563449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22420/68A Expired GB1180712A (en) | 1967-05-18 | 1968-05-10 | Novel levo-1-n-butyl-2',6'-pipecoloxylidide and the Preparation Thereof |
Country Status (13)
| Country | Link |
|---|---|
| AT (2) | AT286298B (en) |
| BE (1) | BE715188A (en) |
| CH (1) | CH498834A (en) |
| DE (1) | DE1770408C3 (en) |
| DK (1) | DK129234B (en) |
| ES (1) | ES354352A1 (en) |
| FI (1) | FI50333C (en) |
| FR (2) | FR1583872A (en) |
| GB (1) | GB1180712A (en) |
| IL (1) | IL29958A (en) |
| NL (1) | NL6806995A (en) |
| NO (1) | NO124540B (en) |
| SE (1) | SE341404B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996036606A1 (en) * | 1995-05-16 | 1996-11-21 | Astra Aktiebolag (Publ) | New process for the preparation of ropivacaine hydrochloride monohydrate |
| US5994548A (en) * | 1994-10-25 | 1999-11-30 | Darwin Discovery Ltd. | Crystallisation of levibupivacaine and analogues thereof |
| KR100844336B1 (en) * | 2007-01-16 | 2008-07-07 | 하나제약 주식회사 | New synthetic method of levobupivacaine and its hydrochloride |
| WO2014009964A1 (en) * | 2012-07-11 | 2014-01-16 | Neon Laboratories Limited | Process for enantiomeric enrichment of 2 ', 6 ' - pipecoloxylidide |
| CN105315196A (en) * | 2015-11-28 | 2016-02-10 | 山东齐都药业有限公司 | High-purity levobupivacaine hydrochloride refining method |
| CN109896992A (en) * | 2017-12-08 | 2019-06-18 | 武汉软件工程职业学院 | Prepare the method and its application of ionic liquid |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0151110B1 (en) * | 1983-08-01 | 1989-03-01 | Astra Läkemedel Aktiebolag | L-n-n-propylpipecolic acid-2,6-xylidide and method for preparing the same |
| SE451840B (en) * | 1986-01-03 | 1987-11-02 | Astra Laekemedel Ab | OPTICALLY PURE MONOHYDRATED OF S - (-) - 1-PROPYL-2 ', 6'-PIPECOLOXYLIDE HYDROCHLORIDE, SET TO PREPARE THIS AND PHARMACEUTICAL PREPARATIONS FOR LOCAL ANCHORING |
-
1968
- 1968-05-02 SE SE05905/68A patent/SE341404B/xx unknown
- 1968-05-07 IL IL29958A patent/IL29958A/en unknown
- 1968-05-10 NO NO1819/68A patent/NO124540B/no unknown
- 1968-05-10 GB GB22420/68A patent/GB1180712A/en not_active Expired
- 1968-05-14 DE DE1770408A patent/DE1770408C3/en not_active Expired
- 1968-05-15 BE BE715188D patent/BE715188A/xx unknown
- 1968-05-16 ES ES354352A patent/ES354352A1/en not_active Expired
- 1968-05-16 DK DK226968AA patent/DK129234B/en unknown
- 1968-05-17 CH CH733568A patent/CH498834A/en not_active IP Right Cessation
- 1968-05-17 FR FR1583872D patent/FR1583872A/fr not_active Expired
- 1968-05-17 AT AT1097469A patent/AT286298B/en not_active IP Right Cessation
- 1968-05-17 AT AT475368A patent/AT284843B/en not_active IP Right Cessation
- 1968-05-17 FI FI681394A patent/FI50333C/en active
- 1968-05-17 NL NL6806995A patent/NL6806995A/xx unknown
- 1968-08-16 FR FR163282A patent/FR8160M/fr not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5994548A (en) * | 1994-10-25 | 1999-11-30 | Darwin Discovery Ltd. | Crystallisation of levibupivacaine and analogues thereof |
| WO1996036606A1 (en) * | 1995-05-16 | 1996-11-21 | Astra Aktiebolag (Publ) | New process for the preparation of ropivacaine hydrochloride monohydrate |
| US5959112A (en) * | 1995-05-16 | 1999-09-28 | Astra Aktiebolag | Process for the preparation of ropivacaine hydrochloride monohydrate |
| CN1121388C (en) * | 1995-05-16 | 2003-09-17 | 阿斯特拉公司 | Process for the prepn. of ropivacaine hydrochloride monohydrate |
| KR100844336B1 (en) * | 2007-01-16 | 2008-07-07 | 하나제약 주식회사 | New synthetic method of levobupivacaine and its hydrochloride |
| WO2014009964A1 (en) * | 2012-07-11 | 2014-01-16 | Neon Laboratories Limited | Process for enantiomeric enrichment of 2 ', 6 ' - pipecoloxylidide |
| CN105315196A (en) * | 2015-11-28 | 2016-02-10 | 山东齐都药业有限公司 | High-purity levobupivacaine hydrochloride refining method |
| CN109896992A (en) * | 2017-12-08 | 2019-06-18 | 武汉软件工程职业学院 | Prepare the method and its application of ionic liquid |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1770408B2 (en) | 1974-04-11 |
| IL29958A (en) | 1971-04-28 |
| AT284843B (en) | 1970-09-25 |
| IL29958A0 (en) | 1968-07-25 |
| FR1583872A (en) | 1969-12-05 |
| NL6806995A (en) | 1968-11-19 |
| FI50333C (en) | 1976-02-10 |
| FR8160M (en) | 1970-08-24 |
| CH498834A (en) | 1970-11-15 |
| SE341404B (en) | 1971-12-27 |
| DE1770408A1 (en) | 1971-10-21 |
| FI50333B (en) | 1975-10-31 |
| NO124540B (en) | 1972-05-02 |
| DK129234B (en) | 1974-09-16 |
| DK129234C (en) | 1975-02-03 |
| DE1770408C3 (en) | 1974-11-07 |
| ES354352A1 (en) | 1969-11-01 |
| BE715188A (en) | 1968-09-30 |
| AT286298B (en) | 1970-12-10 |
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