NO309266B1 - Fremgangsmåte for fremstilling av optisk anriket bupivacain - Google Patents

Fremgangsmåte for fremstilling av optisk anriket bupivacain Download PDF

Info

Publication number: NO309266B1
Authority: NO; Norway
Prior art keywords: solvent; bupivacaine; water; levobupivacaine; optically enriched
Prior art date: 1994-10-25

Application number

NO971903A

Other languages

English (en)

Norwegian (no)

Other versions

NO971903L (no

NO971903D0 (no

Inventor

Marianne Langston

Benjamin Mark Skead

Original Assignee

Darwin Discovery Ltd

Priority date (The priority date 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 date listed.)

1994-10-25

Filing date

1997-04-24

Publication date

2001-01-08

1994-10-25 Priority claimed from GB9421476A external-priority patent/GB9421476D0/en

1995-03-10 Priority claimed from GBGB9504926.8A external-priority patent/GB9504926D0/en

1997-04-24 Application filed by Darwin Discovery Ltd filed Critical Darwin Discovery Ltd

1997-04-24 Publication of NO971903L publication Critical patent/NO971903L/no

1997-04-24 Publication of NO971903D0 publication Critical patent/NO971903D0/no

2001-01-08 Publication of NO309266B1 publication Critical patent/NO309266B1/no

Links

238000000034 method Methods 0.000 title claims description 20
LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 title claims description 12
229960003150 bupivacaine Drugs 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title description 2
239000002904 solvent Substances 0.000 claims abstract description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract description 7
239000003795 chemical substances by application Substances 0.000 claims abstract description 6
239000011975 tartaric acid Substances 0.000 claims abstract description 6
235000002906 tartaric acid Nutrition 0.000 claims abstract description 5
238000006243 chemical reaction Methods 0.000 claims abstract description 4
229960004288 levobupivacaine Drugs 0.000 claims description 7
LEBVLXFERQHONN-INIZCTEOSA-N levobupivacaine Chemical compound CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-INIZCTEOSA-N 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 4
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical group OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
239000007787 solid Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229960001367 tartaric acid Drugs 0.000 description 5
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
239000012458 free base Substances 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000010410 layer Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
ZKMNUMMKYBVTFN-HNNXBMFYSA-N (S)-ropivacaine Chemical compound CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C ZKMNUMMKYBVTFN-HNNXBMFYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
229960001050 bupivacaine hydrochloride Drugs 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
NTBIYBAYFBNTCD-UHFFFAOYSA-N dibenzoyl 2,3-dihydroxybutanedioate Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229960001464 levobupivacaine hydrochloride Drugs 0.000 description 1
SIEYLFHKZGLBNX-NTISSMGPSA-N levobupivacaine hydrochloride (anhydrous) Chemical compound [Cl-].CCCC[NH+]1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C SIEYLFHKZGLBNX-NTISSMGPSA-N 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
229960001549 ropivacaine Drugs 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
JCQBWMAWTUBARI-UHFFFAOYSA-N tert-butyl 3-ethenylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(C=C)C1 JCQBWMAWTUBARI-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1

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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Hydrogenated Pyridines (AREA)
Peptides Or Proteins (AREA)
Investigating Or Analysing Biological Materials (AREA)
Saccharide Compounds (AREA)
Epoxy Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Compounds Of Unknown Constitution (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

NO971903A 1994-10-25 1997-04-24 Fremgangsmåte for fremstilling av optisk anriket bupivacain NO309266B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB9421476A GB9421476D0 (en)	1994-10-25	1994-10-25	Process and salt
GBGB9504926.8A GB9504926D0 (en)	1995-03-10	1995-03-10	Crystallisation
PCT/GB1995/002513 WO1996012699A1 (en)	1994-10-25	1995-10-23	Crystallisation of levobupivacaine and analogues thereof

Publications (3)

Publication Number	Publication Date
NO971903L NO971903L (no)	1997-04-24
NO971903D0 NO971903D0 (no)	1997-04-24
NO309266B1 true NO309266B1 (no)	2001-01-08

Family

ID=26305863

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO971903A NO309266B1 (no)	1994-10-25	1997-04-24	Fremgangsmåte for fremstilling av optisk anriket bupivacain

Country Status (16)

Country	Link
US (1)	US5994548A (es)
EP (1)	EP0788480B1 (es)
JP (1)	JP3911545B2 (es)
AT (1)	ATE245629T1 (es)
AU (1)	AU698637B2 (es)
CA (1)	CA2200355C (es)
DE (1)	DE69531356T2 (es)
DK (1)	DK0788480T3 (es)
ES (1)	ES2202375T3 (es)
FI (1)	FI117438B (es)
HU (1)	HU227420B1 (es)
MX (1)	MX9703024A (es)
NO (1)	NO309266B1 (es)
PL (1)	PL183210B1 (es)
PT (1)	PT788480E (es)
WO (1)	WO1996012699A1 (es)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR0002246A (pt)	2000-04-06	2003-04-15	Cristalia Prod Quimicos Farm	Processo de obtenção dos enantiÈmeros da bupivacaìna racêmica, processo de obtenção de composições farmacêuticas a base de levobupivacaìna: composições farmacêuticas a base de levobupivacaìna formuladas nas formas básicas ou sais farmaceuticamente aceitáveis e utilização das composições farmacêuticas a base de levobupivacaìna formuladas nas formas básicas ou sais farmaceuticamente aceitáveis
BRPI0104491B8 (pt) *	2001-10-10	2021-05-25	Cristalia Produtos Quim Farmaceuticos Ltda	n-(2,6-dimetilfenil)-1-propil-2-piperidinocarboxamida; processo de obtenção dos enantiômeros; mistura não racêmica dos anantiômeros e seu processo de obtenção e composição farmacêutica.
US20040001889A1 (en)	2002-06-25	2004-01-01	Guohua Chen	Short duration depot formulations
EP2959893A1 (en)	2002-12-13	2015-12-30	DURECT Corporation	Oral drug delivery system comprising high viscosity liquid carrier materials
US7094812B2 (en) *	2003-04-24	2006-08-22	Xerox Corporations	Colorant compositions
US6790267B1 (en) *	2003-04-24	2004-09-14	Xerox Corporation	Colorant compositions
PL1809329T3 (pl)	2004-09-17	2012-08-31	Durect Corp	Kompozycja znieczulająca zawierająca saib o przedłużonym uwalnianiu do stosowania miejscowego
US20070027105A1 (en)	2005-07-26	2007-02-01	Alza Corporation	Peroxide removal from drug delivery vehicle
JP2009535327A (ja) *	2006-04-25	2009-10-01	ディシュマン・ファーマシューティカルズ・アンド・ケミカルズ・リミテッド	ロピバカイン塩酸塩無水物およびその調製
US8337883B2 (en)	2006-11-03	2012-12-25	Durect Corporation	Transdermal delivery systems
WO2009088414A2 (en)	2007-12-06	2009-07-16	Durect Corporation	Oral pharmaceutical dosage forms
ES2383714T3 (es) *	2008-01-15	2012-06-25	Pharmathen S.A.	Proceso para preparar un compuesto (S)-1-alquil-2',6'-pipecoloxilidídico
US20100260844A1 (en)	2008-11-03	2010-10-14	Scicinski Jan J	Oral pharmaceutical dosage forms
CN103073484B (zh) *	2013-01-28	2014-10-22	山东诚创医药技术开发有限公司	一种甲哌卡因及其光学对映体的制备方法
CA2905131A1 (en)	2013-03-15	2014-09-18	Durect Corporation	Compositions with a rheological modifier to reduce dissolution variability
IL290150B2 (en) *	2016-12-26	2024-03-01	Cellix Bio Private Ltd	Compounds and methods for treating chronic pain
KR20220140711A (ko)	2020-01-13	2022-10-18	듀렉트 코퍼레이션	불순물이 감소된 지속 방출 약물 전달 시스템 및 관련 방법

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE341404B (es) *	1967-05-18	1971-12-27	Sterling Drug Inc
US4695576A (en) *	1984-07-09	1987-09-22	Astra Lake Medel Aktiebolag	L-N-n-propylpipecolic acid-2,6-xylidide

1995
- 1995-10-23 PT PT95934738T patent/PT788480E/pt unknown
- 1995-10-23 WO PCT/GB1995/002513 patent/WO1996012699A1/en active IP Right Grant
- 1995-10-23 CA CA002200355A patent/CA2200355C/en not_active Expired - Lifetime
- 1995-10-23 JP JP51373896A patent/JP3911545B2/ja not_active Expired - Lifetime
- 1995-10-23 HU HU9702372A patent/HU227420B1/hu unknown
- 1995-10-23 DK DK95934738T patent/DK0788480T3/da active
- 1995-10-23 AT AT95934738T patent/ATE245629T1/de active
- 1995-10-23 US US08/849,418 patent/US5994548A/en not_active Expired - Lifetime
- 1995-10-23 DE DE69531356T patent/DE69531356T2/de not_active Expired - Lifetime
- 1995-10-23 EP EP95934738A patent/EP0788480B1/en not_active Expired - Lifetime
- 1995-10-23 MX MX9703024A patent/MX9703024A/es unknown
- 1995-10-23 PL PL95319829A patent/PL183210B1/pl unknown
- 1995-10-23 AU AU37048/95A patent/AU698637B2/en not_active Expired
- 1995-10-23 ES ES95934738T patent/ES2202375T3/es not_active Expired - Lifetime
1997
- 1997-04-22 FI FI971711A patent/FI117438B/fi not_active IP Right Cessation
- 1997-04-24 NO NO971903A patent/NO309266B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE69531356D1 (de)	2003-08-28
NO971903L (no)	1997-04-24
FI971711A0 (fi)	1997-04-22
PL183210B1 (pl)	2002-06-28
DE69531356T2 (de)	2004-05-27
CA2200355A1 (en)	1996-05-02
DK0788480T3 (da)	2003-09-29
HU227420B1 (en)	2011-05-30
AU698637B2 (en)	1998-11-05
MX9703024A (es)	1997-10-31
FI971711A (fi)	1997-04-22
PL319829A1 (en)	1997-09-01
JP3911545B2 (ja)	2007-05-09
ATE245629T1 (de)	2003-08-15
NO971903D0 (no)	1997-04-24
HUT77631A (hu)	1998-06-29
FI117438B (fi)	2006-10-13
EP0788480B1 (en)	2003-07-23
JPH10507464A (ja)	1998-07-21
PT788480E (pt)	2003-12-31
US5994548A (en)	1999-11-30
WO1996012699A1 (en)	1996-05-02
CA2200355C (en)	2007-03-06
AU3704895A (en)	1996-05-15
EP0788480A1 (en)	1997-08-13
ES2202375T3 (es)	2004-04-01

Legal Events

Date	Code	Title	Description
2015-11-02	MK1K	Patent expired

Publication	Publication Date	Title
NO309266B1 (no)	2001-01-08	Fremgangsmåte for fremstilling av optisk anriket bupivacain
WO2007038277A2 (en)	2007-04-05	Resolution of alpha-(phenoxy) phenylacetic acid derivatives with naphthyl-alkylamines
AU696875B2 (en)	1998-09-17	New process for the preparation of ropivacaine hydrochloride monohydrate
AU2001278094B2 (en)	2006-01-12	Novel crystalline forms of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperindinyl]-1-hydroxybutyl]-alpha, alpha-dimethylbenzene acetic acid and its hydrochloride
JP2011012032A (ja)	2011-01-20	光学活性な３−アミノピペリジンの製造方法および製造の中間体
DK152752B (da)	1988-05-09	Fremgangsmaade til fremstilling af l-sulpirid
US7897777B2 (en)	2011-03-01	Process of enantiomeric resolution of D,L-(±)-threo-methylphenidate
KR100472609B1 (ko)	2005-07-07	레보부피바카인과그의유사체의결정화벙법
CN111302996A (zh)	2020-06-19	一种高手性纯度的富马酸氯马斯汀的制备方法
US20200131126A1 (en)	2020-04-30	Process for the Separation of Optical Isomers of Racemic 3-Alkylpiperidine-Carboxylic Acid Ethyl Esters
JP4000113B2 (ja)	2007-10-31	（３ｓ）−３−メトキシカルボニル−４−フェニル酪酸金属塩およびその使用方法
WO2002068391A1 (en)	2002-09-06	Process for resolving racemic mixtures of piperidine derivatives
WO2021166934A1 (ja)	2021-08-26	ピロリジン化合物の製造方法
US20040039206A1 (en)	2004-02-26	Process for resolving racemic mixtures of piperidine derivatives
CN117510398A (zh)	2024-02-06	一种高光学纯度(3r,4r)/(3s,4s)-n-boc-4-氨基-3-羟基哌啶的制备方法
WO2010079605A1 (ja)	2010-07-15	高純度１－ベンジル－３－アミノピロリジンの製造方法
EP1178962A1 (en)	2002-02-13	Process for the preparation of paroxetine acetate and analogues thereof
JPH0940621A (ja)	1997-02-10	光学活性インダニルメチルアミン誘導体及びその製造法
WO2000039121A1 (en)	2000-07-06	Process for the preparation of an acetate salt of paroxetine or paroxetine analogues
JPH0687828A (ja)	1994-03-29	環化反応を用いるジフルオロメチル化合物の合成
EP1140912A1 (en)	2001-10-10	Process for the preparation of an acetate salt of paroxetine or paroxetine analogues