IT1319195B1 - Processo per la produzione dell'acido r(+)alfa-lipoico. - Google Patents

Processo per la produzione dell'acido r(+)alfa-lipoico.

Info

Publication number: IT1319195B1
Authority: IT; Italy
Prior art keywords: alpha; lipoic acid; methylbenzylamine; acid; salt
Prior art date: 2000-10-10

Application number

IT2000MI002187A

Other languages

English (en)

Inventor

Flavio Villani

Antonio Nardi

Annibale Salvi

Giovanna Falabella

Original Assignee

Laboratorio Chimico Int Spa

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.)

2000-10-10

Filing date

2000-10-10

Publication date

2003-09-26

2000-10-10 Application filed by Laboratorio Chimico Int Spa filed Critical Laboratorio Chimico Int Spa

2000-10-10 Publication of ITMI20002187A0 publication Critical patent/ITMI20002187A0/it

2000-10-10 Priority to IT2000MI002187A priority Critical patent/IT1319195B1/it

2001-10-08 Priority to AU2002223603A priority patent/AU2002223603A1/en

2001-10-08 Priority to KR1020037004733A priority patent/KR100838922B1/ko

2001-10-08 Priority to ES01986685T priority patent/ES2254522T3/es

2001-10-08 Priority to CZ20031006A priority patent/CZ302932B6/cs

2001-10-08 Priority to EP01986685A priority patent/EP1330450B1/en

2001-10-08 Priority to DE60116796T priority patent/DE60116796T2/de

2001-10-08 Priority to JP2002534304A priority patent/JP4257573B2/ja

2001-10-08 Priority to PCT/EP2001/011575 priority patent/WO2002030918A2/en

2001-10-08 Priority to AT01986685T priority patent/ATE316082T1/de

2001-10-08 Priority to US10/398,892 priority patent/US6670484B2/en

2002-04-10 Publication of ITMI20002187A1 publication Critical patent/ITMI20002187A1/it

2003-09-26 Application granted granted Critical

2003-09-26 Publication of IT1319195B1 publication Critical patent/IT1319195B1/it

Links

AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 title abstract 6
AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 title abstract 4
238000000034 method Methods 0.000 title abstract 2
150000003839 salts Chemical class 0.000 abstract 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
238000001953 recrystallisation Methods 0.000 abstract 2
238000000926 separation method Methods 0.000 abstract 2
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 abstract 1
239000002253 acid Substances 0.000 abstract 1
150000007513 acids Chemical class 0.000 abstract 1
-1 aliphatic hydroxy-carboxylic acids Chemical class 0.000 abstract 1
229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
230000015572 biosynthetic process Effects 0.000 abstract 1
125000004432 carbon atom Chemical group C* 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 abstract 1
238000001914 filtration Methods 0.000 abstract 1
235000019136 lipoic acid Nutrition 0.000 abstract 1
239000000203 mixture Substances 0.000 abstract 1
239000012454 non-polar solvent Substances 0.000 abstract 1
239000002798 polar solvent Substances 0.000 abstract 1
238000000746 purification Methods 0.000 abstract 1
239000002904 solvent Substances 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
229960002663 thioctic acid Drugs 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/06—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols from sulfides, hydropolysulfides or polysulfides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IT2000MI002187A 2000-10-10 2000-10-10 Processo per la produzione dell'acido r(+)alfa-lipoico. IT1319195B1 (it)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
IT2000MI002187A IT1319195B1 (it)	2000-10-10	2000-10-10	Processo per la produzione dell'acido r(+)alfa-lipoico.
DE60116796T DE60116796T2 (de)	2000-10-10	2001-10-08	Prozess zur herstellung von r(+)alpha-liponsäure
KR1020037004733A KR100838922B1 (ko)	2000-10-10	2001-10-08	알플러스알파-리포산의 제조 방법
ES01986685T ES2254522T3 (es)	2000-10-10	2001-10-08	Procedimiento de produccion de acido r(+) alfa-lipoico.
CZ20031006A CZ302932B6 (cs)	2000-10-10	2001-10-08	Zpusob výroby R(+)alfa-lipoové kyseliny
EP01986685A EP1330450B1 (en)	2000-10-10	2001-10-08	Process for the production of r(+)alpha-lipoic acid
AU2002223603A AU2002223603A1 (en)	2000-10-10	2001-10-08	Process for the production of r(+)alpha-lipoic acid
JP2002534304A JP4257573B2 (ja)	2000-10-10	2001-10-08	Ｒ（＋）α−リポ酸の製造方法
PCT/EP2001/011575 WO2002030918A2 (en)	2000-10-10	2001-10-08	PROCESS FOR THE PRODUCTION OF R(+)α-LIPOIC ACID
AT01986685T ATE316082T1 (de)	2000-10-10	2001-10-08	Prozess zur herstellung von r(+)alpha-liponsäure
US10/398,892 US6670484B2 (en)	2000-10-10	2001-10-08	Process for the production of r(+)α-lipoic acid

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT2000MI002187A IT1319195B1 (it)	2000-10-10	2000-10-10	Processo per la produzione dell'acido r(+)alfa-lipoico.

Publications (3)

Publication Number	Publication Date
ITMI20002187A0 ITMI20002187A0 (it)	2000-10-10
ITMI20002187A1 ITMI20002187A1 (it)	2002-04-10
IT1319195B1 true IT1319195B1 (it)	2003-09-26

Family

ID=11445936

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IT2000MI002187A IT1319195B1 (it)	2000-10-10	2000-10-10	Processo per la produzione dell'acido r(+)alfa-lipoico.

Country Status (11)

Country	Link
US (1)	US6670484B2 (it)
EP (1)	EP1330450B1 (it)
JP (1)	JP4257573B2 (it)
KR (1)	KR100838922B1 (it)
AT (1)	ATE316082T1 (it)
AU (1)	AU2002223603A1 (it)
CZ (1)	CZ302932B6 (it)
DE (1)	DE60116796T2 (it)
ES (1)	ES2254522T3 (it)
IT (1)	IT1319195B1 (it)
WO (1)	WO2002030918A2 (it)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1319196B1 (it) *	2000-10-10	2003-09-26	Laboratorio Chimico Int Spa	Sintesi dell'acido r(+)alfa-lipoico.
DE10137381A1 (de) *	2001-07-31	2003-02-13	Viatris Gmbh	Neue Modifikationen des Trometamolsalzes der R-Thioctsäure sowie Verfahren zu ihrer Herstellung
ITMI20030831A1 (it)	2003-04-22	2004-10-23	Laboratorio Chimico Int Spa	Sale basico dell'acido tiottico con la l-carnitina.
ITMI20061024A1 (it)	2006-05-25	2007-11-26	Eurand Pharmaceuticals Ltd	Pellet a base di acido lipoico
WO2010047717A1 (en) *	2008-10-24	2010-04-29	Biolink Life Sciences, Inc.	Stable, water-insoluble r-(+)-alpha-lipoic acid salt useful for the treatment of diabetes mellitus and its co-morbidities
CN106959348A (zh) *	2017-05-12	2017-07-18	苏州富士莱医药股份有限公司	一种(r)‑硫辛酸的光学异构体含量的检测方法
CN108003134A (zh) *	2018-01-19	2018-05-08	华东师范大学	一种r-（+）-硫辛酸的制备方法
CN112390779B (zh) *	2019-08-16	2022-09-06	南京海润医药有限公司	一种右旋硫辛酸的制备方法
CN114163418A (zh) *	2021-12-24	2022-03-11	山东龙辰药业有限公司	一种右旋硫辛酸的合成方法

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1374015A (en) *	1920-08-17	1921-04-05	Jerruss Joseph	Safety lock-bolt
US1413024A (en) *	1920-12-04	1922-04-18	Annie L Harrell	Lock nut and bolt
US2456234A (en) *	1945-06-20	1948-12-14	Panhandle Eastern Pipe Line Co	Bolt protector
US2728895A (en) *	1954-10-04	1955-12-27	Whitney Blake Co	Self-locking coupling device
US2966187A (en) *	1958-10-14	1960-12-27	Cock Chars Ter	Pawl and ratchet bolt and nut lock
FR4630M (it) *	1965-06-09	1966-11-28
US3670795A (en) *	1970-06-29	1972-06-20	Wright Barry Corp	Self-locking fastener
US3877672A (en) *	1972-06-21	1975-04-15	Trw Inc	Fastener
US4784555A (en) *	1985-09-09	1988-11-15	Cantrell Roger M	Protective and ornamental cover for nuts and bolts
US4875819A (en) *	1988-10-11	1989-10-24	Kevin Wilkinson	Wheel lock system apparatus
US5042880A (en) *	1990-04-10	1991-08-27	Garuti Raymond R	Quick change wheel assembly
DE4137773A1 (de)	1991-11-16	1993-05-19	Degussa	Herstellung und verwendung von salzen der reinen enantiomere der (alpha)-liponsaeure
US5360304A (en) *	1993-05-11	1994-11-01	Mcgard, Inc.	Fastener construction
US5380070A (en) *	1993-08-09	1995-01-10	Wheel Masters, Inc.	Lug nut covers
US5463093A (en) *	1993-11-26	1995-10-31	Garnett; Merrill	Palladium complexes and methods for using same in the treatment of tumors or Psoriasis
DE4427079C2 (de)	1994-07-30	2002-12-19	Viatris Gmbh	Verfahren zur Racemisierung von Enantiomeren der alpha-Liponsäure
DE4433764A1 (de)	1994-09-22	1996-03-28	Asta Medica Ag	Darreichungsformen enthaltend alpha-Liponsäure, feste Salze von R-Thioctsäure mit verbesserter Freisetzung und Bioverfügbarkeit
AU728488B2 (en) *	1997-04-02	2001-01-11	Sankyo Company Limited	Dithiolan derivatives, their preparation and their therapeutic effect
FR2768055A1 (fr) *	1997-09-11	1999-03-12	Synthelabo	Utilisation de derives de sulfonanilide pour obtenir un medicament destine au traitement de l'ejaculation retrograde ou de l'aspermie
US5965618A (en) *	1997-11-17	1999-10-12	Perricone; Nicholas V.	Treatment of scar tissue using lipoic acid
US6146070A (en) *	1998-03-09	2000-11-14	Mts Co. Ltd.	Bolt/nut unfastening preventing structure
DE19834608A1 (de) *	1998-07-31	2000-02-03	Basf Ag	Kristallmodifikation der Liponsäure
DE19938621A1 (de) *	1999-08-14	2001-02-22	Sueddeutsche Kalkstickstoff	Verfahren zur Herstellung von lösemittelfreier alpha-Liponsäure
US6036420A (en) *	1999-09-21	2000-03-14	Horizon Technology, Llp	Capped wheel nut assembly

2000
- 2000-10-10 IT IT2000MI002187A patent/IT1319195B1/it active
2001
- 2001-10-08 KR KR1020037004733A patent/KR100838922B1/ko not_active IP Right Cessation
- 2001-10-08 ES ES01986685T patent/ES2254522T3/es not_active Expired - Lifetime
- 2001-10-08 EP EP01986685A patent/EP1330450B1/en not_active Expired - Lifetime
- 2001-10-08 CZ CZ20031006A patent/CZ302932B6/cs not_active IP Right Cessation
- 2001-10-08 AT AT01986685T patent/ATE316082T1/de not_active IP Right Cessation
- 2001-10-08 DE DE60116796T patent/DE60116796T2/de not_active Expired - Lifetime
- 2001-10-08 US US10/398,892 patent/US6670484B2/en not_active Expired - Lifetime
- 2001-10-08 AU AU2002223603A patent/AU2002223603A1/en not_active Abandoned
- 2001-10-08 JP JP2002534304A patent/JP4257573B2/ja not_active Expired - Fee Related
- 2001-10-08 WO PCT/EP2001/011575 patent/WO2002030918A2/en active IP Right Grant

Also Published As

Publication number	Publication date
WO2002030918A3 (en)	2002-08-01
US6670484B2 (en)	2003-12-30
AU2002223603A1 (en)	2002-04-22
KR20030070000A (ko)	2003-08-27
DE60116796D1 (de)	2006-04-06
ES2254522T3 (es)	2006-06-16
EP1330450A2 (en)	2003-07-30
ITMI20002187A1 (it)	2002-04-10
WO2002030918A2 (en)	2002-04-18
JP4257573B2 (ja)	2009-04-22
CZ302932B6 (cs)	2012-01-18
ITMI20002187A0 (it)	2000-10-10
EP1330450B1 (en)	2006-01-18
DE60116796T2 (de)	2006-11-30
KR100838922B1 (ko)	2008-06-16
US20030187279A1 (en)	2003-10-02
JP2004511476A (ja)	2004-04-15
ATE316082T1 (de)	2006-02-15

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