IL119400A - Process for the preparation of enantiomerically pure imidazolyl compounds such as cilansetron by optical resolution with pyroglutamic acid - Google Patents

Process for the preparation of enantiomerically pure imidazolyl compounds such as cilansetron by optical resolution with pyroglutamic acid

Info

Publication number: IL119400A
Authority: IL; Israel
Prior art keywords: addition salt; acid; mixture; enantiomer; compound
Prior art date: 1995-10-13

Application number

IL11940096A

Other languages

English (en)

Other versions

IL119400A0 (en

Original Assignee

Duphar Int Res

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.)

1995-10-13

Filing date

1996-10-10

Publication date

2000-02-29

1996-10-10 Application filed by Duphar Int Res filed Critical Duphar Int Res

1997-01-10 Publication of IL119400A0 publication Critical patent/IL119400A0/xx

2000-02-29 Publication of IL119400A publication Critical patent/IL119400A/xx

Links

ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 title abstract 3
238000000034 method Methods 0.000 title abstract 3
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 title abstract 2
ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 title abstract 2
NCNFDKWULDWJDS-OAHLLOKOSA-N cilansetron Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C=3N4CCCC=3C=CC=2)=C4CC1 NCNFDKWULDWJDS-OAHLLOKOSA-N 0.000 title 1
229960002099 cilansetron Drugs 0.000 title 1
125000002883 imidazolyl group Chemical group 0.000 title 1
230000003287 optical effect Effects 0.000 title 1
150000003839 salts Chemical class 0.000 abstract 7
239000002253 acid Substances 0.000 abstract 6
239000000203 mixture Substances 0.000 abstract 6
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 4
150000001875 compounds Chemical class 0.000 abstract 3
239000012452 mother liquor Substances 0.000 abstract 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 2
-1 imidazolyl compound Chemical class 0.000 abstract 2
238000000926 separation method Methods 0.000 abstract 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
229910052739 hydrogen Inorganic materials 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Epoxy Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL11940096A 1995-10-13 1996-10-10 Process for the preparation of enantiomerically pure imidazolyl compounds such as cilansetron by optical resolution with pyroglutamic acid IL119400A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP95202765		1995-10-13

Publications (2)

Publication Number	Publication Date
IL119400A0 IL119400A0 (en)	1997-01-10
IL119400A true IL119400A (en)	2000-02-29

Family

ID=8220714

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11940096A IL119400A (en)	1995-10-13	1996-10-10	Process for the preparation of enantiomerically pure imidazolyl compounds such as cilansetron by optical resolution with pyroglutamic acid

Country Status (24)

Country	Link
US (1)	US5663343A (fr)
EP (1)	EP0768309B1 (fr)
JP (2)	JP4590038B2 (fr)
KR (1)	KR100459745B1 (fr)
CN (1)	CN1060774C (fr)
AT (1)	ATE224896T1 (fr)
AU (1)	AU702594B2 (fr)
CA (1)	CA2187484C (fr)
CZ (1)	CZ288042B6 (fr)
DE (1)	DE69623900T2 (fr)
DK (1)	DK0768309T3 (fr)
DZ (1)	DZ2104A1 (fr)
ES (1)	ES2183908T3 (fr)
HK (1)	HK1000446A1 (fr)
HU (1)	HU226620B1 (fr)
IL (1)	IL119400A (fr)
NO (1)	NO307257B1 (fr)
NZ (1)	NZ299562A (fr)
PT (1)	PT768309E (fr)
RU (1)	RU2162085C2 (fr)
SK (1)	SK283471B6 (fr)
TW (1)	TW513423B (fr)
UA (1)	UA48947C2 (fr)
ZA (1)	ZA968525B (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19813661A1 (de) *	1997-08-01	1999-02-04	Solvay Pharm Gmbh	Gegen Racemisierung stabilisierte pharmazeutische Zubereitungen von Cilansetron
US6372919B1 (en) *	2001-01-11	2002-04-16	Dov Pharmaceutical, Inc.	(+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as an anti-depressant agent
RU2213562C2 (ru) *	2001-03-14	2003-10-10	Научно-исследовательский институт фармакологии РАМН	Лекарственная композиция
GB0216027D0 (en) *	2002-07-10	2002-08-21	Arachnova Therapeutics Ltd	New therapeutic use
US20040048874A1 (en) *	2001-05-22	2004-03-11	Bardsley Hazel Judith	New therapeutic use of 4-(2-fluorophenyl)-6-methyl-2-(1-piperazinyl)thieno[2,3-D]pyrimidine
US7015333B2 (en) *	2002-11-18	2006-03-21	Solvay Pharmaceuticals B.V.	Process for preparation of imidazolyl compounds
EP1424337A1 (fr) *	2002-11-26	2004-06-02	Solvay Pharmaceuticals GmbH	Dérivés 4-hydroxy de 5,6,9,10-tetrahydro-10-((2-méthyl-1h-imidazol-1-yl)méthyl)-4h-pyrido-(3,2,1-jk)-carbazol-11(8h)-one
ES2285407T3 (es) *	2003-01-13	2007-11-16	Dynogen Pharmaceuticals Inc.	Metodo para el tratamiento de nauseas, vomitos, arcadas o cualquiera de sus combinaciones.
KR20050111318A (ko) *	2003-01-13	2005-11-24	다이노젠 파마세우티컬스, 인코포레이티드	기능성 장 질환을 치료하는 방법
CA2519379A1 (fr) *	2003-04-04	2004-10-21	Dynogen Pharmaceuticals, Inc.	Methode de traitement de troubles des voies urinaires inferieures
US20090018351A1 (en) *	2003-11-12	2009-01-15	Dr. Reddy's Laboratories, Inc.	Preparation of escitalopram
US20070043100A1 (en)	2005-08-16	2007-02-22	Hagen Eric J	Novel polymorphs of azabicyclohexane
US20080045725A1 (en)	2006-04-28	2008-02-21	Murry Jerry A	Process For The Synthesis of (+) And (-)-1-(3,4-Dichlorophenyl)-3-Azabicyclo[3.1.0]Hexane
US7662831B2 (en)	2006-07-27	2010-02-16	Wyeth Llc	Tetracyclic indoles as potassium channel modulators
US7601856B2 (en)	2006-07-27	2009-10-13	Wyeth	Benzofurans as potassium ion channel modulators
JP5156222B2 (ja) *	2006-11-28	2013-03-06	エムキュアファーマシューティカルズリミテッド	制吐作用化合物の新たな製造方法
GB0910373D0 (en) *	2009-06-16	2009-07-29	Filtrona Int Ltd	Tabacco smoke filter
US9806720B1 (en) *	2016-10-07	2017-10-31	Analog Devices Global	Compound semiconductor based inverter
WO2019222565A1 (fr)	2018-05-18	2019-11-21	Kura Oncology, Inc.	Synthèse de tipifarnib

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7413843A (nl) *	1974-10-23	1976-04-27	Stamicarbon	Optische scheiding van fenylglycine-amide.
US4463176A (en) *	1982-09-13	1984-07-31	Mead Johnson & Company	Process for resolution of optical isomers
US4849527A (en) *	1982-09-13	1989-07-18	Bristol-Myers Company	Process for resolution of optical isomers
PH22672A (en) *	1984-01-25	1988-11-14	Glaxo Group Ltd	Imidazolylmethyltetrahydrocarbazolone derivatives, composition and method of use thereof
DE3885357T2 (de) *	1987-06-29	1994-03-24	Duphar Int Res	Anellierte Indolderivate.
GB8812636D0 (en) *	1988-05-27	1988-06-29	Glaxo Group Ltd	Chemical compounds
US5049563A (en) *	1988-07-07	1991-09-17	Duphar International Research B.V.	Annelated indoleketones with an imidazolylalkyl substituent
DE4238553A1 (de) *	1992-11-14	1994-05-19	Kali Chemie Pharma Gmbh	Neue Imidazol-1-yl-Verbindungen enthaltende Arzneimittel
RU2041876C1 (ru) *	1993-12-29	1995-08-20	Научно-производственный центр "Фармзащита"	Способ получения 1,2,3,9- тетрагидро-9-метил-3- [(2-метил-1н- имидазол-1-ил) метил]-4н- карбазол-4-она или его солей, или их гидратов, и промежуточные продукты для их синтеза

1996
- 1996-09-26 AU AU65856/96A patent/AU702594B2/en not_active Ceased
- 1996-10-03 TW TW085112098A patent/TW513423B/zh not_active IP Right Cessation
- 1996-10-08 JP JP28461296A patent/JP4590038B2/ja not_active Expired - Fee Related
- 1996-10-08 SK SK1287-96A patent/SK283471B6/sk not_active IP Right Cessation
- 1996-10-08 CZ CZ19962947A patent/CZ288042B6/cs not_active IP Right Cessation
- 1996-10-09 CA CA002187484A patent/CA2187484C/fr not_active Expired - Fee Related
- 1996-10-09 ZA ZA968525A patent/ZA968525B/xx unknown
- 1996-10-09 DZ DZ960148A patent/DZ2104A1/fr active
- 1996-10-09 HU HU9602778A patent/HU226620B1/hu not_active IP Right Cessation
- 1996-10-09 RU RU96120366/04A patent/RU2162085C2/ru not_active IP Right Cessation
- 1996-10-09 NO NO964282A patent/NO307257B1/no not_active IP Right Cessation
- 1996-10-10 UA UA96103876A patent/UA48947C2/uk unknown
- 1996-10-10 AT AT96202829T patent/ATE224896T1/de active
- 1996-10-10 IL IL11940096A patent/IL119400A/xx not_active IP Right Cessation
- 1996-10-10 PT PT96202829T patent/PT768309E/pt unknown
- 1996-10-10 EP EP96202829A patent/EP0768309B1/fr not_active Expired - Lifetime
- 1996-10-10 DK DK96202829T patent/DK0768309T3/da active
- 1996-10-10 DE DE69623900T patent/DE69623900T2/de not_active Expired - Lifetime
- 1996-10-10 ES ES96202829T patent/ES2183908T3/es not_active Expired - Lifetime
- 1996-10-10 KR KR1019960044972A patent/KR100459745B1/ko not_active Expired - Fee Related
- 1996-10-10 CN CN96122637A patent/CN1060774C/zh not_active Expired - Fee Related
- 1996-10-10 US US08/728,794 patent/US5663343A/en not_active Expired - Lifetime
- 1996-10-11 NZ NZ299562A patent/NZ299562A/en not_active IP Right Cessation
1997
- 1997-07-19 HK HK97101586A patent/HK1000446A1/en not_active IP Right Cessation
2010
- 2010-04-15 JP JP2010094211A patent/JP2010159292A/ja active Pending

Also Published As

Publication number	Publication date
DZ2104A1 (fr)	2002-07-22
JPH09183779A (ja)	1997-07-15
TW513423B (en)	2002-12-11
US5663343A (en)	1997-09-02
PT768309E (pt)	2003-02-28
DE69623900T2 (de)	2003-07-31
HU9602778D0 (en)	1996-11-28
KR100459745B1 (ko)	2005-01-26
EP0768309A1 (fr)	1997-04-16
CZ294796A3 (en)	1997-05-14
HU226620B1 (en)	2009-04-28
CZ288042B6 (cs)	2001-04-11
JP2010159292A (ja)	2010-07-22
HUP9602778A3 (en)	1997-08-28
ZA968525B (en)	1997-05-20
ATE224896T1 (de)	2002-10-15
CA2187484A1 (fr)	1997-04-14
JP4590038B2 (ja)	2010-12-01
NO964282D0 (no)	1996-10-09
NO964282L (no)	1997-04-14
AU6585696A (en)	1997-04-17
AU702594B2 (en)	1999-02-25
EP0768309B1 (fr)	2002-09-25
SK283471B6 (sk)	2003-08-05
CA2187484C (fr)	2006-09-05
IL119400A0 (en)	1997-01-10
UA48947C2 (uk)	2002-09-16
SK128796A3 (en)	1997-05-07
NO307257B1 (no)	2000-03-06
HUP9602778A2 (en)	1997-05-28
CN1060774C (zh)	2001-01-17
HK1000446A1 (en)	2003-01-10
ES2183908T3 (es)	2003-04-01
KR970021080A (ko)	1997-05-28
RU2162085C2 (ru)	2001-01-20
DE69623900D1 (de)	2002-10-31
NZ299562A (en)	1997-09-22
DK0768309T3 (da)	2002-12-09
CN1160053A (zh)	1997-09-24

Legal Events

Date	Code	Title
2000-06-29	FF	Patent granted
2000-10-31	KB	Patent renewed
2003-01-12	KB	Patent renewed
2006-12-07	KB	Patent renewed
2015-05-31	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
IL119400A0 (en)	1997-01-10	Process for the preparation of enantiomerically pure imidazolyl compounds
US5281722A (en)	1994-01-25	Preparation and use of salts of the pure enantiomers of alpha-lipoic acid
RU96120366A (ru)	1998-12-27	Способ получения энантиомерно чистых соединений имидазолила, энантиомерно чистая кислая аддитивная соль имидазолила и в-пироглутаминовой кислоты
US20090093650A1 (en)	2009-04-09	Resolution of alpha-(phenoxy)phenylacetic acid derivatives with naphthyl-alkylamines
EP0623104B1 (fr)	1997-08-27	Resolution du profene
HU903768D0 (en)	1990-11-28	Process for producing new n-heteroaryl-purine-6-amine derivatives and pharmaceutical preparatives containing such compounds
JP2009108079A (ja)	2009-05-21	エナンチオマーに富むｎ−アシルアゼチジン−２−カルボン酸の製造方法
CA2253711C (fr)	2005-08-23	Procede ameliore permettant de produire de l'acide azetine-2-carboxylique ne contenant pas d'enantiomeres
EP0220435B1 (fr)	1990-11-14	Procédé de préparation de semi-esters optiquement actifs
EP0508133A3 (en)	1993-03-03	Method of preparation of l-carnitine from d,l-carnitine nitrile salts
NO20005259D0 (no)	2000-10-19	FremgangsmÕte for fremstilling av enantiomerrent N-metyl-N- [(1S)-1-fenyl-2-((3S)-3-hydroksypyrrolidin-1-yl)etyl]-2,2- difenylacetamid
FI93833C (fi)	1995-06-12	Menetelmä propionihappojohdosten valmistamiseksi
Schjelderup et al.	1986	The absolute configuration of oxyphencyclimine, a parasympatholytic drug. Syntheses of both enantiomers
US4584313A (en)	1986-04-22	(Substituted-phenyl)-5-oxo-2-pyrrolidinepropanoic acids and esters thereof, and use for reversing electroconvulsive shock-induced amnesia
US6166224A (en)	2000-12-26	Method for racemization of optically active azetidine-2-carboxylate
CA2089626A1 (fr)	1993-08-18	Methode de preparation de (r) et de (s)-1,2-isopropylideneglycerol
ZA969534B (en)	1997-05-30	Preparation of chiral pyrrolidinone derivatives
HU202803B (en)	1991-04-29	Process for separation of optical isomers of m-phenoxymandelic acid