NO317178B1 - Anvendelse av (+) norcisaprid for fremstilling av medikamenter samt farmasoytisk preparat og enhetsdoseform omfattende forbindelsen - Google Patents

Anvendelse av (+) norcisaprid for fremstilling av medikamenter samt farmasoytisk preparat og enhetsdoseform omfattende forbindelsen Download PDF

Info

Publication number: NO317178B1
Authority: NO; Norway
Prior art keywords: norcisapride; pharmaceutically acceptable; use according; acceptable salt; per day
Prior art date: 1996-07-19

Application number

NO19983636A

Other languages

English (en)

Norwegian (no)

Other versions

NO983636D0 (no

NO983636L (no

Inventor

Thomas P Jerussi

John R Mccullough

Original Assignee

Sepracor Inc

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.)

1996-07-19

Filing date

1998-08-07

Publication date

2004-09-06

1998-08-07 Application filed by Sepracor Inc filed Critical Sepracor Inc

1998-08-07 Publication of NO983636D0 publication Critical patent/NO983636D0/no

1998-10-19 Publication of NO983636L publication Critical patent/NO983636L/no

2004-09-06 Publication of NO317178B1 publication Critical patent/NO317178B1/no

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CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 1
229950010357 tetrodotoxin Drugs 0.000 description 1
CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
229960001005 tuberculin Drugs 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
230000001515 vagal effect Effects 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
229960002555 zidovudine Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4468—Non condensed piperidines, e.g. piperocaine having a nitrogen directly attached in position 4, e.g. clebopride, fentanyl
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Epidemiology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Psychology (AREA)
Otolaryngology (AREA)
Nutrition Science (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO19983636A 1996-07-19 1998-08-07 Anvendelse av (+) norcisaprid for fremstilling av medikamenter samt farmasoytisk preparat og enhetsdoseform omfattende forbindelsen NO317178B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/684,753 US5739151A (en)	1996-07-19	1996-07-19	Method for treating emesis and central nervous system disorders using optically pure (+) norcisapride
PCT/US1997/011629 WO1998003173A1 (en)	1996-07-19	1997-07-02	Methods for treating emesis and central nervous system disorders using optically pure (+) norcisapride

Publications (3)

Publication Number	Publication Date
NO983636D0 NO983636D0 (no)	1998-08-07
NO983636L NO983636L (no)	1998-10-19
NO317178B1 true NO317178B1 (no)	2004-09-06

Family

ID=24749413

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO19983636A NO317178B1 (no)	1996-07-19	1998-08-07	Anvendelse av (+) norcisaprid for fremstilling av medikamenter samt farmasoytisk preparat og enhetsdoseform omfattende forbindelsen
NO20041166A NO20041166L (no)	1996-07-19	2004-03-19	Anvendelse av optisk rent (+) norcisaprid sammen med et annet terapeutisk middel for fremstilling av et medikament

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO20041166A NO20041166L (no)	1996-07-19	2004-03-19	Anvendelse av optisk rent (+) norcisaprid sammen med et annet terapeutisk middel for fremstilling av et medikament

Country Status (25)

Country	Link
US (3)	US5739151A (de)
EP (1)	EP0896539B1 (de)
JP (1)	JP3097697B2 (de)
KR (4)	KR100328731B1 (de)
CN (1)	CN1215992A (de)
AT (1)	ATE197762T1 (de)
AU (1)	AU3592097A (de)
BG (1)	BG63190B1 (de)
BR (1)	BR9708287A (de)
CA (1)	CA2245768C (de)
CZ (1)	CZ293478B6 (de)
DE (1)	DE69703617T2 (de)
DK (1)	DK0896539T3 (de)
ES (1)	ES2152687T3 (de)
GR (1)	GR3035460T3 (de)
HU (1)	HUP9904360A3 (de)
IL (1)	IL125703A0 (de)
IS (1)	IS4820A (de)
NO (2)	NO317178B1 (de)
NZ (1)	NZ331291A (de)
PL (1)	PL189610B1 (de)
PT (1)	PT896539E (de)
SK (1)	SK282673B6 (de)
TR (1)	TR199801816T2 (de)
WO (1)	WO1998003173A1 (de)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5712293A (en) *	1995-06-07	1998-01-27	Sepracor, Inc.	Methods for treating gastro-esophageal reflux disease and other disorders associated with the digestive tract using optically pure (-) norcisapride
US5739151A (en) *	1996-07-19	1998-04-14	Sepracor Inc.	Method for treating emesis and central nervous system disorders using optically pure (+) norcisapride
US6147093A (en)	1996-07-19	2000-11-14	Sepracor Inc.	Methods for treating gastroesophageal reflux disease
JP2001501960A (ja) *	1996-10-15	2001-02-13	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	シサプリドの合成
CN1196681C (zh)	1997-07-11	2005-04-13	詹森药业有限公司	(+)诺西沙必利用于制备5－ht3和5ht4 介导的疾病的药物中的用途
JP2003522103A (ja)	1998-06-15	2003-07-22	セプラコアインコーポレーテッド	無呼吸、過食症およびその他の障害を治療するための光学的に純粋な（−）−ノルシスアプリドの使用
EP1464333A3 (de) *	1998-06-15	2004-12-15	Sepracor Inc.	Verwendung von optisch reines (-) Norcisapride in der Behandlung von Apnea, Bulimia und andere Krankheiten
EP1468685A3 (de) *	1998-06-15	2004-12-15	Sepracor Inc.	Verwendung von optisch reines (+)-Norcisapride für die Behandlung von Apnea, Bulimia und andere Krankheiten
TR200103057T2 (tr)	1998-06-15	2002-06-21	Sepracor Inc.	Apne, bulimi ve başka bozuklukların tedavi edilmesi için optik açıdan saf (+)-norsisapridin kullanımı
ES2257869T3 (es) *	1998-08-21	2006-08-01	Novartis Ag	Nueva formulacion oral para agonistas o antagonistas de 5-ht4.
US6362202B1 (en) *	1999-03-02	2002-03-26	Sepracor Inc.	Methods and compositions using (−) norcisapride in combination with proton pump inhibitors or H2 receptor antagonists
US6353005B1 (en) *	1999-03-02	2002-03-05	Sepracor, Inc.	Method and compositions using (+) norcisapride in combination with proton pump inhibitors or H2 receptor antagonist
US6803387B1 (en) *	1999-03-19	2004-10-12	Abbott Gmbh & Co. Kg	Treatment of neuropathic pain or fibromyalgia
US20020013327A1 (en) *	2000-04-18	2002-01-31	Lee Andrew G.	Compositions and methods for treating female sexual dysfunction
EP1321142A1 (de) *	2001-12-21	2003-06-25	Novartis AG	Feste orale Zubereitung mit Tegaserod
FR2854072B1 (fr) *	2003-04-23	2006-08-04	Centre Nat Rech Scient	Vecteur pour administration par voie orale
US8524736B2 (en)	2004-01-07	2013-09-03	Armetheon, Inc.	Stereoisomeric compounds and methods for the treatment of gastrointestinal and central nervous system disorders
US8138204B2 (en) *	2004-01-07	2012-03-20	Aryx Therapeutics, Inc.	Stereoisomeric compounds and methods for the treatment of gastrointestinal and central nervous system disorders
RU2374244C2 (ru)	2004-01-07	2009-11-27	Арикс Терапьютикс	Стереоизомерные соединения и способы лечения желудочно-кишечных расстройств и расстройств центральной нервной системы
US20090170899A1 (en) *	2004-09-14	2009-07-02	Guy Debonnel	Stimulators of 5-HT4 receptors and uses thereof
AU2006284601B2 (en) *	2005-08-31	2012-12-20	Renexxion, Llc	Synthetic methods and intermediates for stereoisomeric compounds useful for the treatment of gastrointestinal and central nervous system disorders
WO2007149929A1 (en) *	2006-06-23	2007-12-27	Aryx Therapeutics, Inc.	Piperidine derivatives for the treatment of gastrointestinal and cns disorders
EP2488171A4 (de)	2009-10-16	2014-04-23	Epiomed Therapeutics Inc	Behandlung von erbrechen
BR112013020641B1 (pt) *	2011-02-25	2021-11-03	Yuhan Corporation	Composto, composição farmacêutica, processos para a preparação de composto e respectivo uso ou de seu sal farmaceuticamente aceitável

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5057525A (en) *	1981-10-01	1991-10-15	Janssen Pharmaceutica N.V.	Novel N-(3-hydroxy-4-piperidinyl) benzamide derivatives
US5137896A (en) *	1981-10-01	1992-08-11	Janssen Pharmaceutica N.V.	N-(3-hydroxy-4-piperidinyl)benzamide derivatives
US4962115A (en) *	1981-10-01	1990-10-09	Janssen Pharmaceutica N.V.	Novel N-(3-hydroxy-4-piperidinyl)benzamide derivatives
CA1183847A (en) *	1981-10-01	1985-03-12	Georges Van Daele	N-(3-hydroxy-4-piperidinyl)benzamide derivatives
US5114715A (en) *	1990-11-29	1992-05-19	Sepracor Inc.	Methods of use and compositions of (s)-isoflurane and (s)-desflurane
US5114714A (en) *	1990-11-29	1992-05-19	Sepracor, Inc.	Methods of use and compositions of (r)-isoflurane and (r)-desflurane
WO1994001111A1 (en) *	1992-07-07	1994-01-20	Sepracor Inc.	Methods of using (+) cisapride for the treatment of gastro-esophageal reflux disease and other disorders
EP1145715A3 (de) *	1992-07-07	2004-05-19	Sepracor Inc.	Verfahren zur Verwendung von (-) Cisapride zur Behandlung von Magenspeiseroehrenruechstornung und anderen Erkrankungen
EP0707492A1 (de) *	1993-07-06	1996-04-24	Merck & Co. Inc.	Kombinationen aus h 2? antagonisten und gastrointestinalen motilitässubstanzen
US5712293A (en) *	1995-06-07	1998-01-27	Sepracor, Inc.	Methods for treating gastro-esophageal reflux disease and other disorders associated with the digestive tract using optically pure (-) norcisapride
US5739151A (en) *	1996-07-19	1998-04-14	Sepracor Inc.	Method for treating emesis and central nervous system disorders using optically pure (+) norcisapride

1996
- 1996-07-19 US US08/684,753 patent/US5739151A/en not_active Expired - Fee Related
1997
- 1997-07-02 PT PT97932467T patent/PT896539E/pt unknown
- 1997-07-02 NZ NZ331291A patent/NZ331291A/en unknown
- 1997-07-02 KR KR1019980706152A patent/KR100328731B1/ko not_active Expired - Fee Related
- 1997-07-02 PL PL97335254A patent/PL189610B1/pl not_active IP Right Cessation
- 1997-07-02 KR KR10-2003-7013889A patent/KR100533237B1/ko not_active Expired - Fee Related
- 1997-07-02 SK SK1239-98A patent/SK282673B6/sk unknown
- 1997-07-02 WO PCT/US1997/011629 patent/WO1998003173A1/en not_active Ceased
- 1997-07-02 KR KR10-2001-7011625A patent/KR100422492B1/ko not_active Expired - Fee Related
- 1997-07-02 BR BR9708287-2A patent/BR9708287A/pt not_active Application Discontinuation
- 1997-07-02 DE DE69703617T patent/DE69703617T2/de not_active Expired - Fee Related
- 1997-07-02 AT AT97932467T patent/ATE197762T1/de not_active IP Right Cessation
- 1997-07-02 HU HU9904360A patent/HUP9904360A3/hu unknown
- 1997-07-02 ES ES97932467T patent/ES2152687T3/es not_active Expired - Lifetime
- 1997-07-02 CZ CZ19982508A patent/CZ293478B6/cs not_active IP Right Cessation
- 1997-07-02 AU AU35920/97A patent/AU3592097A/en not_active Abandoned
- 1997-07-02 EP EP97932467A patent/EP0896539B1/de not_active Expired - Lifetime
- 1997-07-02 CA CA002245768A patent/CA2245768C/en not_active Expired - Fee Related
- 1997-07-02 DK DK97932467T patent/DK0896539T3/da active
- 1997-07-02 CN CN97192157A patent/CN1215992A/zh active Pending
- 1997-07-02 KR KR10-2001-7011626A patent/KR100399808B1/ko not_active Expired - Fee Related
- 1997-07-02 IL IL12570397A patent/IL125703A0/xx unknown
- 1997-07-02 JP JP10506954A patent/JP3097697B2/ja not_active Expired - Fee Related
- 1997-07-02 TR TR1998/01816T patent/TR199801816T2/xx unknown
- 1997-08-05 US US08/905,941 patent/US5877188A/en not_active Expired - Fee Related
1998
- 1998-07-13 US US09/114,319 patent/US6114356A/en not_active Expired - Fee Related
- 1998-08-07 NO NO19983636A patent/NO317178B1/no unknown
- 1998-08-10 IS IS4820A patent/IS4820A/is unknown
- 1998-09-09 BG BG102757A patent/BG63190B1/bg unknown
2001
- 2001-02-22 GR GR20010400294T patent/GR3035460T3/el not_active IP Right Cessation
2004
- 2004-03-19 NO NO20041166A patent/NO20041166L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
BG63190B1 (bg)	2001-06-29
HUP9904360A3 (en)	2001-07-30
CZ293478B6 (cs)	2004-05-12
BR9708287A (pt)	2000-01-18
KR100533237B1 (ko)	2005-12-05
GR3035460T3 (en)	2001-05-31
WO1998003173A1 (en)	1998-01-29
KR20040007505A (ko)	2004-01-24
DE69703617T2 (de)	2001-04-12
IS4820A (is)	1998-08-10
KR100422492B1 (ko)	2004-03-11
SK282673B6 (sk)	2002-11-06
PT896539E (pt)	2001-05-31
ES2152687T3 (es)	2001-02-01
US6114356A (en)	2000-09-05
BG102757A (en)	1999-08-31
CZ250898A3 (cs)	1999-04-14
KR100399808B1 (ko)	2003-09-29
NO983636D0 (no)	1998-08-07
NZ331291A (en)	2000-06-23
HUP9904360A2 (hu)	2000-05-28
JP3097697B2 (ja)	2000-10-10
CA2245768A1 (en)	1998-01-29
CA2245768C (en)	2003-09-30
US5877188A (en)	1999-03-02
TR199801816T2 (xx)	2000-10-23
DK0896539T3 (da)	2001-02-19
DE69703617D1 (de)	2001-01-04
PL189610B1 (pl)	2005-08-31
IL125703A0 (en)	1999-04-11
JPH11510828A (ja)	1999-09-21
PL335254A1 (en)	2000-04-10
CN1215992A (zh)	1999-05-05
EP0896539A1 (de)	1999-02-17
KR100328731B1 (ko)	2002-10-19
US5739151A (en)	1998-04-14
SK123998A3 (en)	1999-03-12
ATE197762T1 (de)	2000-12-15
NO983636L (no)	1998-10-19
AU3592097A (en)	1998-02-10
KR20000064524A (ko)	2000-11-06
NO20041166L (no)	2004-03-19
EP0896539B1 (de)	2000-11-29

Publication	Publication Date	Title
NO317178B1 (no)	2004-09-06	Anvendelse av (+) norcisaprid for fremstilling av medikamenter samt farmasoytisk preparat og enhetsdoseform omfattende forbindelsen
EP1462104B1 (de)	2007-01-24	Optisch reines (-) norcisaprid zur Behandlung von Krankheiten des Verdauungstraktes
US6147093A (en)	2000-11-14	Methods for treating gastroesophageal reflux disease
AU780107B2 (en)	2005-03-03	Methods for treating emesis and central nervous system disorders using optically pure () norcisapride
MXPA01000919A (en)	2002-03-26	Methods and compositions for treating gastro-esophageal reflux disease
AU2004200165A1 (en)	2004-02-12	Methods and compositions for treating gastro-esophageal reflux disease