NO329558B1 - Anvendelse av benzazepin-N-eddiksyrederivater til fremstilling av farmasoytiske preparater for profylakse og/eller hjelpebehandling av hjerteskader, samt produkter som kombinasjonspreparater som inneholder slike forbindelser - Google Patents

Anvendelse av benzazepin-N-eddiksyrederivater til fremstilling av farmasoytiske preparater for profylakse og/eller hjelpebehandling av hjerteskader, samt produkter som kombinasjonspreparater som inneholder slike forbindelser Download PDF

Info

Publication number: NO329558B1
Authority: NO; Norway
Prior art keywords: group; compounds; formula; cardiotoxic; alkyl
Prior art date: 1999-07-13

Application number

NO20020132A

Other languages

English (en)

Norwegian (no)

Other versions

NO20020132D0 (no

NO20020132L (no

Inventor

Dirk Thormahlen

Harald Waldeck

Julius Gy Papp

Susanna Rozsa

Original Assignee

Solvay Pharm Gmbh

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.)

1999-07-13

Filing date

2002-01-11

Publication date

2010-11-15

2002-01-11 Application filed by Solvay Pharm Gmbh filed Critical Solvay Pharm Gmbh

2002-01-11 Publication of NO20020132D0 publication Critical patent/NO20020132D0/no

2002-03-12 Publication of NO20020132L publication Critical patent/NO20020132L/no

2010-11-15 Publication of NO329558B1 publication Critical patent/NO329558B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 33
238000011282 treatment Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 12
239000000825 pharmaceutical preparation Substances 0.000 title claims description 10
238000011321 prophylaxis Methods 0.000 title claims description 8
230000003683 cardiac damage Effects 0.000 title claims description 6
NTQSYIWTDXTRGG-UHFFFAOYSA-N 2-(1-benzazepin-1-yl)acetic acid Chemical class OC(=O)CN1C=CC=CC2=CC=CC=C12 NTQSYIWTDXTRGG-UHFFFAOYSA-N 0.000 title description 5
239000000824 cytostatic agent Substances 0.000 claims description 29
230000001451 cardiotoxic effect Effects 0.000 claims description 19
230000000694 effects Effects 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 18
231100000457 cardiotoxic Toxicity 0.000 claims description 17
230000001085 cytostatic effect Effects 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
239000003242 anti bacterial agent Substances 0.000 claims description 8
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229940045799 anthracyclines and related substance Drugs 0.000 claims description 7
230000003115 biocidal effect Effects 0.000 claims description 7
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229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
238000002560 therapeutic procedure Methods 0.000 claims description 6
MWWSFMDVAYGXBV-MYPASOLCSA-N (7r,9s)-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.O([C@@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-MYPASOLCSA-N 0.000 claims description 5
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
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125000002947 alkylene group Chemical group 0.000 description 3
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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125000000217 alkyl group Chemical group 0.000 description 2
229940087168 alpha tocopherol Drugs 0.000 description 2
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150000001991 dicarboxylic acids Chemical class 0.000 description 2
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210000005003 heart tissue Anatomy 0.000 description 2
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239000000203 mixture Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
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125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
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WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
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229910052708 sodium Inorganic materials 0.000 description 1
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure

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Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Immunology (AREA)
Heart & Thoracic Surgery (AREA)
Toxicology (AREA)
Molecular Biology (AREA)
Hospice & Palliative Care (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Neurology (AREA)
Biochemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO20020132A 1999-07-13 2002-01-11 Anvendelse av benzazepin-N-eddiksyrederivater til fremstilling av farmasoytiske preparater for profylakse og/eller hjelpebehandling av hjerteskader, samt produkter som kombinasjonspreparater som inneholder slike forbindelser NO329558B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19932555A DE19932555A1 (de)	1999-07-13	1999-07-13	Arzneimittel mit protektiver Wirkung gegen oxidativ-toxische und insbesondere gegen kardiotoxische Substanzen
PCT/EP2000/006525 WO2001003699A1 (de)	1999-07-13	2000-07-10	Arzneimittel mit protektiver wirkung gegen oxidativ-toxische und insbesondere gegen kardiotoxische substanzen

Publications (3)

Publication Number	Publication Date
NO20020132D0 NO20020132D0 (no)	2002-01-11
NO20020132L NO20020132L (no)	2002-03-12
NO329558B1 true NO329558B1 (no)	2010-11-15

Family

ID=7914519

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20020132A NO329558B1 (no)	1999-07-13	2002-01-11	Anvendelse av benzazepin-N-eddiksyrederivater til fremstilling av farmasoytiske preparater for profylakse og/eller hjelpebehandling av hjerteskader, samt produkter som kombinasjonspreparater som inneholder slike forbindelser

Country Status (28)

Country	Link
US (1)	US6906059B2 (cs)
EP (1)	EP1200095B1 (cs)
JP (1)	JP4824235B2 (cs)
KR (1)	KR100738940B1 (cs)
CN (1)	CN1267099C (cs)
AR (1)	AR024476A1 (cs)
AT (1)	ATE306926T1 (cs)
AU (1)	AU782733B2 (cs)
BR (1)	BR0012442A (cs)
CA (1)	CA2377904C (cs)
CZ (1)	CZ299070B6 (cs)
DE (2)	DE19932555A1 (cs)
DK (1)	DK1200095T3 (cs)
ES (1)	ES2246874T3 (cs)
HK (1)	HK1049116B (cs)
HU (1)	HUP0202424A3 (cs)
IL (2)	IL147604A0 (cs)
MX (1)	MXPA02000411A (cs)
NO (1)	NO329558B1 (cs)
NZ (1)	NZ517130A (cs)
PL (1)	PL198723B1 (cs)
RU (1)	RU2268727C2 (cs)
SK (1)	SK286020B6 (cs)
TR (1)	TR200200053T2 (cs)
TW (1)	TWI280880B (cs)
UA (1)	UA73134C2 (cs)
WO (1)	WO2001003699A1 (cs)
ZA (1)	ZA200200265B (cs)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19932555A1 (de) *	1999-07-13	2001-01-18	Solvay Pharm Gmbh	Arzneimittel mit protektiver Wirkung gegen oxidativ-toxische und insbesondere gegen kardiotoxische Substanzen
SK14102003A3 (sk) *	2001-05-18	2004-08-03	Solvay Pharmaceuticals Gmbh	Použitie zlúčenín s kombinovanou inhibičnou aktivitou k NEP/MP pri príprave liečiv
ES2338538T3 (es) *	2001-09-10	2010-05-10	Tibotec Pharmaceuticals	Metodo para la preparacion de hexahidrofuro(2,3-b)furan-3-ol.
BR0306701A (pt) *	2002-01-16	2004-12-28	Solvay Pharm Bv	Composto, sal do composto, sal de cálcio, método de preparação de um sal, composição farmacêutica, método de preparação de uma composição, e, uso de um sal
AR038681A1 (es) *	2002-02-14	2005-01-26	Solvay Pharm Bv	Formulacion oral de solucion solida de una sustancia activa pobremente soluble en agua
US7452875B2 (en)	2003-09-26	2008-11-18	Solvay Pharmaceuticals Gmbh	Amidomethyl-substituted 1-(carboxyalkyl) cyclopentyl-carbonylamino-benzazepine-N-acetic acid compounds, process and intermediate products for their preparation and pharmaceutical compositions containing them
US7427611B2 (en)	2003-09-26	2008-09-23	Solvay Pharmaceuticals Gmbh	Amidomethyl-substituted 1-(carboxyalkyl)-cyclopentyl-carbonylamino-benzazepine-N-acetic acid compounds, process and intermediate products for their preparation and pharmaceutical compositions containing them
US7262184B2 (en)	2003-09-26	2007-08-28	Solvay Pharmaceuticals Gmbh	Amidomethyl-substituted 1-(carboxyalkyl) cyclopentyl-carbonylamino-benzazepine-N-acetic acid compounds, process and intermediate products for their preparation and pharmaceutical compositions containing them
AR046454A1 (es) *	2003-11-18	2005-12-07	Solvay Pharm Gmbh	Uso de un compuesto de acido benzazepin-n-acetico, composicion farmaceutica, y procedimiento para la produccion de dicha composicion farmaceutica
US20050267072A1 (en) *	2004-05-14	2005-12-01	Solvay Pharmaceuticals Gmbh	Pharmaceutical compositions containing dually acting inhibitors of neutral endopeptidase for the treatment of sexual dysfunction
US20050267124A1 (en) *	2004-05-14	2005-12-01	Solvay Pharmaceuticals Gmbh	Pharmaceutical compositions comprising NEP-inhibitors, inhibitors of the endogenous producing system and PDEV inhibiitors
US20050288272A1 (en) *	2004-06-23	2005-12-29	Solvay Pharmaceuticals Gmbh	Pharmaceutical compositions comprising NEP-inhibitors, inhibitors of the endogenous endothelin producing system and AT1 receptor antagonists
WO2006064016A1 (en)	2004-12-15	2006-06-22	Solvay Pharmaceuticals Gmbh	Pharmaceutical compositions comprising nep-inhibitors, inhibitors of the endogenous endothelin producing system and hmg coa reductase inhibitors
US20060205625A1 (en) *	2005-02-18	2006-09-14	Solvay Pharmaceuticals Gmbh	Pharmaceutical compositions comprising NEP-inhibitors, inhibitors of the endogenous endothelin producing system and diuretics
US8709738B2 (en) *	2006-02-27	2014-04-29	Quintiles Transnational Corporation	Methods for predicting cardiac toxicity
WO2007102171A2 (en) *	2006-03-07	2007-09-13	Panacea Biotec Ltd	Novel salts of 1h-1-benzazepine-1-acetic acid, their preparation and pharmaceutical composition
US20070292503A1 (en) *	2006-06-16	2007-12-20	Gorissen Henricus R	Oral pharmaceutical composition of poorly water-soluble active substance
US20070299054A1 (en) *	2006-06-22	2007-12-27	Rajesh Jain	Oral pharmaceutical composition of a poorly water-soluble active agent

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2850078A1 (de) *	1978-11-18	1980-05-29	Basf Ag	Aminopropanolderivate des 6-hydroxy-2,3,4,5-tetrahydro-1h-1- benzazepin-2-ons
CN1040210C (zh) *	1993-07-21	1998-10-14	山之内制药株式会社	稠合的苯并氮杂䓬衍生物及其药学组合物
DE19510566A1 (de) *	1995-03-23	1996-09-26	Kali Chemie Pharma Gmbh	Benzazepin-, Benzoxazepin- und Benzothiazepin-N-essigsäurederivate sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE19638020A1 (de) *	1996-09-18	1998-03-19	Solvay Pharm Gmbh	Die gastrointestinale Durchblutung fördernde Arzneimittel
AU1146099A (en) *	1997-09-18	1999-04-05	Janssen Pharmaceutica N.V.	Fused imidazole derivatives for improving oral bioavailability of pharmaceuticalagents
DE19906310A1 (de) *	1999-02-16	2000-08-17	Solvay Pharm Gmbh	Arzneimittel zur Behandlung von Bluthochdruck
DE19932555A1 (de) *	1999-07-13	2001-01-18	Solvay Pharm Gmbh	Arzneimittel mit protektiver Wirkung gegen oxidativ-toxische und insbesondere gegen kardiotoxische Substanzen

1999
- 1999-07-13 DE DE19932555A patent/DE19932555A1/de not_active Withdrawn
2000
- 2000-06-23 AR ARP000103183A patent/AR024476A1/es unknown
- 2000-07-05 TW TW089113263A patent/TWI280880B/zh active
- 2000-07-10 ES ES00947960T patent/ES2246874T3/es not_active Expired - Lifetime
- 2000-07-10 RU RU2002102709/15A patent/RU2268727C2/ru not_active IP Right Cessation
- 2000-07-10 SK SK14-2002A patent/SK286020B6/sk not_active IP Right Cessation
- 2000-07-10 EP EP00947960A patent/EP1200095B1/de not_active Expired - Lifetime
- 2000-07-10 JP JP2001508979A patent/JP4824235B2/ja not_active Expired - Fee Related
- 2000-07-10 AT AT00947960T patent/ATE306926T1/de active
- 2000-07-10 DE DE50011388T patent/DE50011388D1/de not_active Expired - Lifetime
- 2000-07-10 PL PL353012A patent/PL198723B1/pl not_active IP Right Cessation
- 2000-07-10 CZ CZ20020052A patent/CZ299070B6/cs not_active IP Right Cessation
- 2000-07-10 KR KR1020027000361A patent/KR100738940B1/ko not_active Expired - Fee Related
- 2000-07-10 CA CA002377904A patent/CA2377904C/en not_active Expired - Fee Related
- 2000-07-10 MX MXPA02000411A patent/MXPA02000411A/es active IP Right Grant
- 2000-07-10 HU HU0202424A patent/HUP0202424A3/hu not_active Application Discontinuation
- 2000-07-10 TR TR2002/00053T patent/TR200200053T2/xx unknown
- 2000-07-10 BR BR0012442-7A patent/BR0012442A/pt not_active Application Discontinuation
- 2000-07-10 AU AU61572/00A patent/AU782733B2/en not_active Ceased
- 2000-07-10 IL IL14760400A patent/IL147604A0/xx active IP Right Grant
- 2000-07-10 DK DK00947960T patent/DK1200095T3/da active
- 2000-07-10 WO PCT/EP2000/006525 patent/WO2001003699A1/de not_active Ceased
- 2000-07-10 NZ NZ517130A patent/NZ517130A/en not_active IP Right Cessation
- 2000-07-10 HK HK03101159.2A patent/HK1049116B/zh not_active IP Right Cessation
- 2000-07-10 CN CNB008102015A patent/CN1267099C/zh not_active Expired - Fee Related
- 2000-10-07 UA UA2002021058A patent/UA73134C2/uk unknown
2002
- 2002-01-11 ZA ZA200200265A patent/ZA200200265B/xx unknown
- 2002-01-11 NO NO20020132A patent/NO329558B1/no not_active IP Right Cessation
- 2002-01-13 IL IL147604A patent/IL147604A/en not_active IP Right Cessation
- 2002-01-14 US US10/043,268 patent/US6906059B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU6157200A (en)	2001-01-30
IL147604A (en)	2006-12-31
BR0012442A (pt)	2002-04-02
ZA200200265B (en)	2003-03-26
CZ200252A3 (cs)	2002-08-14
HUP0202424A3 (en)	2003-03-28
PL198723B1 (pl)	2008-07-31
CA2377904C (en)	2009-03-24
NO20020132D0 (no)	2002-01-11
EP1200095A1 (de)	2002-05-02
HK1049116A1 (en)	2003-05-02
KR20020019514A (ko)	2002-03-12
CN1373666A (zh)	2002-10-09
SK286020B6 (sk)	2008-01-07
NZ517130A (en)	2004-10-29
DE19932555A1 (de)	2001-01-18
CZ299070B6 (cs)	2008-04-16
WO2001003699A1 (de)	2001-01-18
IL147604A0 (en)	2002-08-14
RU2268727C2 (ru)	2006-01-27
TWI280880B (en)	2007-05-11
AR024476A1 (es)	2002-10-02
NO20020132L (no)	2002-03-12
SK142002A3 (en)	2002-06-04
ATE306926T1 (de)	2005-11-15
KR100738940B1 (ko)	2007-07-12
DK1200095T3 (da)	2005-11-14
PL353012A1 (en)	2003-10-06
CA2377904A1 (en)	2001-01-18
TR200200053T2 (tr)	2002-05-21
CN1267099C (zh)	2006-08-02
US6906059B2 (en)	2005-06-14
ES2246874T3 (es)	2006-03-01
DE50011388D1 (de)	2006-03-02
US20030040512A1 (en)	2003-02-27
MXPA02000411A (es)	2002-07-02
JP4824235B2 (ja)	2011-11-30
UA73134C2 (en)	2005-06-15
HUP0202424A2 (hu)	2002-11-28
HK1049116B (zh)	2006-12-08
JP2003504336A (ja)	2003-02-04
EP1200095B1 (de)	2005-10-19
AU782733B2 (en)	2005-08-25

Legal Events

Date	Code	Title	Description
2013-03-11	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
RU2268727C2 (ru)	2006-01-27	Лекарственное средство, обладающее защитным действием в отношении окислительно-токсических и прежде всего кардиотоксических соединений
KR100200467B1 (ko)	1999-06-15	콜레스테롤 저하제 및 ace 억제제로 이루어진 아테롬성 동맥경화증의 예방, 안정화 또는 경감용 조성물
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CZ301499B6 (cs)	2010-03-24	Lék pro lécbu vysokého krevního tlaku
WO2009117367A1 (en)	2009-09-24	Method for treating cancers having high glucose requirements employing an sglt2 inhibitor and compositions thereof
US4469690A (en)	1984-09-04	Synergistic compositions of renal dopaminergic agent and β-blocker
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EP1906972B1 (en)	2013-09-11	LPA2 receptor agonist for treating diarrhea
US9029334B2 (en)	2015-05-12	Pharmaceutical composition for prevention or treatment of bone diseases comprising spinasterol glucoside derivative
US8518895B2 (en)	2013-08-27	Method for treating hyponatremia employing an SGLT2 inhibitor and composition containing same
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WO2013137382A1 (ja)	2013-09-19	骨代謝改善剤
David	2003	Oxcarbazepine, Top&mate, Zonisamide, and Levetiracetam: Potential Use in Neuropathic Pain
HUT52384A (en)	1990-07-28	Process for producing pharmaceutical compositions comprising dianhydrohexitol acyl derivatives
IE54373B1 (en)	1989-09-13	Pharmaceutical compositions comprising, 7,8-dihydroxy-1(hydroxyphenyl)-2,3,4,5-tetrahydro-ih-3-benzanepine derivatives and a beta-adrenergic blocking compound
HK1113906A (en)	2008-10-17	Pharmaceutical compositions comprising nep-inhibitors, inhibitors of the endogenous endothelin producing system and diuretics