CA2334775A1 - Benzo(b)thiepine-1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use - Google Patents

Benzo(b)thiepine-1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use Download PDF

Info

Publication number
CA2334775A1
CA2334775A1 CA002334775A CA2334775A CA2334775A1 CA 2334775 A1 CA2334775 A1 CA 2334775A1 CA 002334775 A CA002334775 A CA 002334775A CA 2334775 A CA2334775 A CA 2334775A CA 2334775 A1 CA2334775 A1 CA 2334775A1
Authority
CA
Canada
Prior art keywords
compounds
thiepine
benzo
pharmaceuticals
preparation
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002334775A
Other languages
French (fr)
Other versions
CA2334775C (en
Inventor
Wendelin Frick
Alfons Enhsen
Heiner Glombik
Hubert Heuer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis Deutschland GmbH
Original Assignee
Aventis Pharma Deutschland Gmbh
Wendelin Frick
Alfons Enhsen
Heiner Glombik
Hubert Heuer
Sanofi-Aventis Deutschland 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.)
Filing date
Publication date
Application filed by Aventis Pharma Deutschland Gmbh, Wendelin Frick, Alfons Enhsen, Heiner Glombik, Hubert Heuer, Sanofi-Aventis Deutschland Gmbh filed Critical Aventis Pharma Deutschland Gmbh
Publication of CA2334775A1 publication Critical patent/CA2334775A1/en
Application granted granted Critical
Publication of CA2334775C publication Critical patent/CA2334775C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D337/00Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
    • C07D337/02Seven-membered rings
    • C07D337/06Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D337/08Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/38Heterocyclic compounds having sulfur as a ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/04Drugs for disorders of the urinary system for urolithiasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • C07K5/06086Dipeptides with the first amino acid being basic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32Polymers modified by chemical after-treatment
    • C08G65/329Polymers modified by chemical after-treatment with organic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Polymers & Plastics (AREA)
  • Biochemistry (AREA)
  • Obesity (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)

Abstract

The invention relates to substituted benzo(b)thiepine-1,1-dioxide derivatives and to the acid addition salts thereof. The invention relates to compounds of formula (1), wherein R1, R2, R3, R4, R5 and Z have the cited descriptions, to the physiologically compatible salts, to physiologically functional derivatives, and to a method for the production thereof. The compounds are suited, for example, as hypolipidemic agents.
CA002334775A 1998-06-10 1999-05-28 Benzo(b)thiepine-1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use Expired - Fee Related CA2334775C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19825804A DE19825804C2 (en) 1998-06-10 1998-06-10 1,4-Benzothiepin-1,1-dioxide derivatives, processes for their preparation and medicaments containing these compounds
DE19825804.6 1998-06-10
PCT/EP1999/003701 WO1999064410A1 (en) 1998-06-10 1999-05-28 BENZO(b)THIEPINE-1,1-DIOXIDE DERIVATIVES, A METHOD FOR THE PRODUCTION THEREOF, MEDICAMENTS CONTAINING THESE COMPOUNDS, AND THEIR USE

Publications (2)

Publication Number Publication Date
CA2334775A1 true CA2334775A1 (en) 1999-12-16
CA2334775C CA2334775C (en) 2009-10-13

Family

ID=7870440

Family Applications (2)

Application Number Title Priority Date Filing Date
CA002334775A Expired - Fee Related CA2334775C (en) 1998-06-10 1999-05-28 Benzo(b)thiepine-1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use
CA002334773A Expired - Lifetime CA2334773C (en) 1998-06-10 1999-05-29 Benzothiepine-1,1-dioxide derivatives, method for producing them, medicaments containing these compounds and their use

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA002334773A Expired - Lifetime CA2334773C (en) 1998-06-10 1999-05-29 Benzothiepine-1,1-dioxide derivatives, method for producing them, medicaments containing these compounds and their use

Country Status (26)

Country Link
US (1) US6387944B1 (en)
EP (2) EP1086092B1 (en)
JP (2) JP4374426B2 (en)
KR (2) KR100681721B1 (en)
CN (2) CN1127497C (en)
AR (2) AR018633A1 (en)
AT (2) ATE227715T1 (en)
AU (2) AU753275B2 (en)
BR (2) BR9912188B1 (en)
CA (2) CA2334775C (en)
CZ (2) CZ297989B6 (en)
DE (3) DE19825804C2 (en)
DK (2) DK1086092T3 (en)
ES (2) ES2182535T3 (en)
HK (2) HK1039490A1 (en)
HU (2) HU229761B1 (en)
ID (2) ID28695A (en)
IL (1) IL140078A (en)
NO (1) NO327075B1 (en)
NZ (1) NZ508681A (en)
PL (2) PL196074B1 (en)
PT (2) PT1086092E (en)
RU (2) RU2215001C2 (en)
TR (2) TR200003634T2 (en)
WO (2) WO1999064410A1 (en)
ZA (2) ZA200007060B (en)

Families Citing this family (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6221897B1 (en) * 1998-06-10 2001-04-24 Aventis Pharma Deutschland Gmbh Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use
SE0000772D0 (en) 2000-03-08 2000-03-08 Astrazeneca Ab Chemical compounds
EG26979A (en) 2000-12-21 2015-03-01 Astrazeneca Ab Chemical compounds
IL156550A0 (en) * 2000-12-21 2004-01-04 Aventis Pharma Gmbh Novel 1,2-diphenzylazetidinones, method for producing the same, medicaments containing said compounds, and the use thereof for treating disorders of the lipid metabolism
IL160474A0 (en) * 2001-08-22 2004-07-25 Aventis Pharma Gmbh Combination products of 1,4-benzothiepine 1,1-dioxide derivatives with other active ingredients and the use thereof
GB0121337D0 (en) 2001-09-04 2001-10-24 Astrazeneca Ab Chemical compounds
GB0121622D0 (en) 2001-09-07 2001-10-31 Astrazeneca Ab Chemical compounds
GB0121621D0 (en) 2001-09-07 2001-10-31 Astrazeneca Ab Chemical compounds
NZ531796A (en) 2001-09-08 2005-10-28 Astrazeneca Ab Benzothiazepine and benzothiadiazepine derivatives with ileal bile acid transport (ibat) inhibitory activity for the treatment of hyperlipidaemia
GB0209467D0 (en) 2002-04-25 2002-06-05 Astrazeneca Ab Chemical compounds
GB0213669D0 (en) 2002-06-14 2002-07-24 Astrazeneca Ab Chemical compounds
SE0201937D0 (en) 2002-06-20 2002-06-20 Astrazeneca Ab Therapeutic agents
FR2848452B1 (en) * 2002-12-12 2007-04-06 Aventis Pharma Sa APPLICATION OF INTESTINAL BILIARY ACID RECAPTURE INHIBITORS FOR THE PREVENTION AND TREATMENT OF ALZHEIMER'S DISEASE
US20040138145A1 (en) * 2002-12-12 2004-07-15 Aventis Pharma S.A. Application of intestinal biliary acid reuptake inhibitors for the prevention and treatment of alzheimer's disease
GB0304194D0 (en) 2003-02-25 2003-03-26 Astrazeneca Ab Chemical compounds
GB0307918D0 (en) 2003-04-05 2003-05-14 Astrazeneca Ab Therapeutic use
DE102006053636B4 (en) * 2006-11-14 2008-09-18 Sanofi-Aventis Deutschland Gmbh New cyclohexyl substituted 1,4-benzothiepine 1,1-dioxide derivatives and their use
DE102006053635B4 (en) * 2006-11-14 2011-06-30 Sanofi-Aventis Deutschland GmbH, 65929 Novel benzyl-substituted 1,4-benzothiepine-1,1-dioxide derivatives, drugs containing these compounds and their use
US20100221513A1 (en) * 2008-09-05 2010-09-02 Wisconsin Alumni Research Foundation Self sintering transparent nanoporous thin-films for use in self-cleaning, anti-fogging, anti-corrosion, anti-erosion electronic and optical applications
ES2552657T3 (en) 2010-05-26 2015-12-01 Satiogen Pharmaceuticals, Inc. Inhibitors of the recycling of bile acids and satiogens for the treatment of diabetes, obesity, and inflammatory gastrointestinal conditions
HUE030062T2 (en) 2010-11-08 2017-04-28 Albireo Ab Ibat inhibitors for the treatment of liver diseases
MX345040B (en) 2010-11-08 2017-01-16 Albireo Ab A pharmaceutical combination comprising an ibat inhibitor and a bile acid binder.
CA2852957C (en) 2011-10-28 2020-08-04 Lumena Pharmaceuticals, Inc. Bile acid recycling inhibitors for treatment of hypercholemia and cholestatic liver disease
US20140243281A1 (en) * 2011-10-28 2014-08-28 Lumena Pharmaceuticals, Inc. Bile acid recycling inhibitors for treatment of pediatric cholestatic liver diseases
JP2016514684A (en) 2013-03-15 2016-05-23 ルメナ ファーマシューティカルズ エルエルシー Bile acid recirculation inhibitors for the treatment of primary sclerosing cholangitis and inflammatory bowel disease
BR112015023697A2 (en) 2013-03-15 2017-07-18 Lumena Pharmaceuticals Inc recycling bile acid inhibitors for treatment of barrett's esophagus and gastroesophageal reflux disease
JO3301B1 (en) 2013-04-26 2018-09-16 Albireo Ab Crystal modifications of elobixibat
US10709755B2 (en) 2014-06-25 2020-07-14 Elobix Ab Solid formulation and method for preventing or reducing coloration thereof
EP3012252A1 (en) 2014-10-24 2016-04-27 Ferring BV Crystal modifications of elobixibat
US10786529B2 (en) 2016-02-09 2020-09-29 Albireo Ab Oral cholestyramine formulation and use thereof
CA3011565C (en) 2016-02-09 2024-01-02 Albireo Ab Oral cholestyramine formulation and use thereof
US10441605B2 (en) 2016-02-09 2019-10-15 Albireo Ab Oral cholestyramine formulation and use thereof
US10441604B2 (en) 2016-02-09 2019-10-15 Albireo Ab Cholestyramine pellets and methods for preparation thereof
WO2017138878A1 (en) 2016-02-09 2017-08-17 Albireo Ab Oral cholestyramine formulation and use thereof
EP3664782A1 (en) 2017-08-09 2020-06-17 Albireo AB Cholestyramine pellets, oral cholestyramine formulations and use thereof
EP3664781A1 (en) 2017-08-09 2020-06-17 Albireo AB Cholestyramine granules, oral cholestyramine formulations and use thereof
ES2942443T3 (en) 2018-06-05 2023-06-01 Albireo Ab Benzothia(di)azepine compounds and their use as bile acid modulators
US10793534B2 (en) 2018-06-05 2020-10-06 Albireo Ab Benzothia(di)azepine compounds and their use as bile acid modulators
US11801226B2 (en) 2018-06-20 2023-10-31 Albireo Ab Pharmaceutical formulation of odevixibat
AU2019290337B2 (en) 2018-06-20 2023-01-12 Albireo Ab Crystal modifications of odevixibat
US11549878B2 (en) 2018-08-09 2023-01-10 Albireo Ab In vitro method for determining the adsorbing capacity of an insoluble adsorbant
US11007142B2 (en) 2018-08-09 2021-05-18 Albireo Ab Oral cholestyramine formulation and use thereof
US10722457B2 (en) 2018-08-09 2020-07-28 Albireo Ab Oral cholestyramine formulation and use thereof
US10941127B2 (en) 2019-02-06 2021-03-09 Albireo Ab Benzothiadiazepine compounds and their use as bile acid modulators
HUE060905T2 (en) 2019-02-06 2023-04-28 Albireo Ab Benzothiadiazepine compounds and their use as bile acid modulators
JP2022519664A (en) 2019-02-06 2022-03-24 アルビレオ・アクチボラグ Benzodiazepine compounds and their use as bile acid modulators
US10975045B2 (en) 2019-02-06 2021-04-13 Aibireo AB Benzothiazepine compounds and their use as bile acid modulators
EP4245367A3 (en) 2019-02-12 2023-12-20 Mirum Pharmaceuticals, Inc. Methods for treating cholestasis
US11014898B1 (en) 2020-12-04 2021-05-25 Albireo Ab Benzothiazepine compounds and their use as bile acid modulators
AR120683A1 (en) 2019-12-04 2022-03-09 Albireo Ab BENZOTHI(DI)AZEPINE COMPOUNDS AND THEIR USE AS BILIARY ACID
CA3158276A1 (en) 2019-12-04 2021-06-10 Per-Goran Gillberg Benzothia(di)azepine compounds and their use as bile acid modulators
CN114761018A (en) 2019-12-04 2022-07-15 阿尔比里奥公司 Benzothiadiazepine compounds and their use as bile acid modulators
AR120682A1 (en) 2019-12-04 2022-03-09 Albireo Ab BENZOTHIADIAZEPINE COMPOUNDS AND THEIR USE AS BILE ACID MODULATORS
TW202134218A (en) 2019-12-04 2021-09-16 瑞典商艾爾比瑞歐公司 Benzothiazepine compounds and their use as bile acid modulators
AR120676A1 (en) 2019-12-04 2022-03-09 Albireo Ab BENZOTHI(DI)AZEPINE COMPOUNDS AND THEIR USE AS BILIARY ACID
CR20220315A (en) 2019-12-04 2022-10-26 Albireo Ab BENZOTI(DI)AZEPINE COMPOUNDS AND THEIR USE AS BILE ACID MODULATORS
EP4069361B1 (en) 2019-12-04 2024-01-03 Albireo AB Benzothia(di)azepine compounds and their use as bile acid modulators
TW202134223A (en) 2019-12-04 2021-09-16 瑞典商艾爾比瑞歐公司 Benzothia(di)azepine compounds and their use as bile acid modulators
WO2022029101A1 (en) 2020-08-03 2022-02-10 Albireo Ab Benzothia(di)azepine compounds and their use as bile acid modulators
JP2023537285A (en) 2020-08-03 2023-08-31 アルビレオ・アクチボラグ Benzothia(di)azepine compounds and their use as bile acid modulators
CA3196488A1 (en) 2020-11-12 2022-05-19 Albireo Ab Odevixibat for treating progressive familial intrahepatic cholestasis (pfic)
KR20230117393A (en) 2020-12-04 2023-08-08 알비레오 에이비 Benzothia(di)azepine compounds and their use as bile acid regulators
TW202313579A (en) 2021-06-03 2023-04-01 瑞典商艾爾比瑞歐公司 Benzothia(di)azepine compounds and their use as bile acid modulators
WO2023237728A1 (en) 2022-06-09 2023-12-14 Albireo Ab Treating hepatitis
WO2024008766A1 (en) 2022-07-05 2024-01-11 Albireo Ab Benzothia(di)azepine compounds and their use as bile acid modulators

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5994391A (en) * 1994-09-13 1999-11-30 G.D. Searle And Company Benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
WO1996008484A1 (en) * 1994-09-13 1996-03-21 Monsanto Company Novel benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
CN1110494C (en) * 1996-03-11 2003-06-04 G·D·瑟尔公司 Novel benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
US6221897B1 (en) * 1998-06-10 2001-04-24 Aventis Pharma Deutschland Gmbh Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use
AU5301599A (en) * 1998-08-20 2000-03-14 Takeda Chemical Industries Ltd. Quaternary ammonium salts and their use

Also Published As

Publication number Publication date
DK1086092T3 (en) 2003-03-10
HU228570B1 (en) 2013-04-29
CZ20004592A3 (en) 2001-04-11
CN1127497C (en) 2003-11-12
ID26876A (en) 2001-02-15
RU2220141C2 (en) 2003-12-27
CA2334775C (en) 2009-10-13
PT1086092E (en) 2003-03-31
JP4374426B2 (en) 2009-12-02
HUP0102554A1 (en) 2001-10-28
PT1086113E (en) 2004-06-30
NO20006251D0 (en) 2000-12-08
AU4503199A (en) 1999-12-30
DE19825804A1 (en) 1999-12-16
AU4501999A (en) 1999-12-30
BR9911123B1 (en) 2010-12-14
JP2002517490A (en) 2002-06-18
ZA200007061B (en) 2001-07-18
RU2215001C2 (en) 2003-10-27
CZ297925B6 (en) 2007-05-02
KR100681721B1 (en) 2007-02-15
ES2182535T3 (en) 2003-03-01
JP3374129B2 (en) 2003-02-04
DE59908522D1 (en) 2004-03-18
IL140078A (en) 2004-08-31
TR200003632T2 (en) 2001-04-20
HUP0102256A1 (en) 2001-12-28
DK1086113T3 (en) 2004-05-24
WO1999064409A2 (en) 1999-12-16
WO1999064409A3 (en) 2000-03-02
JP2002517491A (en) 2002-06-18
NZ508681A (en) 2002-06-28
BR9912188B1 (en) 2010-12-14
AR018633A1 (en) 2001-11-28
CN1152039C (en) 2004-06-02
EP1086092B1 (en) 2002-11-13
AU752633B2 (en) 2002-09-26
NO327075B1 (en) 2009-04-20
KR100562184B1 (en) 2006-03-20
PL345901A1 (en) 2002-01-14
PL196057B1 (en) 2007-11-30
HUP0102554A3 (en) 2002-12-28
CA2334773C (en) 2009-05-26
BR9911123A (en) 2006-01-03
HK1036799A1 (en) 2002-01-18
CA2334773A1 (en) 1999-12-16
AU753275B2 (en) 2002-10-10
ZA200007060B (en) 2001-07-18
WO1999064410A1 (en) 1999-12-16
HUP0102256A3 (en) 2002-04-29
CZ20004591A3 (en) 2001-04-11
EP1086113B1 (en) 2004-02-11
TR200003634T2 (en) 2001-06-21
HU229761B1 (en) 2014-06-30
CZ297989B6 (en) 2007-05-16
DE19825804C2 (en) 2000-08-24
ATE227715T1 (en) 2002-11-15
PL344827A1 (en) 2001-11-19
BR9912188A (en) 2001-04-10
DE59903411D1 (en) 2002-12-19
ATE259372T1 (en) 2004-02-15
AR018634A1 (en) 2001-11-28
HK1039490A1 (en) 2002-04-26
ID28695A (en) 2001-06-28
CN1305487A (en) 2001-07-25
IL140078A0 (en) 2002-02-10
EP1086092A1 (en) 2001-03-28
KR20010052682A (en) 2001-06-25
EP1086113A2 (en) 2001-03-28
PL196074B1 (en) 2007-12-31
KR20010052701A (en) 2001-06-25
ES2215387T3 (en) 2004-10-01
US6387944B1 (en) 2002-05-14
NO20006251L (en) 2001-02-07
CN1305469A (en) 2001-07-25

Similar Documents

Publication Publication Date Title
CA2334775A1 (en) Benzo(b)thiepine-1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use
WO2000061568A3 (en) 1,4-benzothiazepine-1,1-dioxide derivatives substituted by sugar radicals, methods for the production thereof, medicaments containing these compounds and the use thereof
CA2445306A1 (en) Process for preparing 4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives
CA2475113A1 (en) Isothiazole derivatives useful as anticancer agents
CA2398620A1 (en) Pyrazine derivatives, pharmaceutical compositions containing them, and intermediates therefor
ES2018111A6 (en) 4H-1-benzopyran-4-one derivative or its salt, process for producing the same and pharmaceutical composition comprising the same as active ingredient
WO2003097656A3 (en) Novel substituted sulfamate anticonvulsant derivatives
CA2215013A1 (en) N-substituted indol-3-glyoxylamides having anti-asthmatic, antiallergic and immunosuppressant/immuno-modulating action
MEP9309A (en) Novel oligosaccharides, preparation method and pharmaceutical compositions containing the same
RU93049997A (en) DERIVATIVES OF METHYLENE-BIS-PHOSPHONIC ACID, METHOD FOR PRODUCING THEM, PHARMACEUTICAL COMPOSITION
YU94103A (en) Novel sulfonic acid derivatives
CA2219656A1 (en) Antibacterial cephalosporins
CA2265043A1 (en) Processes and intermediates for preparing substituted chromanol derivatives
CA2362217A1 (en) Process for preparing phenylpyrazole pesticidal intermediates
NO20004919D0 (en) Process for Preparation of 5-Hydroxybenzo [b] Thiophene-3-Carboxylic Acid Derivatives
AU7266291A (en) A novel substituted-amine compound and a process for the preparation thereof
WO2001010861A3 (en) Substituted heterocyclyl-2h-chromenes
BR9707004A (en) Compound process for preparing the same pharmaceutical composition using the compound and processes for treating diseases of the endokinological system and for the manufacture of a medicine
AU2002218422A1 (en) New desloratadine salts, process for their synthesis and pharmaceutical compositions thereof
NO20021727D0 (en) Process for Preparation of 3,4-Methylene Dioxymandelic Acid
CA2284501A1 (en) Antibacterial substituted 7-acylamino-3-(methylhydrazono) methyl-cephalosporins and intermediates
CA2149007A1 (en) Cyclohexane derivatives, process for their preparation, and the use of the compounds for the treatment of diseases
HUP0104213A2 (en) Vancoresmycin, a process for its production and its use as a pharmaceutical
CA2335394A1 (en) Aerothricin analogs, their preparation and use
ATE239017T1 (en) 1,4-DIHYDROPYRIDINE-5-CARBONIC ACID ESTER DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20160530