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

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) AR018634A1 (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) ZA200007061B (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
WO2002050027A1 (en) * 2000-12-21 2002-06-27 Aventis Pharma Deutschland 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
JP2005501861A (en) * 2001-08-22 2005-01-20 アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング Combinations of 1,4-benzothiepine 1,1-dioxide derivatives with other active substances and their use
GB0121337D0 (en) 2001-09-04 2001-10-24 Astrazeneca Ab Chemical compounds
GB0121621D0 (en) 2001-09-07 2001-10-31 Astrazeneca Ab Chemical compounds
GB0121622D0 (en) 2001-09-07 2001-10-31 Astrazeneca Ab Chemical compounds
DE60217136T2 (en) 2001-09-08 2007-09-27 Astrazeneca Ab BENZOTHIAZEPINE AND BENZOTHIADIAZEPINE DERIVATIVE WITH HEMMETIC EFFECT ON THE ACID TRANSPORT IN THE GALLENGES 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
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
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
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
EP2575821B1 (en) 2010-05-26 2015-08-12 Satiogen Pharmaceuticals, Inc. Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions
ES2687027T3 (en) 2010-11-08 2018-10-23 Albireo Ab Ibat inhibitors for the treatment of liver diseases
CN103228270B (en) 2010-11-08 2016-02-10 阿尔比里奥公司 Containing the drug regimen of ibat inhibitor and bile acid binding agent
MX363161B (en) 2011-10-28 2019-03-13 Lumena Pharmaceuticals Inc Bile acid recycling inhibitors for treatment of hypercholemia and cholestatic liver disease.
ES2633766T3 (en) 2011-10-28 2017-09-25 Lumena Pharmaceuticals Llc Bile acid recycling inhibitors for the treatment of pediatric cholestatic liver diseases
KR20160002773A (en) 2013-03-15 2016-01-08 루메나 파마수티컬즈, 인코포레이티드 Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease
MX2015013196A (en) 2013-03-15 2016-04-15 Lumena Pharmaceuticals Inc Bile acid recycling 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
CA2952406A1 (en) 2014-06-25 2015-12-30 Ea Pharma Co., Ltd. Solid formulation and method for preventing or reducing coloration thereof
EP3012252A1 (en) 2014-10-24 2016-04-27 Ferring BV Crystal modifications of elobixibat
ES2874546T3 (en) 2016-02-09 2021-11-05 Albireo Ab Oral formulation of cholestyramine and its use
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
US10786529B2 (en) 2016-02-09 2020-09-29 Albireo Ab Oral cholestyramine formulation and use thereof
JP6954926B2 (en) 2016-02-09 2021-10-27 アルビレオ・アクチボラグ Oral cholestyramine preparation and its use
CA3071182A1 (en) 2017-08-09 2019-02-14 Albireo Ab Cholestyramine pellets, oral cholestyramine formulations and use thereof
WO2019032026A1 (en) 2017-08-09 2019-02-14 Albireo Ab Cholestyramine granules, oral cholestyramine formulations and use thereof
US10793534B2 (en) 2018-06-05 2020-10-06 Albireo Ab Benzothia(di)azepine compounds and their use as bile acid modulators
JP7391048B2 (en) 2018-06-05 2023-12-04 アルビレオ・アクチボラグ 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
CA3100687A1 (en) 2018-06-20 2019-12-26 Albireo Ab Pharmaceutical formulation 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
PL3921028T3 (en) 2019-02-06 2023-02-13 Albireo Ab Benzothiadiazepine compounds and their use as bile acid modulators
US10941127B2 (en) 2019-02-06 2021-03-09 Albireo Ab Benzothiadiazepine compounds and their use as bile acid modulators
CA3127408A1 (en) 2019-02-06 2020-08-13 Albireo Ab Benzothiazepine 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
CA3129827A1 (en) 2019-02-12 2020-08-20 Mirum Pharmaceuticals, Inc. Genotype and dose-dependent response to an asbti in patients with bile salt export pump deficiency
AR120682A1 (en) 2019-12-04 2022-03-09 Albireo Ab BENZOTHIADIAZEPINE 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
EP4069359B1 (en) 2019-12-04 2024-01-03 Albireo AB Benzothia(di)azepine compounds and their use as bile acid modulators
WO2021110883A1 (en) 2019-12-04 2021-06-10 Albireo Ab Benzothia(di)azepine compounds and their use as bile acid modulators
DK4069360T3 (en) 2019-12-04 2024-02-26 Albireo Ab BENZOTHIA(DI)AZEPINE COMPOUNDS AND THEIR USE AS BILE ACID MODULATORS
WO2021110884A1 (en) 2019-12-04 2021-06-10 Albireo Ab Benzothia(di)azepine compounds and their use as bile acid modulators
WO2021110886A1 (en) 2019-12-04 2021-06-10 Albireo Ab Benzothia(di)azepine compounds and their use as bile acid modulators
US11014898B1 (en) 2020-12-04 2021-05-25 Albireo Ab Benzothiazepine compounds and their use as bile acid modulators
EP4069247A1 (en) 2019-12-04 2022-10-12 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
EP4188541A1 (en) 2020-08-03 2023-06-07 Albireo AB 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
JP2023549226A (en) 2020-11-12 2023-11-22 アルビレオ エービー Odevixibat for the treatment of progressive familial intrahepatic cholestasis (PFIC)
AU2021390172A1 (en) 2020-12-04 2023-06-22 Albireo Ab Benzothia(di)azepine compounds and their use as bile acid modulators
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
US20230398125A1 (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
DK0781278T3 (en) * 1994-09-13 2001-04-17 Monsanto Co New benzothiepines which have activity as inhibitors of ileal bile acid transport and taurocholate uptake
EP0888333B1 (en) * 1996-03-11 2005-08-31 G.D. Searle LLC 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
CA2337307A1 (en) * 1998-08-20 2000-03-02 Osamu Nishimura Quaternary ammonium salts and their use

Also Published As

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

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
WO2000061568A8 (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
HUT59400A (en) Process for producing thiazole acylamino derivatives substituted with heterocyclic group, as well as pharmaceutical compositions comprising such compounds as active ingredient
CA2475113A1 (en) Isothiazole derivatives useful as anticancer agents
CA2398620A1 (en) Pyrazine derivatives, pharmaceutical compositions containing them, and intermediates therefor
ES2017836A6 (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
CA2378382A1 (en) Carboxylic acid amides, pharmaceutical compositions containing these compounds, the use and preparation thereof
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
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
CA2335394A1 (en) Aerothricin analogs, their preparation and use
WO2000058282A3 (en) Novel [(2-substituted-5 -[3-thienyl) -benzyl]-[2- ([2-isopropoxy-5-fluoro] -phenoxy) -ethyl] -amine derivatives, method for the production and use thereof as medicaments

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20160530