CS259891B2 - Method of crystalline thorasemide preparation in pure modification i - Google Patents

Method of crystalline thorasemide preparation in pure modification i Download PDF

Info

Publication number: CS259891B2
Authority: CS; Czechoslovakia
Prior art keywords: modification; torasemide; preparation; pure; water
Prior art date: 1985-08-17

Application number

CS865945A

Other languages

Czech (cs)

English (en)

Other versions

CS594586A2 (en

Inventor

Fritz Topfmeier

Gustav Lettenbauer

Original Assignee

Boehringer Mannheim 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.)

1985-08-17

Filing date

1986-08-11

Publication date

1988-11-15

1986-08-11 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1988-03-15 Publication of CS594586A2 publication Critical patent/CS594586A2/cs

1988-11-15 Publication of CS259891B2 publication Critical patent/CS259891B2/cs

Links

230000004048 modification Effects 0.000 title claims description 60
238000012986 modification Methods 0.000 title claims description 60
238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title description 8
NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 claims description 47
229960005461 torasemide Drugs 0.000 claims description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
239000000243 solution Substances 0.000 claims description 10
238000002844 melting Methods 0.000 claims description 8
230000008018 melting Effects 0.000 claims description 8
239000000725 suspension Substances 0.000 claims description 7
238000001556 precipitation Methods 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 3
239000012670 alkaline solution Substances 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
230000008707 rearrangement Effects 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
238000004090 dissolution Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000008187 granular material Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000000047 product Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
230000008859 change Effects 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
229940099112 cornstarch Drugs 0.000 description 3
239000008101 lactose Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
239000000356 contaminant Substances 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000001882 diuretic effect Effects 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
238000002424 x-ray crystallography Methods 0.000 description 2
-1 4-m-toluidino-3-pyridyl Chemical group 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
208000004880 Polyuria Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical compound [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
238000010998 test method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Hematology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)
Compounds Of Unknown Constitution (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Enzymes And Modification Thereof (AREA)

CS865945A 1985-08-17 1986-08-11 Method of crystalline thorasemide preparation in pure modification i CS259891B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853529529 DE3529529A1 (de)	1985-08-17	1985-08-17	Verfahren zur herstellung einer stabilen modifikation von torasemid

Publications (2)

Publication Number	Publication Date
CS594586A2 CS594586A2 (en)	1988-03-15
CS259891B2 true CS259891B2 (en)	1988-11-15

Family

ID=6278766

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CS865945A CS259891B2 (en)	1985-08-17	1986-08-11	Method of crystalline thorasemide preparation in pure modification i
CS914199A CS419991A3 (en)	1985-08-17	1991-12-31	Pharmaceutical preparations

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CS914199A CS419991A3 (en)	1985-08-17	1991-12-31	Pharmaceutical preparations

Country Status (25)

Country	Link
US (4)	US4743693A (fr)
EP (1)	EP0212537B1 (fr)
JP (2)	JPS6245576A (fr)
KR (1)	KR930009818B1 (fr)
AU (1)	AU573454B2 (fr)
CA (1)	CA1307277C (fr)
CS (2)	CS259891B2 (fr)
DD (1)	DD259858A5 (fr)
DE (2)	DE3529529A1 (fr)
DK (1)	DK162518C (fr)
ES (1)	ES2001522A6 (fr)
FI (1)	FI82189C (fr)
GR (1)	GR862139B (fr)
HK (1)	HK59994A (fr)
HU (1)	HU195778B (fr)
IE (1)	IE59237B1 (fr)
IL (1)	IL79672A (fr)
LT (1)	LT3596B (fr)
NO (1)	NO170079C (fr)
NZ (1)	NZ217172A (fr)
PL (1)	PL146086B1 (fr)
PT (1)	PT83186B (fr)
SU (1)	SU1480766A3 (fr)
UA (1)	UA7080A1 (fr)
ZA (1)	ZA866151B (fr)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3623620A1 (de) *	1986-07-12	1988-01-21	Boehringer Mannheim Gmbh	Spritzfertige, waessrige, alkalische injektionsloesungen von torasemid und verfahren zu ihrer herstellung
US5166162A (en) *	1990-03-02	1992-11-24	Adir Et Compagnie	Pyridylsulfonylurea and pyridylsulfonylthiourea compounds
JP3586471B2 (ja) *	1991-06-25	2004-11-10	三菱ウェルファーマ株式会社	トラセミド含有医薬組成物
TW257757B (fr) *	1993-03-03	1995-09-21	Boehringer Mannheim Gmbh
HRP980532B1 (en) *	1998-10-02	2005-06-30	Pliva	Novel crystalline torasemide modification
US6166045A (en)	1998-06-02	2000-12-26	Roche Diagnostics Gmbh	Torasemide of modification III
US5914336A (en)	1998-06-02	1999-06-22	Boehringer Mannheim Gmbh	Method of controlling the serum solubility of orally administered torasemide and composition relating thereto
US20030026835A1 (en) *	1999-02-15	2003-02-06	Sumitomo Pharmaceuticals Company Limited	Tablets disintegrating rapidly in the oral cavity
JP2003527319A (ja) *	1999-08-11	2003-09-16	テバファーマシューティカルインダストリーズリミティド	トルセミド多形体
DK1292303T3 (da)	2000-02-17	2004-09-06	Teva Pharma	Stabil farmaceutisk formulering omfattende torsemidmodifikation II
HUP0300241A3 (en)	2000-03-20	2005-11-28	Teva Pharma	Processes for preparing torsemide intermediate
HRP20000162B1 (en) *	2000-03-20	2004-06-30	Pliva D D	Amorphous torasemide modification
HRP20000765A2 (en) *	2000-11-10	2002-06-30	Pliva D D	Compositions of n-(1-methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridylsulfonamide and cyclic oligosaccharides with increased release
US20030022921A1 (en) *	2001-02-21	2003-01-30	Minutza Leibovici	Stable pharmaceutical formulation comprising torsemide modification II
IN192178B (fr) *	2001-08-03	2004-03-06	Ranbaxy Lab
EP2316468A1 (fr)	2002-02-22	2011-05-04	Shire LLC	Système de distribution et méthodes de protection et d'administration de dextroamphetamine
ITMI20020639A1 (it) *	2002-03-27	2003-09-29	Cosma S P A	Composizioni farmaceutiche comprendenti come principio attivo 1-isopropil-3°(4-m-toluidino-3-pridil)sulfonil!-urea
HRP20020603B1 (en) *	2002-07-19	2008-11-30	Pliva D.D.	New process for the preparation of modification i n-(1-methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridinesulfonamide
EP1465890B1 (fr) *	2002-11-18	2007-04-04	Teva Pharmaceutical Industries Ltd.	Lansoprazole stable contenant plus de 500 parties par million, jusqu'a environ 3000 parties par million d'eau et plus de 200 parties par million, jusqu'a environ 5000 parties par million d'alcool
EP1485373A1 (fr) *	2003-02-05	2004-12-15	Teva Pharmaceutical Industries Limited	Procede de stabilisation de lansoprazole
ES2244324B1 (es) *	2004-03-25	2006-11-16	Ferrer Internacional, S.A.	Composiciones diureticas de liberacion prolongada.
AT500576B1 (de) *	2004-07-28	2006-11-15	Sanochemia Pharmazeutika Ag	Verfahren zur reindarstellung von kristallformen von torsemid
US10178893B1 (en) *	2013-06-14	2019-01-15	Scott Bradley Baker	Shoe
FR3018688A1 (fr) *	2014-03-19	2015-09-25	Virbac	Utilisation de torasemide a faible dose dans une composition veterinaire
EP3031471A1 (fr)	2014-12-12	2016-06-15	Ceva Sante Animale	Composition vétérinaire pour le traitement de l'oedème pulmonaire associé à l'insuffisance cardiaque chez les animaux domestiques
US12048677B2 (en)	2014-12-12	2024-07-30	Ceva Sante Animale	Compositions and uses thereof for the treatment of heart failure in domestic animals
DK3173075T3 (en) *	2015-11-27	2019-01-21	Accupharma Spolka Z Ograniczona Odpowiedzialnoscia	PHARMACEUTICAL COMBINATION PREPARATION OF ACE INHIBITOR AND LOOPDIURETIC
CN115417810B (zh) *	2022-09-22	2023-10-10	南京正科医药股份有限公司	一种托拉塞米晶型ⅰ的精制方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US30633A (en) *		1860-11-13		Improvement in fire-escapes
GB1477664A (en) *	1974-04-17	1977-06-22	Christiaens Sa A	Pyridine derivatives
GB1593609A (en) *	1978-01-31	1981-07-22	Christiaens Sa A	Pyridine sulfonamides
LU85193A1 (fr) *	1984-01-31	1985-09-12	Christiaens Sa A	Nouveaux derives de la 4-phenylaminopyridine,leur utilisation et leur preparation

1985
- 1985-08-17 DE DE19853529529 patent/DE3529529A1/de active Granted
1986
- 1986-08-10 IL IL79672A patent/IL79672A/xx not_active IP Right Cessation
- 1986-08-11 US US06/895,355 patent/US4743693A/en not_active Ceased
- 1986-08-11 AU AU61055/86A patent/AU573454B2/en not_active Expired
- 1986-08-11 CA CA000515676A patent/CA1307277C/fr not_active Expired - Lifetime
- 1986-08-11 CS CS865945A patent/CS259891B2/cs not_active IP Right Cessation
- 1986-08-12 PT PT83186A patent/PT83186B/pt unknown
- 1986-08-12 NZ NZ217172A patent/NZ217172A/xx unknown
- 1986-08-12 DE DE8686111118T patent/DE3667970D1/de not_active Expired - Lifetime
- 1986-08-12 EP EP86111118A patent/EP0212537B1/fr not_active Expired - Lifetime
- 1986-08-13 IE IE217986A patent/IE59237B1/en not_active IP Right Cessation
- 1986-08-13 DK DK385586A patent/DK162518C/da not_active IP Right Cessation
- 1986-08-14 KR KR1019860006689A patent/KR930009818B1/ko not_active Expired - Lifetime
- 1986-08-14 GR GR862139A patent/GR862139B/el unknown
- 1986-08-14 DD DD86293655A patent/DD259858A5/de not_active IP Right Cessation
- 1986-08-14 ES ES8601131A patent/ES2001522A6/es not_active Expired
- 1986-08-15 SU SU864027953A patent/SU1480766A3/ru active
- 1986-08-15 NO NO863305A patent/NO170079C/no not_active IP Right Cessation
- 1986-08-15 ZA ZA866151A patent/ZA866151B/xx unknown
- 1986-08-15 HU HU863598A patent/HU195778B/hu unknown
- 1986-08-15 FI FI863305A patent/FI82189C/fi not_active IP Right Cessation
- 1986-08-15 PL PL1986261052A patent/PL146086B1/pl unknown
- 1986-08-15 UA UA4027953A patent/UA7080A1/uk unknown
- 1986-08-18 JP JP61191789A patent/JPS6245576A/ja active Granted
1987
- 1987-10-20 US US07/111,439 patent/US4822807A/en not_active Ceased
1989
- 1989-10-27 JP JP1278800A patent/JPH0643400B2/ja not_active Expired - Lifetime
1991
- 1991-12-31 CS CS914199A patent/CS419991A3/cs unknown
1992
- 1992-12-03 US US07/985,053 patent/USRE34580E/en not_active Expired - Lifetime
1993
- 1993-04-08 US US08/043,631 patent/USRE34672E/en not_active Expired - Lifetime
- 1993-08-27 LT LTIP898A patent/LT3596B/lt not_active IP Right Cessation
1994
- 1994-06-23 HK HK59994A patent/HK59994A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE3667970D1 (de)	1990-02-08
FI863305A0 (fi)	1986-08-15
DK385586D0 (da)	1986-08-13
JPH02191255A (ja)	1990-07-27
DK162518C (da)	1992-03-30
DK385586A (da)	1987-02-18
USRE34672E (en)	1994-07-26
NO170079C (no)	1992-09-09
CA1307277C (fr)	1992-09-08
AU573454B2 (en)	1988-06-09
NO170079B (no)	1992-06-01
ZA866151B (en)	1987-04-29
NO863305L (no)	1987-02-18
UA7080A1 (uk)	1995-06-30
PT83186A (de)	1986-09-01
EP0212537B1 (fr)	1990-01-03
IL79672A (en)	1990-01-18
JPH0415205B2 (fr)	1992-03-17
ES2001522A6 (es)	1988-06-01
HUT42069A (en)	1987-06-29
FI82189B (fi)	1990-10-31
CS594586A2 (en)	1988-03-15
US4743693A (en)	1988-05-10
USRE34580E (en)	1994-04-05
NZ217172A (en)	1989-02-24
JPS6245576A (ja)	1987-02-27
DK162518B (da)	1991-11-11
LT3596B (en)	1995-12-27
KR870002076A (ko)	1987-03-30
US4822807A (en)	1989-04-18
CS419991A3 (en)	1992-06-17
FI863305L (fi)	1987-02-18
DD259858A5 (de)	1988-09-07
IL79672A0 (en)	1986-11-30
FI82189C (fi)	1991-02-11
PL261052A1 (en)	1987-11-02
HU195778B (en)	1988-07-28
HK59994A (en)	1994-07-08
EP0212537A1 (fr)	1987-03-04
KR930009818B1 (ko)	1993-10-11
GR862139B (en)	1986-12-30
JPH0643400B2 (ja)	1994-06-08
LTIP898A (en)	1995-03-27
NO863305D0 (no)	1986-08-15
PL146086B1 (en)	1988-12-31
IE862179L (en)	1987-02-17
AU6105586A (en)	1987-02-19
IE59237B1 (en)	1994-01-26
PT83186B (pt)	1988-07-01
DE3529529C2 (fr)	1987-05-27
DE3529529A1 (de)	1987-02-19
SU1480766A3 (ru)	1989-05-15

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2001-10-17	MK4A	Patent expired	Effective date: 20010811

Publication	Publication Date	Title
CS259891B2 (en)	1988-11-15	Method of crystalline thorasemide preparation in pure modification i
CA2424462C (fr)	2010-03-30	Compositions pharmaceutiques d'acide clavulanique
GB2114969A (en)	1983-09-01	Penicillins
RU2125571C1 (ru)	1999-01-27	СОЛЬ 7-([1α,5α,6α]-6-АМИНО-3-АЗАБИЦИКЛО [3.1.0] ГЕКС-3-ИЛ)-6-ФТОР-1-(2,4-ДИФТОРФЕНИЛ)-1,4- ДИГИДРО-4-ОКСО-1,8-НАФТИРИДИН-3-КАРБОНОВОЙ И МЕТАНСУЛЬФОНОВОЙ КИСЛОТ И СПОСОБ ЕЕ ПОЛУЧЕНИЯ
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