CN1040758C - 二氮杂双环壬烷的结晶形式的富马酸盐的制备方法 - Google Patents

二氮杂双环壬烷的结晶形式的富马酸盐的制备方法 Download PDF

Info

Publication number: CN1040758C
Authority: CN; China
Prior art keywords: compound; nonane; salt; fumarate; diazabicyclo
Prior art date: 1991-12-03
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.): Expired - Lifetime

Application number

CN92111096A

Other languages

English (en)

Chinese (zh)

Other versions

CN1072931A (zh

Inventor

U·雪恩

W·海特曼

U·麦茨尔

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.)

Abbott Products GmbH

Original Assignee

Solvay Pharmaceuticals BV

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.)

1991-12-03

Filing date

1992-09-26

Publication date

1998-11-18

1992-09-26 Application filed by Solvay Pharmaceuticals BV filed Critical Solvay Pharmaceuticals BV

1993-06-09 Publication of CN1072931A publication Critical patent/CN1072931A/zh

1998-11-18 Application granted granted Critical

1998-11-18 Publication of CN1040758C publication Critical patent/CN1040758C/zh

2007-09-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims description 36
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims description 26
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 title description 15
125000004122 cyclic group Chemical group 0.000 title 1
229910001873 dinitrogen Inorganic materials 0.000 title 1
239000003814 drug Substances 0.000 title 1
229940079593 drug Drugs 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
238000002425 crystallisation Methods 0.000 claims description 12
230000008025 crystallization Effects 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 11
239000001530 fumaric acid Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
239000002798 polar solvent Substances 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 3
239000003495 polar organic solvent Substances 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
235000002639 sodium chloride Nutrition 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000003513 alkali Substances 0.000 description 15
238000005984 hydrogenation reaction Methods 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 11
238000001035 drying Methods 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 10
238000012360 testing method Methods 0.000 description 10
238000004448 titration Methods 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
230000001476 alcoholic effect Effects 0.000 description 8
239000012452 mother liquor Substances 0.000 description 8
229940095064 tartrate Drugs 0.000 description 8
239000002253 acid Substances 0.000 description 7
CTIRHWCPXYGDGF-HDICACEKSA-N tedisamil Chemical compound [H][C@]12CN(CC3CC3)C[C@]([H])(CN(CC3CC3)C1)C21CCCC1 CTIRHWCPXYGDGF-HDICACEKSA-N 0.000 description 7
229960002926 tedisamil Drugs 0.000 description 7
230000004580 weight loss Effects 0.000 description 7
AOIVZQPSIHOHMP-HDICACEKSA-N (1r,5s)-7-(2-methylpropyl)-3-propan-2-ylspiro[3,7-diazabicyclo[3.3.1]nonane-9,1'-cyclohexane] Chemical compound C12([C@H]3CN(C[C@@H]2CN(C3)CC(C)C)C(C)C)CCCCC1 AOIVZQPSIHOHMP-HDICACEKSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
229950002035 bertosamil Drugs 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
229960001860 salicylate Drugs 0.000 description 5
206010013786 Dry skin Diseases 0.000 description 4
125000001118 alkylidene group Chemical group 0.000 description 4
239000013078 crystal Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
238000001291 vacuum drying Methods 0.000 description 4
NXXZICGFHYJPGE-UHFFFAOYSA-N 3,7-bis(cyclopropylmethyl)spiro[3,7-diazabicyclo[3.3.1]nonane-9,1'-cyclopentane];dihydrochloride Chemical compound Cl.Cl.C1C(C23CCCC3)CN(CC3CC3)CC2CN1CC1CC1 NXXZICGFHYJPGE-UHFFFAOYSA-N 0.000 description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
230000010247 heart contraction Effects 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
-1 nonane compound Chemical class 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
PPNCOQHHSGMKGI-UHFFFAOYSA-N 1-cyclononyldiazonane Chemical compound C1CCCCCCCC1N1NCCCCCCC1 PPNCOQHHSGMKGI-UHFFFAOYSA-N 0.000 description 1
208000004880 Polyuria Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
238000013019 agitation Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000003965 capillary gas chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
230000000857 drug effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000011194 food seasoning agent Nutrition 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
230000003993 interaction Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
238000000646 scanning calorimetry Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000005204 segregation Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000002411 thermogravimetry Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CN92111096A 1991-12-03 1992-09-26 二氮杂双环壬烷的结晶形式的富马酸盐的制备方法 Expired - Lifetime CN1040758C (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4139763A DE4139763A1 (de)	1991-12-03	1991-12-03	Kristalline fumarsaure salze von 9,9-alkylen-3,7-diazabicyclononan-verbindungen und diese verbindungen enthaltende arzneimittel
DEP4139763.0		1991-12-03

Publications (2)

Publication Number	Publication Date
CN1072931A CN1072931A (zh)	1993-06-09
CN1040758C true CN1040758C (zh)	1998-11-18

Family

ID=6446125

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN92111096A Expired - Lifetime CN1040758C (zh)	1991-12-03	1992-09-26	二氮杂双环壬烷的结晶形式的富马酸盐的制备方法

Country Status (24)

Country	Link
US (1)	US5324732A (2)
EP (1)	EP0550383B1 (2)
JP (1)	JP3180848B2 (2)
KR (1)	KR100252389B1 (2)
CN (1)	CN1040758C (2)
AT (1)	ATE124411T1 (2)
AU (1)	AU652869B2 (2)
CA (1)	CA2084489C (2)
CZ (1)	CZ281930B6 (2)
DE (2)	DE4139763A1 (2)
DK (1)	DK0550383T3 (2)
DZ (1)	DZ1636A1 (2)
ES (1)	ES2073900T3 (2)
FI (1)	FI100053B (2)
HU (3)	HU213672B (2)
IL (1)	IL103819A (2)
LT (1)	LTIP230A (2)
MX (1)	MX9206988A (2)
NO (1)	NO300687B1 (2)
NZ (1)	NZ245227A (2)
PH (1)	PH31114A (2)
SK (1)	SK332292A3 (2)
TW (1)	TW274084B (2)
ZA (1)	ZA928863B (2)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4421324A1 (de) *	1994-06-17	1995-12-21	Kali Chemie Pharma Gmbh	Neue 3,7-Diazabicyclo [3,3,1] nonan-Verbindungen enthaltende Arzneimittel
ES2284709T3 (es) *	2000-09-29	2007-11-16	Solvay Pharmaceuticals B.V.	Formulacion farmaceutica de liberacion sostenida independiente de la fuerza ionica.
TW200418468A (en) *	2002-11-18	2004-10-01	Solvay Pharm Gmbh	Liquid pharmaceutical formulations containing 3,7-diazabicyclo[3,3,1]nonane compounds and method of treatments relating to anti-arrhytmic events
AU2004260624A1 (en) *	2003-07-21	2005-02-10	Solvay Pharmaceuticals Gmbh	Use of 3,7-diazabicyclo`3, 3,1 !nonane compounds for the treatment and/or prophylaxis of anti-arrhythmic events in male human patients
US20050054667A1 (en) *	2003-07-21	2005-03-10	Solvay Pharmaceuticals Gmbh	Method of treating or inhibiting anti-arrhythmic events in male human patients
WO2005030207A1 (en) *	2003-09-26	2005-04-07	Solvay Pharmaceuticals Gmbh	Use of 3, 7-diazabicyclo (3.3.1) nonane compounds for the treatment of brugada syndrome

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2375235A1 (fr) *	1976-12-23	1978-07-21	Bayer Ag	Nouveaux diazabicyclo(3,3,1)nonanes, leur procede de preparation et medicament les contenant
EP0103833A2 (de) *	1982-09-18	1984-03-28	Kali-Chemie Pharma GmbH	Diazabicyclo-(3,3,1)-nonane
EP0306871A2 (de) *	1987-09-09	1989-03-15	Kali-Chemie Pharma GmbH	3,7-Diazabicyclo [3,3,1] nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2551283C3 (de) *	1975-11-14	1981-02-19	Hokuriku Pharmaceutical Co., Ltd., Katsuyama, Fukui (Japan)	Monofumarsäuresalz von 3-Pyridylmethylnikotinat und Verfahren zu seiner Herstellung
US4971992A (en) *	1989-03-27	1990-11-20	Hoechst-Roussel Pharmaceuticals Inc.	Carbonate derivatives of eseroline
DE4019080A1 (de) *	1990-06-15	1991-12-19	Kali Chemie Pharma Gmbh	Neue 3,7-diazabicycolo (3,3,1)nonan-verbindungen enthaltende arzneimittel

1991
- 1991-12-03 DE DE4139763A patent/DE4139763A1/de not_active Withdrawn
1992
- 1992-09-26 CN CN92111096A patent/CN1040758C/zh not_active Expired - Lifetime
- 1992-11-05 CZ CS923322A patent/CZ281930B6/cs not_active IP Right Cessation
- 1992-11-05 SK SK3322-92A patent/SK332292A3/sk not_active IP Right Cessation
- 1992-11-11 TW TW081109049A patent/TW274084B/zh not_active IP Right Cessation
- 1992-11-17 ZA ZA928863A patent/ZA928863B/xx unknown
- 1992-11-17 LT LTIP230A patent/LTIP230A/xx not_active Application Discontinuation
- 1992-11-19 PH PH45289A patent/PH31114A/en unknown
- 1992-11-20 IL IL10381992A patent/IL103819A/en not_active IP Right Cessation
- 1992-11-23 NZ NZ245227A patent/NZ245227A/en not_active IP Right Cessation
- 1992-11-23 US US07/980,177 patent/US5324732A/en not_active Expired - Lifetime
- 1992-11-24 DE DE59202726T patent/DE59202726D1/de not_active Expired - Lifetime
- 1992-11-24 EP EP92710032A patent/EP0550383B1/de not_active Expired - Lifetime
- 1992-11-24 DK DK92710032.1T patent/DK0550383T3/da active
- 1992-11-24 AT AT92710032T patent/ATE124411T1/de active
- 1992-11-24 ES ES92710032T patent/ES2073900T3/es not_active Expired - Lifetime
- 1992-11-25 HU HU9203698A patent/HU213672B/hu unknown
- 1992-11-25 KR KR1019920022371A patent/KR100252389B1/ko not_active Expired - Lifetime
- 1992-11-25 HU HU9203698A patent/HU9203698D0/hu unknown
- 1992-11-25 DZ DZ920147A patent/DZ1636A1/fr active
- 1992-12-02 FI FI925482A patent/FI100053B/fi not_active IP Right Cessation
- 1992-12-02 NO NO19924647A patent/NO300687B1/no not_active IP Right Cessation
- 1992-12-02 JP JP32309192A patent/JP3180848B2/ja not_active Expired - Lifetime
- 1992-12-02 AU AU29815/92A patent/AU652869B2/en not_active Expired
- 1992-12-03 CA CA002084489A patent/CA2084489C/en not_active Expired - Lifetime
- 1992-12-03 MX MX9206988A patent/MX9206988A/es unknown
1994
- 1994-09-30 HU HU94P/P00033P patent/HU210215A9/hu unknown

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2375235A1 (fr) *	1976-12-23	1978-07-21	Bayer Ag	Nouveaux diazabicyclo(3,3,1)nonanes, leur procede de preparation et medicament les contenant
EP0103833A2 (de) *	1982-09-18	1984-03-28	Kali-Chemie Pharma GmbH	Diazabicyclo-(3,3,1)-nonane
EP0306871A2 (de) *	1987-09-09	1989-03-15	Kali-Chemie Pharma GmbH	3,7-Diazabicyclo [3,3,1] nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel

Also Published As

Publication number	Publication date
JPH05247040A (ja)	1993-09-24
DE4139763A1 (de)	1993-06-09
HK1006568A1 (en)	1999-03-05
FI925482A0 (fi)	1992-12-02
KR100252389B1 (ko)	2000-05-01
US5324732A (en)	1994-06-28
PH31114A (en)	1998-02-23
FI925482L (fi)	1993-06-04
NZ245227A (en)	1994-06-27
CZ332292A3 (en)	1993-08-11
NO924647D0 (no)	1992-12-02
CA2084489C (en)	2002-10-08
ZA928863B (en)	1993-05-13
HU210215A9 (en)	1995-02-28
HU9203698D0 (en)	1993-03-29
IL103819A (en)	1996-09-12
SK279519B6 (sk)	1998-12-02
SK332292A3 (en)	1998-12-02
MX9206988A (es)	1993-06-01
LTIP230A (en)	1994-05-15
AU652869B2 (en)	1994-09-08
CA2084489A1 (en)	1993-06-04
DE59202726D1 (de)	1995-08-03
ES2073900T3 (es)	1995-08-16
CZ281930B6 (cs)	1997-04-16
ATE124411T1 (de)	1995-07-15
CN1072931A (zh)	1993-06-09
HUT63417A (en)	1993-08-30
HU213672B (en)	1997-09-29
KR930012772A (ko)	1993-07-21
IL103819A0 (en)	1993-04-04
EP0550383A1 (de)	1993-07-07
AU2981592A (en)	1993-06-10
NO924647L (no)	1993-06-04
EP0550383B1 (de)	1995-06-28
FI100053B (fi)	1997-09-15
JP3180848B2 (ja)	2001-06-25
DK0550383T3 (da)	1995-08-28
NO300687B1 (no)	1997-07-07
DZ1636A1 (fr)	2002-02-17
TW274084B (2)	1996-04-11

Legal Events

Date	Code	Title	Description
1993-06-09	C06	Publication
1993-06-09	PB01	Publication
1995-02-01	C10	Entry into substantive examination
1995-02-01	SE01	Entry into force of request for substantive examination
1998-11-18	C14	Grant of patent or utility model
1998-11-18	GR01	Patent grant
2002-06-12	C15	Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993)
2002-06-12	OR01	Other related matters
2012-07-11	C56	Change in the name or address of the patentee	Owner name: ABBOTT PRODUCTS, INC. Free format text: FORMER NAME: SOLVAY PHARMACEUTICALS GMBH
2012-07-11	CP01	Change in the name or title of a patent holder	Address after: Hannover, Federal Republic of Germany Patentee after: Solvay Pharm GmbH Address before: Hannover, Federal Republic of Germany Patentee before: Solvay Pharmaceuticals GmbH
2012-11-14	C17	Cessation of patent right
2012-11-14	CX01	Expiry of patent term	Expiration termination date: 20120926 Granted publication date: 19981118

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