CZ281930B6 - Krystalické soli kyseliny fumarové s 9,9-alkylen 3,7-diazabicyklononanovými sloučeninami a léčiva obsahující tyto sloučeniny - Google Patents

Krystalické soli kyseliny fumarové s 9,9-alkylen 3,7-diazabicyklononanovými sloučeninami a léčiva obsahující tyto sloučeniny Download PDF

Info

Publication number: CZ281930B6
Authority: CZ; Czechia
Prior art keywords: fumaric acid; diazabicyclo; nonane; compounds; alkylene
Prior art date: 1991-12-03

Application number

CS923322A

Other languages

Czech (cs)

English (en)

Inventor

Uwe Dr. Schön

Walter Dr. Heitmann

Uwe Dr. Mätzel

Original Assignee

Solvay Pharmaceuticals 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.)

1991-12-03

Filing date

1992-11-05

Publication date

1997-04-16

1992-11-05 Application filed by Solvay Pharmaceuticals Gmbh filed Critical Solvay Pharmaceuticals Gmbh

1993-08-11 Publication of CZ332292A3 publication Critical patent/CZ332292A3/cs

1997-04-16 Publication of CZ281930B6 publication Critical patent/CZ281930B6/cs

Links

VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims abstract description 47
150000003839 salts Chemical class 0.000 title claims abstract description 25
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims abstract description 18
239000001530 fumaric acid Substances 0.000 title claims abstract description 16
150000001875 compounds Chemical class 0.000 title claims description 16
238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 6
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical class CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 title description 4
239000000825 pharmaceutical preparation Substances 0.000 title description 2
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000002798 polar solvent Substances 0.000 claims description 7
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
239000003495 polar organic solvent Substances 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
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 14
229950002035 bertosamil Drugs 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
239000002253 acid Substances 0.000 description 10
238000001035 drying Methods 0.000 description 10
CTIRHWCPXYGDGF-HDICACEKSA-N tedisamil Chemical group [H][C@]12CN(CC3CC3)C[C@]([H])(CN(CC3CC3)C1)C21CCCC1 CTIRHWCPXYGDGF-HDICACEKSA-N 0.000 description 10
229960002926 tedisamil Drugs 0.000 description 10
230000004580 weight loss Effects 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 9
238000004448 titration Methods 0.000 description 9
230000001476 alcoholic effect Effects 0.000 description 8
239000012452 mother liquor Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000000113 differential scanning calorimetry Methods 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000000052 comparative effect Effects 0.000 description 4
229960001860 salicylate Drugs 0.000 description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
-1 compounds 9,9, N, N'-tetrasubstituted 3,7-diazabicyclo [3.3.1] nonane Chemical class 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
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 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
239000001358 L(+)-tartaric acid Substances 0.000 description 2
235000011002 L(+)-tartaric acid Nutrition 0.000 description 2
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000013557 residual solvent Substances 0.000 description 2
229960004889 salicylic acid Drugs 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical compound C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 1
208000004880 Polyuria Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-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
230000000747 cardiac effect Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001382 dynamic differential scanning calorimetry Methods 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000000892 gravimetry Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000000297 inotrophic effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
230000001550 time effect Effects 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 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)

CS923322A 1991-12-03 1992-11-05 Krystalické soli kyseliny fumarové s 9,9-alkylen 3,7-diazabicyklononanovými sloučeninami a léčiva obsahující tyto sloučeniny CZ281930B6 (cs)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
CZ332292A3 CZ332292A3 (en)	1993-08-11
CZ281930B6 true CZ281930B6 (cs)	1997-04-16

Family

ID=6446125

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS923322A CZ281930B6 (cs)	1991-12-03	1992-11-05	Krystalické soli kyseliny fumarové s 9,9-alkylen 3,7-diazabicyklononanovými sloučeninami a léčiva obsahující tyto sloučeniny

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

Family Cites Families (6)

* 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
DE2658558A1 (de) *	1976-12-23	1978-06-29	Bayer Ag	Diazabicyclo(3,3,1)nonane, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3234697A1 (de) *	1982-09-18	1984-03-22	Kali-Chemie Pharma Gmbh, 3000 Hannover	Neue diazabicyclo-(3,3,1)-nonane
PT88381B (pt) *	1987-09-09	1995-07-06	Kali Chemie Pharma Gmbh	Processo para a preparacao de novos compostos 3,7-diazabiciclo{3,3,1} nonano, e de composicoes farmaceuticas que contem estes compostos
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

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
CN1040758C (zh)	1998-11-18
CA2084489A1 (en)	1993-06-04
DE59202726D1 (de)	1995-08-03
ES2073900T3 (es)	1995-08-16
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
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2012-11-14	MK4A	Patent expired	Effective date: 20121105

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US4794185A (en)	1988-12-27	Process for the preparation of imidazopyridines
RU2644160C2 (ru)	2018-02-08	Химический способ
US3705907A (en)	1972-12-12	4-(2-hydroxy)-3-aminopropoxy)-indole derivatives
DK161966B (da)	1991-09-02	Fremgangsmaade til fremstilling af 5-aroylerede 1,2-dihydro-3h-pyrrolooe1,2-aaapyrrol-1-carboxylsyrer eller estere eller farmaceutisk acceptable salte deraf
US3652569A (en)	1972-03-28	Ergonine ergoptine and the 1-methyl and 9 10-dihydro derivatives thereof
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