SK542004A3 - Polymorph salt of a pyridazinone derivative for the treatment arrhythmia - Google Patents

Polymorph salt of a pyridazinone derivative for the treatment arrhythmia Download PDF

Info

Publication number: SK542004A3
Authority: SK; Slovakia
Prior art keywords: ethyl; chloro; pyridazinone; dimethoxyphenyl; fumarate
Prior art date: 2001-07-26

Application number

SK54-2004A

Other languages

English (en)

Slovak (sk)

Inventor

Nagy Peter Kotay

Gyula Simig

Jozsef Barkoczy

Kirallyi Zsuzsa Szent

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

2001-07-26

Filing date

2002-07-26

Publication date

2004-08-03

2002-07-26 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

2004-08-03 Publication of SK542004A3 publication Critical patent/SK542004A3/sk

Links

206010003119 arrhythmia Diseases 0.000 title claims abstract description 9
230000006793 arrhythmia Effects 0.000 title claims abstract description 9
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 7
150000003839 salts Chemical class 0.000 title description 8
238000000034 method Methods 0.000 claims abstract description 23
238000002360 preparation method Methods 0.000 claims abstract description 23
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
GFNWSKLPHRHAOE-WLHGVMLRSA-N (e)-but-2-enedioic acid;4-chloro-5-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propylamino]-1h-pyridazin-6-one Chemical compound OC(=O)\C=C\C(O)=O.C1=C(OC)C(OC)=CC=C1CCN(C)CCCNC1=C(Cl)C=NNC1=O GFNWSKLPHRHAOE-WLHGVMLRSA-N 0.000 claims abstract description 10
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 63
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 52
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
125000006308 propyl amino group Chemical group 0.000 claims description 19
239000000243 solution Substances 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
239000004480 active ingredient Substances 0.000 claims description 13
238000010438 heat treatment Methods 0.000 claims description 13
239000001530 fumaric acid Substances 0.000 claims description 12
239000012442 inert solvent Substances 0.000 claims description 11
239000007788 liquid Substances 0.000 claims description 9
239000000725 suspension Substances 0.000 claims description 9
238000001816 cooling Methods 0.000 claims description 8
239000000843 powder Substances 0.000 claims description 8
239000003826 tablet Substances 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
239000002775 capsule Substances 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
UUMQGMCYAJYYQR-UHFFFAOYSA-N 4-chloro-5-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propylamino]-1h-pyridazin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCNC1=C(Cl)C=NNC1=O UUMQGMCYAJYYQR-UHFFFAOYSA-N 0.000 claims description 5
239000000969 carrier Substances 0.000 claims description 5
239000007937 lozenge Substances 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
-1 sachets Substances 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
239000000010 aprotic solvent Substances 0.000 claims description 4
239000000839 emulsion Substances 0.000 claims description 4
239000012454 non-polar solvent Substances 0.000 claims description 4
239000000829 suppository Substances 0.000 claims description 4
239000003416 antiarrhythmic agent Substances 0.000 claims description 3
150000008282 halocarbons Chemical class 0.000 claims description 3
239000006187 pill Substances 0.000 claims description 3
230000005855 radiation Effects 0.000 claims description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
229910016523 CuKa Inorganic materials 0.000 claims description 2
238000004090 dissolution Methods 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
239000003586 protic polar solvent Substances 0.000 claims description 2
239000007921 spray Substances 0.000 claims description 2
230000003288 anthiarrhythmic effect Effects 0.000 claims 1
238000003756 stirring Methods 0.000 description 20
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
239000013078 crystal Substances 0.000 description 13
239000000047 product Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 9
238000009835 boiling Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
URHMBHUFCQCLKG-WLHGVMLRSA-N (e)-but-2-enedioic acid;1h-pyridazin-6-one Chemical compound O=C1C=CC=NN1.OC(=O)\C=C\C(O)=O URHMBHUFCQCLKG-WLHGVMLRSA-N 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000001993 wax Substances 0.000 description 3
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
STGNLGBPLOVYMA-MAZDBSFSSA-N (E)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O STGNLGBPLOVYMA-MAZDBSFSSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VJWXIRQLLGYIDI-UHFFFAOYSA-N 4,5-dichloro-1h-pyridazin-6-one Chemical compound OC1=NN=CC(Cl)=C1Cl VJWXIRQLLGYIDI-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
206010003658 Atrial Fibrillation Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
235000021311 artificial sweeteners Nutrition 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000005284 excitation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
229920000591 gum Polymers 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
JWANNLXCVGJLAS-UHFFFAOYSA-N n'-[2-(3,4-dimethoxyphenyl)ethyl]-n'-methylpropane-1,3-diamine Chemical compound COC1=CC=C(CCN(C)CCCN)C=C1OC JWANNLXCVGJLAS-UHFFFAOYSA-N 0.000 description 1
235000021096 natural sweeteners Nutrition 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000000634 powder X-ray diffraction Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
208000003663 ventricular fibrillation Diseases 0.000 description 1
239000011345 viscous material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/22—Nitrogen and oxygen atoms
- 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
- 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
- A61P9/06—Antiarrhythmics

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Treating Waste Gases (AREA)
Photoreceptors In Electrophotography (AREA)
Silver Salt Photography Or Processing Solution Therefor (AREA)

SK54-2004A 2001-07-26 2002-07-26 Polymorph salt of a pyridazinone derivative for the treatment arrhythmia SK542004A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU0103064A HUP0103064A3 (en)	2001-07-26	2001-07-26	Polymorphic form of 5-chloro-4-(3-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino]-propylamino)-3-(2h)-piridazinone fumarate, its use, process for its preparation and pharmaceutical compositions containing it
PCT/HU2002/000076 WO2003010150A1 (en)	2001-07-26	2002-07-26	Polymorph salt of a pyridazinone derivative for the treatment of arrythmia

Publications (1)

Publication Number	Publication Date
SK542004A3 true SK542004A3 (en)	2004-08-03

Family

ID=89979563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK54-2004A SK542004A3 (en)	2001-07-26	2002-07-26	Polymorph salt of a pyridazinone derivative for the treatment arrhythmia

Country Status (15)

Country	Link
US (1)	US20040266772A1 (cs)
EP (1)	EP1417179A1 (cs)
JP (1)	JP2004536868A (cs)
KR (1)	KR20040030861A (cs)
CN (1)	CN1545505A (cs)
CA (1)	CA2454774A1 (cs)
CZ (1)	CZ2004124A3 (cs)
EA (1)	EA200400222A1 (cs)
HU (1)	HUP0103064A3 (cs)
IL (1)	IL159967A0 (cs)
PL (1)	PL365483A1 (cs)
SK (1)	SK542004A3 (cs)
WO (1)	WO2003010150A1 (cs)
YU (1)	YU7604A (cs)
ZA (1)	ZA200400483B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU227181B1 (en) *	2002-09-11	2010-09-28	Egis Gyogyszergyar Nyilvanosan	Use of 5-chloro-4-[3-[n-[2-(3,4-dimethoxyphenyl)ethyl)]-n-methylamino]-propylamino]-3-(2h)-pyridazinone for producing pharmaceutical compositions having metabolic modulator effect
HU227115B1 (en) *	2003-10-10	2010-07-28	Egis Gyogyszergyar Nyilvanosan	Pellets containing pyridazinone derivative
GB201105537D0 (en) *	2011-03-31	2011-05-18	Vantia Ltd	New process

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU214320B (hu) *	1991-12-20	1998-03-02	EGIS Gyógyszergyár Rt.	Eljárás új 3(2H)-piridazinon-származékok és ezeket tartalmazó gyógyszerkészítmények előállítására
JP2004500314A (ja) *	1998-06-05	2004-01-08	エギシュ　ヂョヂセルヂャール　エルテー	３（２ｈ）−ピリダジノン−４−置換アミノ−５−クロロ−誘導体の製法

2001
- 2001-07-26 HU HU0103064A patent/HUP0103064A3/hu unknown
2002
- 2002-07-26 IL IL15996702A patent/IL159967A0/xx unknown
- 2002-07-26 YU YU7604A patent/YU7604A/sh unknown
- 2002-07-26 KR KR10-2004-7001150A patent/KR20040030861A/ko not_active Withdrawn
- 2002-07-26 SK SK54-2004A patent/SK542004A3/sk not_active Application Discontinuation
- 2002-07-26 WO PCT/HU2002/000076 patent/WO2003010150A1/en not_active Ceased
- 2002-07-26 US US10/484,621 patent/US20040266772A1/en not_active Abandoned
- 2002-07-26 CZ CZ2004124A patent/CZ2004124A3/cs unknown
- 2002-07-26 EA EA200400222A patent/EA200400222A1/ru unknown
- 2002-07-26 CA CA002454774A patent/CA2454774A1/en not_active Abandoned
- 2002-07-26 CN CNA028162587A patent/CN1545505A/zh active Pending
- 2002-07-26 PL PL02365483A patent/PL365483A1/xx unknown
- 2002-07-26 EP EP02755384A patent/EP1417179A1/en not_active Withdrawn
- 2002-07-26 JP JP2003515509A patent/JP2004536868A/ja active Pending
2004
- 2004-01-22 ZA ZA200400483A patent/ZA200400483B/en unknown

Also Published As

Publication number	Publication date
EP1417179A1 (en)	2004-05-12
WO2003010150A1 (en)	2003-02-06
CZ2004124A3 (cs)	2004-06-16
PL365483A1 (en)	2005-01-10
HUP0103064A2 (hu)	2003-02-28
HUP0103064A3 (en)	2005-06-28
ZA200400483B (en)	2005-04-22
CN1545505A (zh)	2004-11-10
YU7604A (sh)	2006-08-17
EA200400222A1 (ru)	2004-12-30
KR20040030861A (ko)	2004-04-09
JP2004536868A (ja)	2004-12-09
IL159967A0 (en)	2004-06-20
US20040266772A1 (en)	2004-12-30
HU0103064D0 (en)	2001-10-28
CA2454774A1 (en)	2003-02-06

Legal Events

Date	Code	Title	Description
2011-11-04	FC9A	Refused patent application

Publication	Publication Date	Title
RU2186765C2 (ru)	2002-08-10	Кристаллические модификации 2-амино-4-(4-фторбензиламино)-1-этоксикарбонил-аминобензола и способ их получения (варианты)
KR20080015888A (ko)	2008-02-20	카르베딜올
CZ200426A3 (cs)	2004-04-14	Název neuveden
HU210780B (en)	1995-07-28	Process for producing pyrimidindione derivatives and pharmaceutical compositions containing them as active components
NZ243959A (en)	1995-07-26	Substituted pyrazine derivatives and pharmaceutical compositions thereof
JPH04230681A (ja)	1992-08-19	１，４‐ベンゾチアゼピン誘導体
US11786498B2 (en)	2023-10-17	Sacubitril calcium salts
HU213212B (en)	1997-03-28	Process for producing acid additional salts of 4-amino-2-ureidopyrimidine-5-carboxylic acid amide derivatives and pharmaceutical compositions comprising the same
JPH05271208A (ja)	1993-10-19	１，４‐ベンゾチアゼピン誘導体
CZ2004124A3 (cs)	2004-06-16	Název neuveden
KR20190064589A (ko)	2019-06-10	4-(2-((1r,2r)-2-히드록시시클로헥실아미노)벤조티아졸-6-일옥시)-n-메틸피콜린아미드의 결정질 형태
US4206217A (en)	1980-06-03	3-[4-(1,3-Diazacycloalken-2-yl)-phenyl]-1,2-benzisothiazoles, their manufacture, and drugs containing these compounds
US4486431A (en)	1984-12-04	Cardiotonic use of 4,5-dihydro-6-(4-pyridinyl)-3(2H)-pyridazinones
KR880000729B1 (ko)	1988-04-29	아닐리노-1, 2, 3-트리아졸 유도체의 제조방법
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