DK174097B1 - 2-Substituerede 5-alkoxy-4(1H)-pyridonderivater og farmakologisk accepteble salte deraf, fremgangsmåde til fremstilling deraf, farmaceutisk præparat samt derivaternes anvendelse - Google Patents

2-Substituerede 5-alkoxy-4(1H)-pyridonderivater og farmakologisk accepteble salte deraf, fremgangsmåde til fremstilling deraf, farmaceutisk præparat samt derivaternes anvendelse Download PDF

Info

Publication number: DK174097B1
Authority: DK; Denmark
Prior art keywords: group; carbon atoms; general formula; pyridone; phenyl
Prior art date: 1988-08-06

Application number

DK199100113A

Other languages

Danish (da)

English (en)

Other versions

DK11391D0 (da

DK11391A (da

Inventor

Johannes Hartenstein

Hartmut Osswald

Guenter Weinheimer

Christoph Schaechtele

Claus Rudolph

Julian Aranda

Reinhard Reck

Original Assignee

Goedecke Ag

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.)

1988-08-06

Filing date

1991-01-23

Publication date

2002-06-10

1991-01-23 Application filed by Goedecke Ag filed Critical Goedecke Ag

1991-01-23 Publication of DK11391D0 publication Critical patent/DK11391D0/da

1991-01-23 Publication of DK11391A publication Critical patent/DK11391A/da

2002-06-10 Application granted granted Critical

2002-06-10 Publication of DK174097B1 publication Critical patent/DK174097B1/da

Links

238000000034 method Methods 0.000 title claims abstract description 16
150000003839 salts Chemical class 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 10
239000000825 pharmaceutical preparation Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 64
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
206010020751 Hypersensitivity Diseases 0.000 claims abstract description 3
206010028980 Neoplasm Diseases 0.000 claims abstract description 3
230000007815 allergy Effects 0.000 claims abstract description 3
230000004054 inflammatory process Effects 0.000 claims abstract description 3
210000003169 central nervous system Anatomy 0.000 claims abstract 2
230000002265 prevention Effects 0.000 claims abstract 2
125000004432 carbon atom Chemical group C* 0.000 claims description 56
-1 hydroxy, methyl Chemical group 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
229920006395 saturated elastomer Polymers 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
125000003884 phenylalkyl group Chemical group 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical group 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004663 dialkyl amino group Chemical group 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 4
PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
MVKDNXIKAWKCCS-UHFFFAOYSA-N 3-methyl-1h-pyridin-2-one Chemical compound CC1=CC=CN=C1O MVKDNXIKAWKCCS-UHFFFAOYSA-N 0.000 claims description 2
208000024172 Cardiovascular disease Diseases 0.000 claims description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 3
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
239000002671 adjuvant Substances 0.000 claims 1
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229940030850 avar Drugs 0.000 claims 1
125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 1
125000004803 chlorobenzyl group Chemical group 0.000 claims 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
230000007850 degeneration Effects 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000006289 hydroxybenzyl group Chemical group 0.000 claims 1
125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
125000006178 methyl benzyl group Chemical group 0.000 claims 1
239000012038 nucleophile Substances 0.000 claims 1
125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 124
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 72
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
239000000243 solution Substances 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
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238000006243 chemical reaction Methods 0.000 description 23
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HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 14
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ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
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230000000694 effects Effects 0.000 description 11
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
230000001419 dependent effect Effects 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
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SWHWWDQVLJPUDV-UHFFFAOYSA-N 2-(hydroxymethyl)-5-octadecoxypyran-4-one Chemical compound CCCCCCCCCCCCCCCCCCOC1=COC(CO)=CC1=O SWHWWDQVLJPUDV-UHFFFAOYSA-N 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- A61P9/10—Drugs 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
- 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
- A61P9/12—Antihypertensives
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (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)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Immunology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

DK199100113A 1988-08-06 1991-01-23 2-Substituerede 5-alkoxy-4(1H)-pyridonderivater og farmakologisk accepteble salte deraf, fremgangsmåde til fremstilling deraf, farmaceutisk præparat samt derivaternes anvendelse DK174097B1 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE3826846A DE3826846A1 (de)	1988-08-06	1988-08-06	Alkoxy-4(1h)-pyridon-derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel
DE3826846		1988-08-06
EP8900927		1989-08-04
PCT/EP1989/000927 WO1990001477A1 (fr)	1988-08-06	1989-08-04	Derives d'alkoxy-4(1h)-pyridone, leurs procedes de preparation et leur emploi comme medicaments

Publications (3)

Publication Number	Publication Date
DK11391D0 DK11391D0 (da)	1991-01-23
DK11391A DK11391A (da)	1991-01-23
DK174097B1 true DK174097B1 (da)	2002-06-10

Family

ID=6360419

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK199100113A DK174097B1 (da)	1988-08-06	1991-01-23	2-Substituerede 5-alkoxy-4(1H)-pyridonderivater og farmakologisk accepteble salte deraf, fremgangsmåde til fremstilling deraf, farmaceutisk præparat samt derivaternes anvendelse

Country Status (18)

Country	Link
US (2)	US5185352A (fr)
EP (2)	EP0427765B1 (fr)
JP (1)	JP2878361B2 (fr)
KR (1)	KR920006779B1 (fr)
CN (1)	CN1040193A (fr)
AT (1)	ATE188469T1 (fr)
AU (1)	AU627766B2 (fr)
CA (1)	CA1340608C (fr)
DD (1)	DD284003A5 (fr)
DE (2)	DE3826846A1 (fr)
DK (1)	DK174097B1 (fr)
ES (1)	ES2144391T3 (fr)
GR (1)	GR3033072T3 (fr)
HU (1)	HUT56545A (fr)
NO (1)	NO177785C (fr)
PT (1)	PT91351B (fr)
WO (1)	WO1990001477A1 (fr)
ZA (1)	ZA895969B (fr)

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US5674883A (en) *	1992-02-07	1997-10-07	Roussel Uclaf	Derivatives of pyridone, their preparation process, the new intermediates obtained, their use as medicaments and the pharmaceutical compositions containing them
DE4243321A1 (de) *	1992-12-21	1994-06-23	Goedecke Ag	Aminosäurederivate von Heterocyclen als PKC-Inhibitoren
US6046219A (en) *	1995-01-20	2000-04-04	Cornell Research Foundation, Inc.	Method for the treatment of conditions mediated by collagen formation together with cell proliferation by application of inhibitors of protein hydroxylation
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GB2321455A (en) *	1997-01-24	1998-07-29	Norsk Hydro As	Lipophilic derivatives of biologically active compounds
JP2002531512A (ja) *	1998-12-07	2002-09-24	エコスマートテクノロジーズ，インコーポレーテッド	天然植物精油を用いた癌治療薬配合物および方法
US6867217B1 (en)	1999-05-19	2005-03-15	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl pyridones useful for selective inhibition of the coagulation cascade
US6906068B1 (en)	1999-05-19	2005-06-14	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl 1,2,4 - triazinones useful as anticoagulants
US6750342B1 (en)	1999-05-19	2004-06-15	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade
US6664255B1 (en)	1999-05-19	2003-12-16	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl pyrazinones useful for selective inhibition of the coagulation cascade
US6653316B1 (en)	1999-05-19	2003-11-25	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade
US6716838B1 (en)	1999-05-19	2004-04-06	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl uracils as anticoagulative agents
US7015230B1 (en)	1999-05-19	2006-03-21	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl uracils useful for selective inhibition of the coagulation cascade
WO2001068605A1 (fr)	2000-03-13	2001-09-20	Pharmacia Corporation	Benzenes polycycliques substitues aryle et heteroaryle utiles pour l'inhibition selective de la cascade de coagulation
WO2001077097A2 (fr)	2000-04-05	2001-10-18	Pharmacia Corporation	4-pyrones polycycliques a substitution aryle et heteroaryle utiles pour l'inhibition selective de la cascade de coagulation
CA2405306A1 (fr)	2000-04-05	2001-10-18	Pharmacia Corporation	Pyridones polycycliques 4-aryl et heteroaryl substituees utiles pour l'inhibition selective de la cascade de coagulation
US7119094B1 (en)	2000-11-20	2006-10-10	Warner-Lambert Company	Substituted polycyclic aryl and heteroarpyl pyrazinones useful for selective inhibition of the coagulation cascade
US7015223B1 (en)	2000-11-20	2006-03-21	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl 1,2,4-triazinones useful for selective inhibition of the coagulation cascade
CA2430037A1 (fr)	2000-11-20	2002-05-30	Michael S. South	Aryl-et-heteroaryl-pyridines polycycliques substituees utiles dans l'inhibition selective de la cascade de la coagulation
BR0213092A (pt)	2001-10-03	2004-10-19	Pharmacia Corp	Compostos heterocìclicos de 6 elementos úteis para a inibição seletiva da cascata de coagulação
US7105559B2 (en)	2001-10-03	2006-09-12	Pharmacia Corporation	Substituted 5-membered polycyclic compounds useful for selective inhibition of the coagulation cascade
CA2627529A1 (fr)	2007-03-28	2008-09-28	Apotex Technologies Inc.	Derives fluores de deferiprone
BRPI0822206B8 (pt)	2008-04-25	2021-05-25	Apotex Tech Inc	formulação líquida para deferiprona com um sabor agradável.
BRPI1007636A2 (pt)	2009-05-01	2015-09-01	Aptalis Pharmatech Inc	Composição farmacêutica, forma de dosagem, método para a preparação da composição farmacêutica, método de preparação da forma de dosagem e método de tratamento da dor
EP2448922B1 (fr) *	2009-07-03	2014-08-20	Apotex Technologies Inc.	Dérivés fluorés de 3-hydroxypyridin-4-ones
CN107709299B (zh)	2015-04-24	2021-07-16	盐野义制药株式会社	6元杂环衍生物及含有其的药物组合物
JP6692113B2 (ja) *	2016-10-21	2020-05-13	塩野義製薬株式会社	６員複素環誘導体を含有する医薬組成物

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CA554715A (fr) *		1958-03-18	Boesch Roger	Ethers et thioethers et procede pour leur fabrication
US2965641A (en) *	1959-07-06	1960-12-20	Searle & Co	Derivatives of 1-(2-aminoethyl)-5-alkoxy-4-pyridones
CA978958A (en) *	1971-10-04	1975-12-02	Haydn W.R. Williams	Substituted pyranones and -pyridones and process of manufacture
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JPS59110674A (ja) *	1982-12-16	1984-06-26	Ss Pharmaceut Co Ltd	ピリジン誘導体及びその製造法
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CA1283404C (fr) *	1986-07-01	1991-04-23	Shigeru Sanai	Composes de cephalosporine, procede de preparation et agents antibacteriens
DE3826846A1 (de) *	1988-08-06	1990-02-08	Goedecke Ag	Alkoxy-4(1h)-pyridon-derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel

1988
- 1988-08-06 DE DE3826846A patent/DE3826846A1/de not_active Ceased
1989
- 1989-08-02 DD DD89331409A patent/DD284003A5/de not_active IP Right Cessation
- 1989-08-02 PT PT91351A patent/PT91351B/pt not_active IP Right Cessation
- 1989-08-04 JP JP1508466A patent/JP2878361B2/ja not_active Expired - Fee Related
- 1989-08-04 CA CA000607563A patent/CA1340608C/fr not_active Expired - Fee Related
- 1989-08-04 EP EP89908987A patent/EP0427765B1/fr not_active Expired - Lifetime
- 1989-08-04 DE DE58909865T patent/DE58909865D1/de not_active Expired - Fee Related
- 1989-08-04 KR KR1019900700696A patent/KR920006779B1/ko not_active Expired
- 1989-08-04 ZA ZA895969A patent/ZA895969B/xx unknown
- 1989-08-04 EP EP89114477A patent/EP0354495A1/fr active Pending
- 1989-08-04 HU HU894581A patent/HUT56545A/hu unknown
- 1989-08-04 US US07/640,407 patent/US5185352A/en not_active Expired - Lifetime
- 1989-08-04 AU AU40489/89A patent/AU627766B2/en not_active Ceased
- 1989-08-04 ES ES89908987T patent/ES2144391T3/es not_active Expired - Lifetime
- 1989-08-04 WO PCT/EP1989/000927 patent/WO1990001477A1/fr not_active Ceased
- 1989-08-04 AT AT89908987T patent/ATE188469T1/de not_active IP Right Cessation
- 1989-08-05 CN CN89105574A patent/CN1040193A/zh active Pending
1991
- 1991-01-23 DK DK199100113A patent/DK174097B1/da not_active IP Right Cessation
- 1991-02-05 NO NO910444A patent/NO177785C/no unknown
1992
- 1992-10-07 US US07/957,937 patent/US5322844A/en not_active Expired - Fee Related
2000
- 2000-03-27 GR GR20000400761T patent/GR3033072T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR920006779B1 (ko)	1992-08-17
AU4048989A (en)	1990-03-05
NO177785B (no)	1995-08-14
DD284003A5 (de)	1990-10-31
EP0354495A1 (fr)	1990-02-14
HU894581D0 (en)	1991-07-29
JPH04500958A (ja)	1992-02-20
DE58909865D1 (de)	2000-02-10
DK11391D0 (da)	1991-01-23
ATE188469T1 (de)	2000-01-15
NO910444L (no)	1991-02-05
NO177785C (no)	1995-11-22
EP0427765A1 (fr)	1991-05-22
CN1040193A (zh)	1990-03-07
ES2144391T3 (es)	2000-06-16
CA1340608C (fr)	1999-06-22
WO1990001477A1 (fr)	1990-02-22
KR900701755A (ko)	1990-12-04
US5185352A (en)	1993-02-09
NO910444D0 (no)	1991-02-05
PT91351A (pt)	1990-03-08
JP2878361B2 (ja)	1999-04-05
HUT56545A (en)	1991-09-30
DK11391A (da)	1991-01-23
PT91351B (pt)	1997-01-31
AU627766B2 (en)	1992-09-03
ZA895969B (en)	1990-05-30
DE3826846A1 (de)	1990-02-08
GR3033072T3 (en)	2000-08-31
EP0427765B1 (fr)	2000-01-05
US5322844A (en)	1994-06-21

Publication	Publication Date	Title
DK174097B1 (da)	2002-06-10	2-Substituerede 5-alkoxy-4(1H)-pyridonderivater og farmakologisk accepteble salte deraf, fremgangsmåde til fremstilling deraf, farmaceutisk præparat samt derivaternes anvendelse
US5679688A (en)	1997-10-21	Quinaldoyl-amine derivatives of oxo-and hydroxy-substituted hydrocarbons
US4933447A (en)	1990-06-12	Quinoline derivatives
JPS61155358A (ja)	1986-07-15	ジアリール酪酸誘導体
FR2518994A1 (fr)	1983-07-01	2-(4-(4,4-dialkyl-2,6-piperidinedion-1-yl) butyl)-1-pyperazinyl) pyridines et leur application pharmacologique
FI66373B (fi)	1984-06-29	Foerfarande foer framstaellning av farmakologiskt verksamma n-xacyklyl-alkyl-piperidiner
US5594144A (en)	1997-01-14	Tropolone derivatives and pharmaceutical composition thereof for preventing and treating ischemic diseases
HU207295B (en)	1993-03-29	Process for producing pyridine-2,4- and 2,5-dicarboxylic acid derivatives and pharmaceutical compositions containing them
JP3994453B2 (ja)	2007-10-17	ピラゾロン類
JP3053418B2 (ja)	2000-06-19	新規の置換アルキルピペリジンとコレステロール合成阻害剤としてのその用途
CA2179735A1 (fr)	1995-06-29	N-oxydes de 4-arylepiperazines et 4-arylpiperidines utilises comme medicaments neuroleptiques
US3072648A (en)	1963-01-08	X-phenyl-s
US5356922A (en)	1994-10-18	Imidazole compounds, processes for their preparation, pharmaceuticals based on these compounds and some intermediates
US5166157A (en)	1992-11-24	Naphthyl piperazines useful as 5-HT1A receptor ligands
FI62531C (fi)	1983-01-10	Foerfarande foer framstaellning av terapeutiskt anvaendbart 3-yan-n-(n n-dimetylamino-propyl)-iminodibensyl och syraadd itonssalter daerav
US4337253A (en)	1982-06-29	4,5-Dihydro-2-methyl-6-(4-pyridinyl)-3(2H)-pyridazinone and its use as a cardiotonic
JPH0459754A (ja)	1992-02-26	アミド誘導体
US3128279A (en)	1964-04-07	Diphenylmethane derivatives and methods for the preparation thereof
WO1998031671A1 (fr)	1998-07-23	Derives de pyridone, leur preparation et leur utilisation comme intermediaires de synthese
KR100824831B1 (ko)	2008-04-23	다치환된 1,1-피리딜아미노시클로프로판아민 화합물, 이의제조 방법, 및 이를 함유하는 약제 조성물
DE69615669T2 (de)	2002-07-11	Piperidenyl-2-alkyl substituierte lineare polyamine zur senkung intrazellulärer, endogener polyaminkonzentrationen wie z.b. putrescin, spermidin und spermin und ihr einfluss auf die zellvermehrung
IL96144A (en)	1994-06-24	Pharmaceutical compositions containing (n-phthalimidoalkyl)- piperidines, certain such novel compounds and their preparation
JPH0253780A (ja)	1990-02-22	Δ↑２‐１，２，４‐トリアゾリン‐５‐オン誘導体、その製造法およびそれを有効成分とする抗潰瘍剤
PT97885B (pt)	1998-10-30	Processo para a preparacao de derivados da {(1-aril-2-pirrolidinil)-metil-piperazina e de composicoes farmaceuticas que os contem
JP3930081B2 (ja)	2007-06-13	２−ウレイド−ベンズアミド誘導体

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Date	Code	Title	Description
2002-06-10	B1	Patent granted (law 1993)
2006-04-18	PBP	Patent lapsed	Country of ref document: DK