DE10229070A1 - Phenylderivate 5 - Google Patents
Phenylderivate 5 Download PDFInfo
- Publication number
- DE10229070A1 DE10229070A1 DE10229070A DE10229070A DE10229070A1 DE 10229070 A1 DE10229070 A1 DE 10229070A1 DE 10229070 A DE10229070 A DE 10229070A DE 10229070 A DE10229070 A DE 10229070A DE 10229070 A1 DE10229070 A1 DE 10229070A1
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- Prior art keywords
- diyl
- formula
- imino
- phenyl
- compounds
- Prior art date
- 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.)
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 19
- -1 Aromatic amidine Chemical class 0.000 description 260
- 150000001875 compounds Chemical class 0.000 description 69
- 125000004432 carbon atom Chemical group C* 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 23
- 125000002947 alkylene group Chemical group 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 125000004430 oxygen atom Chemical group O* 0.000 description 16
- 125000006239 protecting group Chemical group 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- 125000004434 sulfur atom Chemical group 0.000 description 14
- 108010074860 Factor Xa Proteins 0.000 description 13
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- 229910052801 chlorine Inorganic materials 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- 206010028980 Neoplasm Diseases 0.000 description 12
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
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- 125000003118 aryl group Chemical group 0.000 description 11
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
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- 239000000126 substance Substances 0.000 description 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- 108010054265 Factor VIIa Proteins 0.000 description 7
- 125000002252 acyl group Chemical class 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
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- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- WFACJPXQZKUMMZ-UHFFFAOYSA-N 2-(3-carbamoylphenyl)-5-(trifluoromethyl)pyrazole-3-carboxylic acid Chemical compound NC(=O)C1=CC=CC(N2C(=CC(=N2)C(F)(F)F)C(O)=O)=C1 WFACJPXQZKUMMZ-UHFFFAOYSA-N 0.000 description 5
- 108010048049 Factor IXa Proteins 0.000 description 5
- 208000006011 Stroke Diseases 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 238000002399 angioplasty Methods 0.000 description 5
- 230000002785 anti-thrombosis Effects 0.000 description 5
- 229940127219 anticoagulant drug Drugs 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229940012414 factor viia Drugs 0.000 description 5
- 125000001634 furandiyl group Chemical group O1C(=C(C=C1)*)* 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 208000010125 myocardial infarction Diseases 0.000 description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000000464 thioxo group Chemical group S=* 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
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- AMUXDCKKFCHHLY-UHFFFAOYSA-N 2-[3-(aminomethyl)phenyl]-5-(trifluoromethyl)pyrazole-3-carboxylic acid Chemical compound NCC1=CC=CC(N2C(=CC(=N2)C(F)(F)F)C(O)=O)=C1 AMUXDCKKFCHHLY-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- NNMUGYYWXZBGBW-UHFFFAOYSA-N tert-butyl 2-(aminomethyl)-3-[5-[[4-(2-methylsulfanylpyrrolidin-1-yl)phenyl]carbamoyl]-3-(trifluoromethyl)pyrazol-1-yl]benzoate Chemical compound CSC1CCCN1C(C=C1)=CC=C1NC(=O)C1=CC(C(F)(F)F)=NN1C1=CC=CC(C(=O)OC(C)(C)C)=C1CN NNMUGYYWXZBGBW-UHFFFAOYSA-N 0.000 description 1
- QKWILGMTCNWFJK-UHFFFAOYSA-N tert-butyl n-[[3-[5-[[4-(2-iminopyrrolidin-1-yl)phenyl]carbamoyl]-3-(trifluoromethyl)pyrazol-1-yl]phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(N2C(=CC(=N2)C(F)(F)F)C(=O)NC=2C=CC(=CC=2)N2C(CCC2)=N)=C1 QKWILGMTCNWFJK-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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- 125000005425 toluyl group Chemical group 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
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- A—HUMAN NECESSITIES
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10229070A DE10229070A1 (de) | 2002-06-28 | 2002-06-28 | Phenylderivate 5 |
| CA002491271A CA2491271A1 (en) | 2002-06-28 | 2003-06-05 | 2-(phenyl)-2h-pyrazole-3-carboxylic acid-n-4-(thioxo-heterocyclyl)-phenyl-amide derivatives and corresponding imino-heterocyclyl derivatives and relates compounds for use as inhibitors of the coagulation factors xa and/or viia for treating thromboses |
| JP2004516575A JP2005535630A (ja) | 2002-06-28 | 2003-06-05 | ２−（フェニル）−２Ｈ−ピラゾール−３−カルボン酸−Ｎ−４−（チオキソ−ヘテロサイクル）−フェニル−アミド誘導体、ならびに対応するイミノ−ヘテロサイクル誘導体、および関連する化合物の、凝固因子Ｘａおよび／またはＶＩＩａの阻害剤として、血栓症の治療のための使用 |
| EP03732540A EP1517685A1 (de) | 2002-06-28 | 2003-06-05 | 2-(phenyl)-2h-pyrazol-3-carbonsäure-n-4-(thioxo-heterocyclyl)-phenyl-amid derivate und entsprechende imino-heterocyclyl derivate sowie verwandte verbindungen als inhibitoren der koagulationsfaktoren xa und/oder viia zur behandlung von thrombosen |
| AU2003238475A AU2003238475A1 (en) | 2002-06-28 | 2003-06-05 | 2-(phenyl)-2h-pyrazole-3-carboxylic acid-n-4-(thioxo-heterocyclyl)-phenyl-amide derivatives and corresponding imino-heterocyclyl derivatives and relates compounds for use as inhibitors of the coagulation factors xa and/or viia for treating thromboses |
| US10/519,356 US20050203127A1 (en) | 2002-06-28 | 2003-06-05 | 2-(Phenyl)-2h-pyrazole-3-carboxylic acid-n-4-(thioxo-heterocyclyl)-phenyl-amide derivatives and corresponding imino-heterocyclyl derivatives and relates compounds for use as inhibitors of the coagulation factors xa and/or viia for treating thromboses |
| PCT/EP2003/005898 WO2004002477A1 (de) | 2002-06-28 | 2003-06-05 | 2-(phenyl)-2h-pyrazol-3-carbonsäure-n-4-(thioxo-heterocyclyl)-phenyl-amid derivate und entsprechende imino-heterocyclyl derivate sowie verwandte verbindungen als inhibitoren der koagulationsfaktoren xa und/oder viia zur behandlung bon thrombosen |
| EP06000157A EP1679073A1 (de) | 2002-06-28 | 2003-06-05 | 2-(PHENYL)-2H-PYRAZOL-3-CARBONSÄURE-N-4-(IMINO-HETEROCYCLYL)-PHENYL-AMID DERIVATE SOWIE VERWANDTE VERBINDUNGEN ALS INHIBITOREN DER KOAGULATIONSFAKTOREN XA UND/ODER VIIA ZUR BEHANDLUNG VON THROMBOSENPhenylderivate 5 |
| AR20030102321A AR040472A1 (es) | 2002-06-28 | 2003-06-27 | Derivado de 2-(fenil)-2h-pirazol-3-carboxilico-n-4(tioxo-heterociclil)fenil-amida e imino-heterociclil derivados y compuestos relacionados, procedimiento, medicamentos, kit |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10229070A DE10229070A1 (de) | 2002-06-28 | 2002-06-28 | Phenylderivate 5 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10229070A1 true DE10229070A1 (de) | 2004-01-15 |
Family
ID=29723536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10229070A Withdrawn DE10229070A1 (de) | 2002-06-28 | 2002-06-28 | Phenylderivate 5 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20050203127A1 (https=) |
| EP (2) | EP1679073A1 (https=) |
| JP (1) | JP2005535630A (https=) |
| AR (1) | AR040472A1 (https=) |
| AU (1) | AU2003238475A1 (https=) |
| CA (1) | CA2491271A1 (https=) |
| DE (1) | DE10229070A1 (https=) |
| WO (1) | WO2004002477A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002006234A1 (en) * | 2000-07-17 | 2002-01-24 | Takeda Chemical Industries, Ltd. | Sulfone derivatives, process for their production and use thereof |
| AU2003284596A1 (en) * | 2002-11-22 | 2004-06-18 | Takeda Pharmaceutical Company Limited | Imidazole derivative, process for producing the same, and use |
| TWI396686B (zh) * | 2004-05-21 | 2013-05-21 | Takeda Pharmaceutical | 環狀醯胺衍生物、以及其製品和用法 |
| DE102004051277A1 (de) * | 2004-10-21 | 2006-04-27 | Merck Patent Gmbh | Heterocyclische Carbonylverbindungen |
| US7446210B2 (en) | 2004-10-26 | 2008-11-04 | Janssen Pharmaceutica N.V. | Factor Xa compounds |
| DE102005038947A1 (de) | 2005-05-18 | 2006-11-30 | Grünenthal GmbH | Substituierte Benzo[d]isoxazol-3-yl-amin-Verbindungen und deren Verwendung in Arzneimitteln |
| DE102005045115A1 (de) * | 2005-09-21 | 2007-04-05 | Siemens Ag | Verfahren und Vorrichtung zum Betrieb eines Kommunikationsendgeräts |
| US8338367B2 (en) | 2008-10-15 | 2012-12-25 | Boehringer Ingelheim International Gmbh | Fused heteroaryl diamide compounds useful as MMP-13 inhibitors |
| US8785489B2 (en) | 2008-10-17 | 2014-07-22 | Boehringer Ingelheim International Gmbh | Heteroaryl substituted indole compounds useful as MMP-13 inhibitors |
| JP6155187B2 (ja) | 2010-03-30 | 2017-06-28 | ヴァーセオン コーポレイション | トロンビンの阻害剤としての多置換芳香族化合物 |
| HK1214252A1 (zh) | 2013-03-15 | 2016-07-22 | Verseon Corporation | 作為凝血酶抑制劑的鹵代吡唑 |
| CN110179795A (zh) | 2013-03-15 | 2019-08-30 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的多取代芳族化合物的制药用途 |
| JP6223563B2 (ja) | 2013-10-14 | 2017-11-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 選択的に置換されたキノリン化合物 |
| CN105636945B (zh) | 2013-10-14 | 2017-11-17 | 卫材R&D管理有限公司 | 选择性取代的喹啉化合物 |
| CN106257976B (zh) | 2014-03-07 | 2021-02-02 | 拜奥克里斯特制药公司 | 人类血浆激肽释放酶抑制剂 |
| US10189810B2 (en) | 2014-09-17 | 2019-01-29 | Verseon Corporation | Pyrazolyl-substituted pyridone compounds as serine protease inhibitors |
| CN107405333A (zh) | 2015-02-27 | 2017-11-28 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的被取代的吡唑化合物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1246847A (zh) * | 1996-12-23 | 2000-03-08 | 杜邦药品公司 | 作为Xa因子抑制剂的含氮杂芳族化合物 |
| US6020357A (en) * | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| KR20010013977A (ko) * | 1997-06-19 | 2001-02-26 | 블레어 큐. 퍼거슨 | 중성 ｐ1 특이성 기를 갖는 인자 ｘａ의 억제제 |
| ZA985247B (en) * | 1997-06-19 | 1999-12-17 | Du Pont Merck Pharma | Guanidine mimics as factor Xa inhibitors. |
| US5998424A (en) * | 1997-06-19 | 1999-12-07 | Dupont Pharmaceuticals Company | Inhibitors of factor Xa with a neutral P1 specificity group |
-
2002
- 2002-06-28 DE DE10229070A patent/DE10229070A1/de not_active Withdrawn
-
2003
- 2003-06-05 EP EP06000157A patent/EP1679073A1/de not_active Withdrawn
- 2003-06-05 US US10/519,356 patent/US20050203127A1/en not_active Abandoned
- 2003-06-05 JP JP2004516575A patent/JP2005535630A/ja active Pending
- 2003-06-05 AU AU2003238475A patent/AU2003238475A1/en not_active Abandoned
- 2003-06-05 CA CA002491271A patent/CA2491271A1/en not_active Abandoned
- 2003-06-05 EP EP03732540A patent/EP1517685A1/de not_active Withdrawn
- 2003-06-05 WO PCT/EP2003/005898 patent/WO2004002477A1/de not_active Ceased
- 2003-06-27 AR AR20030102321A patent/AR040472A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR040472A1 (es) | 2005-04-06 |
| EP1517685A1 (de) | 2005-03-30 |
| WO2004002477A8 (de) | 2004-04-15 |
| CA2491271A1 (en) | 2004-01-08 |
| JP2005535630A (ja) | 2005-11-24 |
| US20050203127A1 (en) | 2005-09-15 |
| WO2004002477A1 (de) | 2004-01-08 |
| EP1679073A1 (de) | 2006-07-12 |
| AU2003238475A1 (en) | 2004-01-19 |
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