NO322800B1 - Heterocykliske sulfonamider, farmasoytiske preparater omfattende slike, anvendelse av disse for fremstilling av medikamenter for behandling eller forebygging av lidelser, fremstilling av disse samt anvendelse av disse for behandling av sykdommer. - Google Patents
Heterocykliske sulfonamider, farmasoytiske preparater omfattende slike, anvendelse av disse for fremstilling av medikamenter for behandling eller forebygging av lidelser, fremstilling av disse samt anvendelse av disse for behandling av sykdommer. Download PDFInfo
- Publication number
- NO322800B1 NO322800B1 NO20013454A NO20013454A NO322800B1 NO 322800 B1 NO322800 B1 NO 322800B1 NO 20013454 A NO20013454 A NO 20013454A NO 20013454 A NO20013454 A NO 20013454A NO 322800 B1 NO322800 B1 NO 322800B1
- Authority
- NO
- Norway
- Prior art keywords
- methoxy
- phenoxy
- pyridine
- pyrimidin
- methyl
- Prior art date
Links
- -1 Heterocyclic sulfonamides Chemical class 0.000 title claims description 97
- 229940124530 sulfonamide Drugs 0.000 title claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000003814 drug Substances 0.000 title claims description 8
- 201000010099 disease Diseases 0.000 title claims description 5
- 230000002265 prevention Effects 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 28
- 229940079593 drug Drugs 0.000 title description 6
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 94
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 239000002904 solvent Substances 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- PWSQPYYJRFUQNY-UHFFFAOYSA-N 4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-methylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridine-2-carboxylic acid Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C(O)=O)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 PWSQPYYJRFUQNY-UHFFFAOYSA-N 0.000 claims description 26
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 150000003456 sulfonamides Chemical class 0.000 claims description 12
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- USAZCYCMURFAHN-UHFFFAOYSA-N n-[2-(3-hydroxyphenyl)-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-methylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(O)C=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 USAZCYCMURFAHN-UHFFFAOYSA-N 0.000 claims description 8
- TZGPRVZHYJHRJM-UHFFFAOYSA-N n-[2-(2-cyanopyridin-4-yl)-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-methylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C#N)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 TZGPRVZHYJHRJM-UHFFFAOYSA-N 0.000 claims description 7
- DSPWOBHBGWPXJE-UHFFFAOYSA-N 4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-propan-2-ylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridine-2-carboxylic acid Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C(O)=O)OC)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 DSPWOBHBGWPXJE-UHFFFAOYSA-N 0.000 claims description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- HWDVVFJLGKKDDY-UHFFFAOYSA-N n-[2-[2-(hydroxymethyl)pyridin-4-yl]-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-methylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(CO)N=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 HWDVVFJLGKKDDY-UHFFFAOYSA-N 0.000 claims description 6
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 5
- 230000002159 abnormal effect Effects 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 230000008694 endothelial dysfunction Effects 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- JBMOXASJKXMRQK-UHFFFAOYSA-N methyl 4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-methylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC(C=2N=C(OC)C(OC=3C(=CC=CC=3)OC)=C(NS(=O)(=O)C=3N=CC(C)=CC=3)N=2)=C1 JBMOXASJKXMRQK-UHFFFAOYSA-N 0.000 claims description 5
- MGOPRDLMTJAUDR-UHFFFAOYSA-N n-[2-[3-(2-hydroxyethoxy)phenyl]-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-methylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(OCCO)C=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 MGOPRDLMTJAUDR-UHFFFAOYSA-N 0.000 claims description 5
- IPCRQNKALGQPEY-UHFFFAOYSA-N n-[6-methoxy-5-(2-methoxyphenoxy)-2-[2-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-4-yl]pyrimidin-4-yl]-5-methylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2N=C(C)ON=2)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 IPCRQNKALGQPEY-UHFFFAOYSA-N 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 230000006442 vascular tone Effects 0.000 claims description 5
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- JBOAZACHEBUCCG-UHFFFAOYSA-N ethyl 4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-methylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C=2N=C(OC)C(OC=3C(=CC=CC=3)OC)=C(NS(=O)(=O)C=3N=CC(C)=CC=3)N=2)=C1 JBOAZACHEBUCCG-UHFFFAOYSA-N 0.000 claims description 4
- FFIICJXAEMQRPV-UHFFFAOYSA-N ethyl 4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-propan-2-ylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C=2N=C(OC)C(OC=3C(=CC=CC=3)OC)=C(NS(=O)(=O)C=3N=CC(=CC=3)C(C)C)N=2)=C1 FFIICJXAEMQRPV-UHFFFAOYSA-N 0.000 claims description 4
- LXNTVTQZKZHOQG-UHFFFAOYSA-N methyl 4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-propan-2-ylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC(C=2N=C(OC)C(OC=3C(=CC=CC=3)OC)=C(NS(=O)(=O)C=3N=CC(=CC=3)C(C)C)N=2)=C1 LXNTVTQZKZHOQG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 3
- JVISYACOKHFQLD-UHFFFAOYSA-N N'-hydroxy-4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-methylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridine-2-carboximidamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C(=N)NO)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 JVISYACOKHFQLD-UHFFFAOYSA-N 0.000 claims description 3
- ZDLIYCVDCFABIY-UHFFFAOYSA-N [3-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-methylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]phenyl] acetate Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(OC(C)=O)C=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 ZDLIYCVDCFABIY-UHFFFAOYSA-N 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- PTOBBLWJHXHHBN-UHFFFAOYSA-N n-[2-[2-(hydroxymethyl)pyridin-4-yl]-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-propan-2-ylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(CO)N=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 PTOBBLWJHXHHBN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- BUIBBWMIISPCPE-UHFFFAOYSA-N 4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-propan-2-ylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridine-2-carboxamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C(N)=O)OC)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 BUIBBWMIISPCPE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- LEPZHONWBRDTIQ-UHFFFAOYSA-N n-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-oxo-1h-pyridin-4-yl)pyrimidin-4-yl]-5-methylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(O)N=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 LEPZHONWBRDTIQ-UHFFFAOYSA-N 0.000 claims description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- DTVHASKEQAUBMN-UHFFFAOYSA-N N'-hydroxy-4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-propan-2-ylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridine-2-carboximidamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C(=N)NO)OC)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 DTVHASKEQAUBMN-UHFFFAOYSA-N 0.000 claims 1
- IHKAXUYWYVTCEJ-UHFFFAOYSA-N ethyl 2-[3-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-methylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(C=2N=C(OC)C(OC=3C(=CC=CC=3)OC)=C(NS(=O)(=O)C=3N=CC(C)=CC=3)N=2)=C1 IHKAXUYWYVTCEJ-UHFFFAOYSA-N 0.000 claims 1
- ILWORCFVIJMBEH-UHFFFAOYSA-N n-[2-[2-(2-hydroxyethoxy)pyridin-4-yl]-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-methyl-1,3-thiazole-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(OCCO)N=CC=2)OC)=C1NS(=O)(=O)C1=NC=C(C)S1 ILWORCFVIJMBEH-UHFFFAOYSA-N 0.000 claims 1
- IQCNZVLOUOHMKZ-UHFFFAOYSA-N n-[2-[2-(2-hydroxyethoxy)pyridin-4-yl]-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-propan-2-ylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(OCCO)N=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 IQCNZVLOUOHMKZ-UHFFFAOYSA-N 0.000 claims 1
- GBVBKQUMFUNJSX-UHFFFAOYSA-N n-[2-[2-(methanesulfonamidomethyl)pyridin-4-yl]-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-methylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(CNS(C)(=O)=O)N=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 GBVBKQUMFUNJSX-UHFFFAOYSA-N 0.000 claims 1
- WDTDILVDYHGPTR-UHFFFAOYSA-N n-[[4-[4-methoxy-5-(2-methoxyphenoxy)-6-[(5-propan-2-ylpyridin-2-yl)sulfonylamino]pyrimidin-2-yl]pyridin-2-yl]methyl]acetamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(CNC(C)=O)N=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 WDTDILVDYHGPTR-UHFFFAOYSA-N 0.000 claims 1
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- DFGSIFUHAZKRDK-UHFFFAOYSA-N potassium;5-propan-2-ylpyridine-2-sulfonamide Chemical compound [K].CC(C)C1=CC=C(S(N)(=O)=O)N=C1 DFGSIFUHAZKRDK-UHFFFAOYSA-N 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
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- Reproductive Health (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99100784 | 1999-01-18 | ||
| PCT/EP2000/000103 WO2000042035A1 (en) | 1999-01-18 | 2000-01-10 | 4-(heterocyclylsulfonamido) -5-methoxy-6- (2-methoxyphenoxy) -2-phenyl- or pyridylpyrimidines as endothelin receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20013454D0 NO20013454D0 (no) | 2001-07-12 |
| NO20013454L NO20013454L (no) | 2001-07-12 |
| NO322800B1 true NO322800B1 (no) | 2006-12-11 |
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| NO20013454A NO322800B1 (no) | 1999-01-18 | 2001-07-12 | Heterocykliske sulfonamider, farmasoytiske preparater omfattende slike, anvendelse av disse for fremstilling av medikamenter for behandling eller forebygging av lidelser, fremstilling av disse samt anvendelse av disse for behandling av sykdommer. |
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| US7517880B2 (en) * | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| US20080300281A1 (en) * | 1997-12-22 | 2008-12-04 | Jacques Dumas | Inhibition of p38 Kinase Activity Using Aryl and Heteroaryl Substituted Heterocyclic Ureas |
| US20080269265A1 (en) * | 1998-12-22 | 2008-10-30 | Scott Miller | Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas |
| US7928239B2 (en) | 1999-01-13 | 2011-04-19 | Bayer Healthcare Llc | Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas |
| ME00275B (me) * | 1999-01-13 | 2011-02-10 | Bayer Corp | ω-KARBOKSIARIL SUPSTITUISANI DIFENIL KARBAMIDI KAO INHIBITORI RAF KINAZE |
| EP1140840B1 (en) * | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| CA2359244C (en) | 1999-01-13 | 2013-10-08 | Bayer Corporation | .omega.-carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
| US6417360B1 (en) * | 1999-03-03 | 2002-07-09 | Hoffmann-La Roche Inc. | Heterocyclic sulfonamides |
| MY140724A (en) | 2000-07-21 | 2010-01-15 | Actelion Pharmaceuticals Ltd | Novel arylethene-sulfonamides |
| NZ525614A (en) * | 2000-12-18 | 2005-03-24 | Actelion Pharmaceuticals Ltd | Novel sulfamides and their use as endothelin receptor antagonists |
| US7371763B2 (en) * | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
| ES2275931T5 (es) * | 2001-12-03 | 2018-10-23 | Bayer Healthcare Llc | Compuestos de aril-urea en combinación con otros agentes citostáticos o citotóxicos para tratamiento de cánceres humanos |
| WO2003068229A1 (en) * | 2002-02-11 | 2003-08-21 | Bayer Pharmaceuticals Corporation | Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors |
| DK1478358T3 (da) | 2002-02-11 | 2013-10-07 | Bayer Healthcare Llc | Sorafenibtosylat til behandling af sygdomme kendetegnet ved unormal angiogenese |
| WO2003068746A1 (en) | 2002-02-11 | 2003-08-21 | Bayer Pharmaceuticals Corporation | Aryl ureas as kinase inhibitors |
| US20040023961A1 (en) * | 2002-02-11 | 2004-02-05 | Bayer Corporation | Aryl ureas with raf kinase and angiogenisis inhibiting activity |
| EP1569914B1 (en) * | 2002-12-02 | 2009-02-18 | Actelion Pharmaceuticals Ltd. | Pyrimidine-sulfamides and their use as endothelian receptor antagonist |
| US7269460B2 (en) * | 2003-02-28 | 2007-09-11 | Medtronic, Inc. | Method and apparatus for evaluating and optimizing ventricular synchronization |
| UY28213A1 (es) | 2003-02-28 | 2004-09-30 | Bayer Pharmaceuticals Corp | Nuevos derivados de cianopiridina útiles en el tratamiento de cáncer y otros trastornos. |
| PT1626714E (pt) | 2003-05-20 | 2007-08-24 | Bayer Pharmaceuticals Corp | Diarilureias para doenças mediadas por pdgfr |
| ES2297490T3 (es) | 2003-07-23 | 2008-05-01 | Bayer Pharmaceuticals Corporation | Omega-carboxiarildifenilurea fluoro sustituida para el tratamiento y prevencion de enfermadades y afecciones. |
| CR9465A (es) * | 2005-03-25 | 2008-06-19 | Surface Logix Inc | Compuestos mejorados farmacocineticamente |
| KR20080111137A (ko) * | 2006-04-13 | 2008-12-22 | 액테리온 파마슈티칼 리미티드 | 초기 단계 특발성 폐 섬유증을 위한 엔도텔린 수용체 대항제 |
| EP2021324B1 (en) | 2006-05-29 | 2011-12-14 | NicOx S.A. | Nitrated heterocyclic compounds as endothelin receptor antagonist |
| AR062501A1 (es) | 2006-08-29 | 2008-11-12 | Actelion Pharmaceuticals Ltd | Composiciones terapeuticas |
| MX2010001837A (es) | 2007-08-17 | 2010-03-10 | Actelion Pharmaceuticals Ltd | Derivados de 4-pirimidinasulfamida. |
| CN107108550B (zh) * | 2014-11-21 | 2020-03-03 | 大金工业株式会社 | 新型的氟代不饱和环状碳酸酯及其制造方法 |
| CN109260164A (zh) * | 2018-10-07 | 2019-01-25 | 威海贯标信息科技有限公司 | 一种阿伏生坦片剂组合物 |
| CN112898208B (zh) * | 2021-01-29 | 2023-06-20 | 中国医科大学 | 苯基嘧啶胺类抗肿瘤化合物及其制备方法和应用 |
| CN112778215B (zh) * | 2021-01-29 | 2023-06-20 | 中国医科大学 | 2-甲氧基苯氧基嘧啶类抗肿瘤化合物及其制备方法和应用 |
| EP4448511A1 (en) | 2021-12-17 | 2024-10-23 | Idorsia Pharmaceuticals Ltd | Clazosentan disodium salt, its preparation and pharmaceutical compositions comprising the same |
Family Cites Families (5)
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| CA2162630C (en) * | 1994-11-25 | 2007-05-01 | Volker Breu | Sulfonamides |
| US5837708A (en) | 1994-11-25 | 1998-11-17 | Hoffmann-La Roche Inc. | Sulphonamides |
| WO1996016963A1 (de) * | 1994-11-25 | 1996-06-06 | F. Hoffmann-La Roche Ag | Sulfonamide und deren verwendung als heilmittel |
| TW313568B (pt) * | 1994-12-20 | 1997-08-21 | Hoffmann La Roche | |
| EP0882719B1 (en) * | 1995-12-20 | 2001-05-16 | Yamanouchi Pharmaceutical Co. Ltd. | Arylethenesulfonamide derivatives and drug composition containing the same |
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