KR100445085B1 - 신규한설폰아미드 - Google Patents
신규한설폰아미드 Download PDFInfo
- Publication number
- KR100445085B1 KR100445085B1 KR1019970704135A KR19970704135A KR100445085B1 KR 100445085 B1 KR100445085 B1 KR 100445085B1 KR 1019970704135 A KR1019970704135 A KR 1019970704135A KR 19970704135 A KR19970704135 A KR 19970704135A KR 100445085 B1 KR100445085 B1 KR 100445085B1
- Authority
- KR
- South Korea
- Prior art keywords
- methoxy
- phenoxy
- pyridin
- pyrimidin
- ethoxy
- 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.)
- Expired - Lifetime
Links
- 229940124530 sulfonamide Drugs 0.000 title description 3
- 150000003456 sulfonamides Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 102000002045 Endothelin Human genes 0.000 claims abstract description 10
- 108050009340 Endothelin Proteins 0.000 claims abstract description 10
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 230000000694 effects Effects 0.000 claims abstract description 8
- 206010020772 Hypertension Diseases 0.000 claims abstract description 4
- -1 cyano, carboxy Chemical class 0.000 claims description 362
- 238000000034 method Methods 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- HXAZFIXWZPERHB-UHFFFAOYSA-N 5-propan-2-ylpyridine-2-sulfonic acid Chemical compound CC(C)C1=CC=C(S(O)(=O)=O)N=C1 HXAZFIXWZPERHB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
- XYDHSCZUHCZWHJ-UHFFFAOYSA-N 5-methylpyridine-2-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)N=C1 XYDHSCZUHCZWHJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- WOZCSRYOBKSMBL-UHFFFAOYSA-N 1,3-benzodioxole-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2OCOC2=C1 WOZCSRYOBKSMBL-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 150000001540 azides Chemical class 0.000 claims description 4
- HDEQVSSOIDIBRF-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(N=CC=2)C=2NN=NN=2)=NC(OCCO)=C1OC1=CC=CC=C1OC HDEQVSSOIDIBRF-UHFFFAOYSA-N 0.000 claims description 4
- UKDSUPWSXLYLQP-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-4-methylbenzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C)C=C1 UKDSUPWSXLYLQP-UHFFFAOYSA-N 0.000 claims description 4
- HPMMXOJNBRQSRV-UHFFFAOYSA-N 4-tert-butyl-n-[5-(2-chloro-5-methoxyphenoxy)-6-(2-hydroxyethoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=C(Cl)C(OC=2C(=NC(=NC=2NS(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)C=2C=C(N=CC=2)C=2NN=NN=2)OCCO)=C1 HPMMXOJNBRQSRV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 125000000815 N-oxide group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001411 amidrazones Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- UMIYJHCDVVUVTQ-UHFFFAOYSA-N n-[2-(2-cyanopyridin-4-yl)-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]-2,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C(=C(OCCO)N=C(N=2)C=2C=C(N=CC=2)C#N)OC=2C(=CC=CC=2)OC)=C1 UMIYJHCDVVUVTQ-UHFFFAOYSA-N 0.000 claims description 3
- GYZKCMRPFJRTKQ-UHFFFAOYSA-N n-[2-(2-cyanopyridin-4-yl)-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(N=CC=2)C#N)=NC(OCCO)=C1OC1=CC=CC=C1OC GYZKCMRPFJRTKQ-UHFFFAOYSA-N 0.000 claims description 3
- FNMAQJQQWOBFAW-UHFFFAOYSA-N n-[2-(2-cyanopyridin-4-yl)-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]-4-methylbenzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C#N)OCCO)=C1NS(=O)(=O)C1=CC=C(C)C=C1 FNMAQJQQWOBFAW-UHFFFAOYSA-N 0.000 claims description 3
- IFDFZXKDKJLNSU-UHFFFAOYSA-N n-[2-(2-cyanopyridin-4-yl)-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C#N)OCCO)=C1NS(=O)(=O)C1=CC=CC=C1 IFDFZXKDKJLNSU-UHFFFAOYSA-N 0.000 claims description 3
- ZBNTWRRRSSLODB-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-2,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C(=C(OCCO)N=C(N=2)C=2C=C(N=CC=2)C=2NN=NN=2)OC=2C(=CC=CC=2)OC)=C1 ZBNTWRRRSSLODB-UHFFFAOYSA-N 0.000 claims description 3
- NZBHBMWOKBFMAW-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(N=CC=2)C=2NN=NN=2)=NC(OCCO)=C1OC1=CC=CC=C1OC NZBHBMWOKBFMAW-UHFFFAOYSA-N 0.000 claims description 3
- XNMPTHORQNNFIE-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-4-methylsulfanylbenzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(SC)C=C1 XNMPTHORQNNFIE-UHFFFAOYSA-N 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- JIBMEFUIGPATLZ-UHFFFAOYSA-N 1,3-benzodioxole-4-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C1OCO2 JIBMEFUIGPATLZ-UHFFFAOYSA-N 0.000 claims description 2
- ZPRLVZPTIWUEGY-UHFFFAOYSA-N 2-[5-(2-methoxyphenoxy)-6-(pyridin-3-ylsulfonylamino)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]oxyethyl n-pyridin-2-ylcarbamate Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C2=NNN=N2)OCCOC(=O)NC=2N=CC=CC=2)=C1NS(=O)(=O)C1=CC=CN=C1 ZPRLVZPTIWUEGY-UHFFFAOYSA-N 0.000 claims description 2
- FYOQAYNXPKBFJL-UHFFFAOYSA-N 2-[5-(2-methoxyphenoxy)-6-[(5-methylpyridin-2-yl)sulfonylamino]-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]oxyethyl n-pyridin-2-ylcarbamate Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCOC(=O)NC=2N=CC=CC=2)=C1NS(=O)(=O)C1=CC=C(C)C=N1 FYOQAYNXPKBFJL-UHFFFAOYSA-N 0.000 claims description 2
- AIXICGRFFMJBAC-UHFFFAOYSA-N 2-[6-[(4-tert-butylphenyl)sulfonylamino]-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)-1h-pyridin-2-yl]pyrimidin-4-yl]oxyethyl n-pyridin-2-ylcarbamate Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C2(C=CC=CN2)C=2NN=NN=2)OCCOC(=O)NC=2N=CC=CC=2)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 AIXICGRFFMJBAC-UHFFFAOYSA-N 0.000 claims description 2
- WAZRBGCDCZBPNI-UHFFFAOYSA-N 4-tert-butyl-n-[2-(2-cyanopyridin-4-yl)-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C#N)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 WAZRBGCDCZBPNI-UHFFFAOYSA-N 0.000 claims description 2
- DQWVRLQQDDEQAS-UHFFFAOYSA-N 4-tert-butyl-n-[2-(3-cyanophenyl)-5-(2-methoxyphenoxy)-6-(2-phenylmethoxyethoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(C=CC=2)C#N)OCCOCC=2C=CC=CC=2)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 DQWVRLQQDDEQAS-UHFFFAOYSA-N 0.000 claims description 2
- WEUUDVAKLXYINL-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(1-oxidopyridin-1-ium-4-yl)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C[N+]([O-])=CC=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 WEUUDVAKLXYINL-UHFFFAOYSA-N 0.000 claims description 2
- NJXRDIFLORYXNI-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 NJXRDIFLORYXNI-UHFFFAOYSA-N 0.000 claims description 2
- ICLRVCISJHBKTN-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[3-(2h-tetrazol-5-yl)phenyl]pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(C=CC=2)C=2NN=NN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 ICLRVCISJHBKTN-UHFFFAOYSA-N 0.000 claims description 2
- UEBSLFMBCOAFNZ-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[4-(2h-tetrazol-5-yl)phenyl]pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=CC(=CC=2)C=2NN=NN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 UEBSLFMBCOAFNZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 206010047163 Vasospasm Diseases 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- NLPBOPFGLGUZMN-UHFFFAOYSA-N n-[2-(2-cyanopyridin-4-yl)-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(N=CC=2)C#N)=NC(OCCO)=C1OC1=CC=CC=C1OC NLPBOPFGLGUZMN-UHFFFAOYSA-N 0.000 claims description 2
- ZTWJEDKVMNINTP-UHFFFAOYSA-N n-[2-(2-cyanopyridin-4-yl)-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]-4-methylsulfanylbenzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C#N)OCCO)=C1NS(=O)(=O)C1=CC=C(SC)C=C1 ZTWJEDKVMNINTP-UHFFFAOYSA-N 0.000 claims description 2
- ORSUOOCBOGMNKA-UHFFFAOYSA-N n-[5-(2-chloro-5-methoxyphenoxy)-6-(2-hydroxyethoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-5-propan-2-ylpyridine-2-sulfonamide Chemical compound COC1=CC=C(Cl)C(OC=2C(=NC(=NC=2NS(=O)(=O)C=2N=CC(=CC=2)C(C)C)C=2C=C(N=CC=2)C=2NN=NN=2)OCCO)=C1 ORSUOOCBOGMNKA-UHFFFAOYSA-N 0.000 claims description 2
- LFWCJABOXHSRGC-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-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)C2=NNN=N2)OCCO)=C1NS(=O)(=O)C1=CC=C(C)C=N1 LFWCJABOXHSRGC-UHFFFAOYSA-N 0.000 claims description 2
- QINSBYCECDCCDT-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCO)=C1NS(=O)(=O)C1=CC=CC=C1 QINSBYCECDCCDT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- UTIPCUGALUKVRH-UHFFFAOYSA-N 2-[5-(2-methoxyphenoxy)-6-(pyridin-3-ylsulfonylamino)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]oxyethyl n-(1,3-benzodioxol-5-yl)carbamate Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCOC(=O)NC=2C=C3OCOC3=CC=2)=C1NS(=O)(=O)C1=CC=CN=C1 UTIPCUGALUKVRH-UHFFFAOYSA-N 0.000 claims 1
- BDETYSXRVPDGND-UHFFFAOYSA-N 2-[5-(2-methoxyphenoxy)-6-[(4-methoxyphenyl)sulfonylamino]-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]oxyethyl n-(1,3-benzodioxol-5-yl)carbamate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(N=CC=2)C=2NN=NN=2)=NC(OCCOC(=O)NC=2C=C3OCOC3=CC=2)=C1OC1=CC=CC=C1OC BDETYSXRVPDGND-UHFFFAOYSA-N 0.000 claims 1
- NYSKZEYYOVJLQL-UHFFFAOYSA-N 2-[5-(2-methoxyphenoxy)-6-[(4-methylsulfanylphenyl)sulfonylamino]-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]oxyethyl n-pyridin-2-ylcarbamate Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCOC(=O)NC=2N=CC=CC=2)=C1NS(=O)(=O)C1=CC=C(SC)C=C1 NYSKZEYYOVJLQL-UHFFFAOYSA-N 0.000 claims 1
- MIOKUIIVWRZYHA-UHFFFAOYSA-N 2-[5-(2-methoxyphenoxy)-6-[(5-propan-2-ylpyridin-2-yl)sulfonylamino]-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]oxyethyl n-(1,3-benzodioxol-5-yl)carbamate Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCOC(=O)NC=2C=C3OCOC3=CC=2)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 MIOKUIIVWRZYHA-UHFFFAOYSA-N 0.000 claims 1
- ISGDRCXXQVSZHP-UHFFFAOYSA-N 2-[5-(2-methoxyphenoxy)-6-[(5-propan-2-ylpyridin-2-yl)sulfonylamino]-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]oxyethyl n-pyridin-2-ylcarbamate Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCOC(=O)NC=2N=CC=CC=2)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 ISGDRCXXQVSZHP-UHFFFAOYSA-N 0.000 claims 1
- XEUQIBDUWHMESF-UHFFFAOYSA-N 2-[6-(1,3-benzodioxol-5-ylsulfonylamino)-5-(2-chloro-5-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]oxyethyl n-pyridin-2-ylcarbamate Chemical compound COC1=CC=C(Cl)C(OC=2C(=NC(=NC=2NS(=O)(=O)C=2C=C3OCOC3=CC=2)C=2C=C(N=CC=2)C=2NN=NN=2)OCCOC(=O)NC=2N=CC=CC=2)=C1 XEUQIBDUWHMESF-UHFFFAOYSA-N 0.000 claims 1
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- NEGHGTZIQCZFBE-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]pyridine-3-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C=2NN=NN=2)OCCO)=C1NS(=O)(=O)C1=CC=CN=C1 NEGHGTZIQCZFBE-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VUENSYJCBOSTCS-UHFFFAOYSA-N tert-butyl-imidazol-1-yl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)N1C=CN=C1 VUENSYJCBOSTCS-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000011706 wistar kyoto rat Methods 0.000 description 1
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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D403/02—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
- C07D403/10—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 carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Bipolar Transistors (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Steroid Compounds (AREA)
- Surgical Instruments (AREA)
- Lubricants (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH383794 | 1994-12-20 | ||
| CH3837/94-6 | 1994-12-20 | ||
| CH241995 | 1995-08-24 | ||
| CH2419/95-1 | 1995-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR100445085B1 true KR100445085B1 (ko) | 2004-10-14 |
Family
ID=25690401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019970704135A Expired - Lifetime KR100445085B1 (ko) | 1994-12-20 | 1995-12-08 | 신규한설폰아미드 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6004965A (https=) |
| EP (1) | EP0799209B1 (https=) |
| JP (1) | JP2989014B2 (https=) |
| KR (1) | KR100445085B1 (https=) |
| CN (1) | CN1098254C (https=) |
| AT (1) | ATE246681T1 (https=) |
| AU (1) | AU701767B2 (https=) |
| BR (1) | BR9510104A (https=) |
| CA (1) | CA2208018C (https=) |
| CY (1) | CY2495B1 (https=) |
| CZ (1) | CZ287916B6 (https=) |
| DE (1) | DE69531457T2 (https=) |
| DK (1) | DK0799209T3 (https=) |
| ES (1) | ES2203649T3 (https=) |
| FI (1) | FI120397B (https=) |
| HU (1) | HU228619B1 (https=) |
| IL (1) | IL116385A (https=) |
| MA (1) | MA23744A1 (https=) |
| MY (1) | MY131126A (https=) |
| NO (1) | NO316645B1 (https=) |
| NZ (1) | NZ297797A (https=) |
| PT (1) | PT799209E (https=) |
| SA (1) | SA95160421B1 (https=) |
| TW (1) | TW313568B (https=) |
| WO (1) | WO1996019459A1 (https=) |
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| US6063911A (en) * | 1993-12-01 | 2000-05-16 | Marine Polymer Technologies, Inc. | Methods and compositions for treatment of cell proliferative disorders |
| TW555765B (en) | 1996-07-09 | 2003-10-01 | Amgen Inc | Low molecular weight soluble tumor necrosis factor type-I and type-II proteins |
| ES2312179T3 (es) | 1996-12-06 | 2009-02-16 | Amgen Inc. | Terapia combinada que utiliza un inhibidor del il-1 para el tratamiento de enfermedades mediadas por el il-1. |
| DK0897914T3 (da) * | 1997-08-19 | 2004-09-27 | Hoffmann La Roche | Fremgangsmåde til fremstilling af 2,5-disubstituerede pyridiner |
| US7329670B1 (en) | 1997-12-22 | 2008-02-12 | Bayer Pharmaceuticals Corporation | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
| US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| DK0979822T3 (da) * | 1998-08-10 | 2006-03-27 | Hoffmann La Roche | Fremgangsmåde til fremstilling af 2-carbamoyl-pyridiner |
| US6660843B1 (en) | 1998-10-23 | 2003-12-09 | Amgen Inc. | Modified peptides as therapeutic agents |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| ME00275B (me) | 1999-01-13 | 2011-02-10 | Bayer Corp | ω-KARBOKSIARIL SUPSTITUISANI DIFENIL KARBAMIDI KAO INHIBITORI RAF KINAZE |
| US7928239B2 (en) | 1999-01-13 | 2011-04-19 | Bayer Healthcare Llc | Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas |
| EP1158985B1 (en) | 1999-01-13 | 2011-12-28 | Bayer HealthCare LLC | OMEGA-CARBOXY ARYL SUBSTITUTED DIPHENYL UREAS AS p38 KINASE INHIBITORS |
| EP1140840B1 (en) * | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| TWI284642B (en) * | 1999-01-18 | 2007-08-01 | Hoffmann La Roche | Novel heterocyclic sulfonamides |
| US6417360B1 (en) * | 1999-03-03 | 2002-07-09 | Hoffmann-La Roche Inc. | Heterocyclic sulfonamides |
| AU747596B2 (en) * | 1999-05-22 | 2002-05-16 | Actelion Pharmaceuticals Ltd | Aqueous pharmaceutical composition |
| ZA200002318B (en) * | 1999-05-22 | 2000-11-16 | Actelion Pharmaceuticals Ltd | Aqueous pharmaceutical composition. |
| CA2315614C (en) | 1999-07-29 | 2004-11-02 | Pfizer Inc. | Pyrazoles |
| EP1137642B1 (en) | 1999-09-03 | 2007-12-05 | Actelion Pharmaceuticals Ltd. | Bis-sulfonamides |
| JP2003518102A (ja) * | 1999-12-22 | 2003-06-03 | アクテリオン ファマシューティカルズ リミテッド | ブチンジオール誘導体 |
| WO2001081338A1 (en) * | 2000-04-25 | 2001-11-01 | Actelion Pharmaceuticals Ltd | Substituted sulfonylaminopyrimidines |
| US6387915B2 (en) | 2000-05-31 | 2002-05-14 | Pfizer Inc. | Isoxazole-sulfonamide endothelin antagonists |
| US6670362B2 (en) | 2000-09-20 | 2003-12-30 | Pfizer Inc. | Pyridazine endothelin antagonists |
| US8168616B1 (en) | 2000-11-17 | 2012-05-01 | Novartis Ag | Combination comprising a renin inhibitor and an angiotensin receptor inhibitor for hypertension |
| AU2002227984B8 (en) * | 2000-12-18 | 2007-01-04 | Actelion Pharmaceuticals Ltd. | Novel sulfamides and their use as endothelin receptor antagonists |
| US7235576B1 (en) | 2001-01-12 | 2007-06-26 | Bayer Pharmaceuticals Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| WO2002083650A1 (en) * | 2001-04-11 | 2002-10-24 | Actelion Pharmaceuticals Ltd | Novel sulfonylamino-pyrimidines |
| US7371763B2 (en) | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
| ATE529406T1 (de) | 2002-02-11 | 2011-11-15 | Bayer Healthcare Llc | Aryl-harnstoffe als kinase inhibitoren |
| WO2003068229A1 (en) | 2002-02-11 | 2003-08-21 | Bayer Pharmaceuticals Corporation | Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors |
| SI1478358T1 (sl) | 2002-02-11 | 2013-09-30 | Bayer Healthcare Llc | Sorafenib tozilat za zdravljenje bolezni, značilnih po abnormalni angiogenezi |
| US20040002451A1 (en) | 2002-06-20 | 2004-01-01 | Bruce Kerwin | Compositions of pegylated soluble tumor necrosis factor receptors and methods of preparing |
| CA2507334C (en) | 2002-12-02 | 2013-05-07 | Actelion Pharmaceuticals Ltd. | Pyrimidine-sulfamides and their use as endothelian receptor antagonist |
| US7557129B2 (en) | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
| EP1636585B2 (en) | 2003-05-20 | 2012-06-13 | Bayer HealthCare LLC | Diaryl ureas with kinase inhibiting activity |
| EP1663978B1 (en) | 2003-07-23 | 2007-11-28 | Bayer Pharmaceuticals Corporation | Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions |
| GB0327839D0 (en) | 2003-12-01 | 2003-12-31 | Novartis Ag | Organic compounds |
| NZ549535A (en) | 2004-03-17 | 2010-11-26 | Novartis Ag | Use of aliskiren for treating renal and other disorders |
| TW200628467A (en) | 2004-11-11 | 2006-08-16 | Actelion Pharmaceuticals Ltd | Novel sulfamides |
| US7402730B1 (en) | 2005-02-03 | 2008-07-22 | Lexicon Pharmaceuticals, Inc. | Knockout animals manifesting hyperlipidemia |
| GT200600381A (es) | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
| EP2049517B1 (en) | 2006-07-20 | 2013-11-27 | Novartis AG | Amino-piperidine derivatives as cetp inhibitors |
| AR062501A1 (es) | 2006-08-29 | 2008-11-12 | Actelion Pharmaceuticals Ltd | Composiciones terapeuticas |
| WO2008073300A2 (en) | 2006-12-08 | 2008-06-19 | Lexicon Pharmaceuticals, Inc. | Monoclonal antibodies against angptl3 |
| AU2008219065B2 (en) | 2007-02-19 | 2014-01-30 | Marine Polymer Technologies, Inc. | Hemostatic compositions and therapeutic regimens |
| MX2010001837A (es) | 2007-08-17 | 2010-03-10 | Actelion Pharmaceuticals Ltd | Derivados de 4-pirimidinasulfamida. |
| FR2921062A1 (fr) * | 2007-09-17 | 2009-03-20 | Commissariat Energie Atomique | Composes utiles comme ligands et notamment comme chromophores organiques de complexation des lanthanides et leurs applications |
| CN101910150B (zh) | 2007-11-05 | 2013-09-18 | 诺瓦提斯公司 | 作为cetp抑制剂、可用于治疗疾病如高脂血症或动脉硬化的4-苄基氨基-1-羧基酰基哌啶衍生物 |
| MX2010006063A (es) | 2007-12-03 | 2010-07-01 | Novartis Ag | Derivados de 4-bencil-amino-pirrolidina 1,2-disustituida como inhibidores de la proteina de transferencia de colesteril-ester (cetp) utiles para el tratamiento de las enfermedades tales como hiperlipidemia o arterioesclerosis. |
| US8455522B2 (en) | 2009-05-15 | 2013-06-04 | Novartis Ag | Benzoxazolone derivatives as aldosterone synthase inhibitors |
| NZ596302A (en) | 2009-05-15 | 2014-01-31 | Novartis Ag | Aryl pyridine as aldosterone synthase inhibitors |
| JP5466759B2 (ja) | 2009-05-28 | 2014-04-09 | ノバルティス アーゲー | ネプリライシン阻害剤としての置換アミノ酪酸誘導体 |
| SG176009A1 (en) | 2009-05-28 | 2011-12-29 | Novartis Ag | Substituted aminopropionic derivatives as neprilysin inhibitors |
| US8519134B2 (en) | 2009-11-17 | 2013-08-27 | Novartis Ag | Aryl-pyridine derivatives as aldosterone synthase inhibitors |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| ES2472446T3 (es) | 2009-11-30 | 2014-07-01 | Novartis Ag | Derivados de imidazol como inhibidores de aldosterona sintasa |
| BR112012025844A2 (pt) | 2010-04-15 | 2017-07-18 | Marine Polymer Tech Inc | uso de nanofibras snag |
| US8673974B2 (en) | 2010-11-16 | 2014-03-18 | Novartis Ag | Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors |
| US8877815B2 (en) | 2010-11-16 | 2014-11-04 | Novartis Ag | Substituted carbamoylcycloalkyl acetic acid derivatives as NEP |
| JP6033229B2 (ja) | 2010-11-24 | 2016-11-30 | レクシコン ファーマシューティカルズ インコーポレイテッド | Ｎｏｔｕｍペクチンアセチルエステラーゼと結合する抗体 |
| CA2832859C (en) | 2011-04-15 | 2020-06-16 | Marine Polymer Technologies, Inc. | Treatment of disease with poly-n-acetylglucosamine nanofibers |
| UY35144A (es) | 2012-11-20 | 2014-06-30 | Novartis Ag | Miméticos lineales sintéticos de apelina para el tratamiento de insuficiencia cardiaca |
| US9383357B2 (en) | 2012-12-07 | 2016-07-05 | Northwestern University | Biomarker for replicative senescence |
| TR201808541T4 (tr) | 2013-02-14 | 2018-07-23 | Novartis Ag | Nep (nötr endopeptidaz) inhibitörleri olarak ikame edilmiş bisfenil butanoik fosfonik asit türevleri. |
| KR20160031551A (ko) | 2013-07-25 | 2016-03-22 | 노파르티스 아게 | 심부전의 치료를 위한 시클릭 폴리펩티드 |
| HK1218252A1 (zh) | 2013-07-25 | 2017-02-10 | Novartis Ag | 合成apelin多肽之生物结合物 |
| MA41580A (fr) | 2015-01-23 | 2017-11-29 | Novartis Ag | Conjugués d'acides gras de l'apeline synthétique présentant une demi-vie améliorée |
| UY38072A (es) | 2018-02-07 | 2019-10-01 | Novartis Ag | Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos |
| TWI835843B (zh) | 2018-10-03 | 2024-03-21 | 瑞士商亨斯邁紡織染化（瑞士）有限公司 | 新的經吡啶及經嘧啶取代之三ｕｖ吸收劑 |
| CA3197265A1 (en) * | 2020-11-05 | 2022-05-12 | Timo Rager | A stable crystalline hydrate of clazosentan disodium salt |
| JP7820522B2 (ja) * | 2021-12-17 | 2026-02-25 | ネクセラファーマ株式会社 | クラゾセンタン二ナトリウム塩、その製造及びそれを含有する医薬組成物 |
| US20250228835A1 (en) * | 2024-01-12 | 2025-07-17 | Rectify Pharmaceuticals, Inc. | Pyridinyloxypyridines and related compounds and their use in treating medical conditions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW270116B (https=) * | 1991-04-25 | 1996-02-11 | Hoffmann La Roche | |
| RU2086544C1 (ru) * | 1991-06-13 | 1997-08-10 | Хоффманн-Ля Рош АГ | Бензолсульфонамидные производные пиримидина или их соли, фармацевтическая композиция для лечения заболеваний, связанных с активностью эндотелина |
| TW287160B (https=) * | 1992-12-10 | 1996-10-01 | Hoffmann La Roche | |
| TW394761B (en) * | 1993-06-28 | 2000-06-21 | Hoffmann La Roche | Novel Sulfonylamino Pyrimidines |
| IL111959A (en) * | 1993-12-17 | 2000-07-16 | Tanabe Seiyaku Co | N-(polysubstituted pyrimidin-4-yl) benzenesulfonamide derivatives their preparation and pharmaceutical compositions containing them |
-
1995
- 1995-11-11 TW TW084111957A patent/TW313568B/zh not_active IP Right Cessation
- 1995-11-29 SA SA95160421A patent/SA95160421B1/ar unknown
- 1995-12-08 HU HU9702407A patent/HU228619B1/hu unknown
- 1995-12-08 PT PT95941706T patent/PT799209E/pt unknown
- 1995-12-08 KR KR1019970704135A patent/KR100445085B1/ko not_active Expired - Lifetime
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