NO324952B1 - Nye sulfonamider, fremstilling av disse, farmasoytiske preparater inneholdende slike,anvendelse av disse forbindelsene som medikament samt anvendelse av disse for fremstilling av medikament for behandling av lidelser. - Google Patents
Nye sulfonamider, fremstilling av disse, farmasoytiske preparater inneholdende slike,anvendelse av disse forbindelsene som medikament samt anvendelse av disse for fremstilling av medikament for behandling av lidelser. Download PDFInfo
- Publication number
- NO324952B1 NO324952B1 NO20032699A NO20032699A NO324952B1 NO 324952 B1 NO324952 B1 NO 324952B1 NO 20032699 A NO20032699 A NO 20032699A NO 20032699 A NO20032699 A NO 20032699A NO 324952 B1 NO324952 B1 NO 324952B1
- Authority
- NO
- Norway
- Prior art keywords
- pyrimidin
- amide
- ethoxy
- acid
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 97
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 16
- 208000035475 disorder Diseases 0.000 title claims description 11
- 239000003814 drug Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 229940124530 sulfonamide Drugs 0.000 title description 2
- 150000003456 sulfonamides Chemical class 0.000 title description 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- -1 tri-substituted phenyl Chemical group 0.000 claims description 28
- 108050009340 Endothelin Proteins 0.000 claims description 24
- 102000002045 Endothelin Human genes 0.000 claims description 24
- 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 description 22
- 125000003118 aryl group 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
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
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- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
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- 201000011510 cancer Diseases 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- PIJUSICWAKBTEZ-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-n-(ethylsulfamoyl)pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCC)=NC=NC=1OCCOC1=NC=C(Br)C=N1 PIJUSICWAKBTEZ-UHFFFAOYSA-N 0.000 claims description 3
- GADXZXTXFHEOKH-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(ethylsulfamoyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCC)=NC=NC=1OCCOC1=NC=C(SC)C=N1 GADXZXTXFHEOKH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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- CDYRIYSNNRFTJE-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-6-[[furan-2-yl(methyl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Cl)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CO1 CDYRIYSNNRFTJE-UHFFFAOYSA-N 0.000 claims description 2
- BTENFENCPKOZJD-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[furan-2-yl(methyl)sulfamoyl]amino]-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidine Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)N(C)C1=CC=CO1 BTENFENCPKOZJD-UHFFFAOYSA-N 0.000 claims description 2
- FWIARXJRYJCABB-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(ethylsulfamoyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound C=1C=C(Cl)C=CC=1C=1C(NS(=O)(=O)NCC)=NC=NC=1OCCOC1=NC=C(SC)C=N1 FWIARXJRYJCABB-UHFFFAOYSA-N 0.000 claims description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- FGHFFSIBBSXJRS-UHFFFAOYSA-N COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)NCC1CC1 Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)NCC1CC1 FGHFFSIBBSXJRS-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- DUVSYCWKGNRJEW-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C(=NC=NC1OCCOC1=NC=C(C=N1)OC)NS(NCC1CC1)(=O)=O Chemical compound ClC1=CC=C(C=C1)C=1C(=NC=NC1OCCOC1=NC=C(C=N1)OC)NS(NCC1CC1)(=O)=O DUVSYCWKGNRJEW-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 206010047163 Vasospasm Diseases 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- VIQIKJNRAFJKTQ-UHFFFAOYSA-N n-(benzylsulfamoyl)-5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound C1=CC(Br)=CC=C1C(C(=NC=N1)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)NCC1=CC=CC=C1 VIQIKJNRAFJKTQ-UHFFFAOYSA-N 0.000 claims description 2
- XAQFWGGNTGMNHM-UHFFFAOYSA-N n-(benzylsulfamoyl)-5-(4-bromophenyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)NCC=2C=CC=CC=2)=C1C1=CC=C(Br)C=C1 XAQFWGGNTGMNHM-UHFFFAOYSA-N 0.000 claims description 2
- ADKWUFCPMCLUKI-UHFFFAOYSA-N n-(benzylsulfamoyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-chloro-5-methoxyphenoxy)pyrimidin-4-amine Chemical compound COC1=CC=C(Cl)C(OC=2C(=NC=NC=2NS(=O)(=O)NCC=2C=CC=CC=2)OCCOC=2N=CC(Br)=CN=2)=C1 ADKWUFCPMCLUKI-UHFFFAOYSA-N 0.000 claims description 2
- MNRPBSOBVCAVNX-UHFFFAOYSA-N n-(benzylsulfamoyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-amine Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)NCC1=CC=CC=C1 MNRPBSOBVCAVNX-UHFFFAOYSA-N 0.000 claims description 2
- LSQXFROVPNDBMN-UHFFFAOYSA-N n-(benzylsulfamoyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-methoxyphenoxy)pyrimidin-4-amine Chemical compound COC1=CC=CC=C1OC(C(=NC=N1)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)NCC1=CC=CC=C1 LSQXFROVPNDBMN-UHFFFAOYSA-N 0.000 claims description 2
- GMJUQVMLYSQKNY-UHFFFAOYSA-N n-(benzylsulfamoyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-2-pyridin-4-ylpyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C(C(=NC(=N1)C=2C=CN=CC=2)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)NCC1=CC=CC=C1 GMJUQVMLYSQKNY-UHFFFAOYSA-N 0.000 claims description 2
- LPHFZTKFROHBTL-UHFFFAOYSA-N n-(benzylsulfamoyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-methylphenyl)-2-pyridin-4-ylpyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C(C(=NC(=N1)C=2C=CN=CC=2)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)NCC1=CC=CC=C1 LPHFZTKFROHBTL-UHFFFAOYSA-N 0.000 claims description 2
- 230000002062 proliferating effect Effects 0.000 claims description 2
- OUCYWJAACMAXQD-UHFFFAOYSA-N pyridin-2-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=N1 OUCYWJAACMAXQD-UHFFFAOYSA-N 0.000 claims description 2
- AIOGYCKREZXJJZ-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-6-[[methyl(pyridin-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Cl)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CC=N1 AIOGYCKREZXJJZ-UHFFFAOYSA-N 0.000 claims 2
- WDQPEDYBKDHJLW-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-6-[[methyl(pyridin-3-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Cl)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CN=C1 WDQPEDYBKDHJLW-UHFFFAOYSA-N 0.000 claims 1
- DCNYMZHJYGMUAP-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-6-[[methyl(thiophen-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Cl)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CS1 DCNYMZHJYGMUAP-UHFFFAOYSA-N 0.000 claims 1
- LGFUPYWNJPMKKF-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[furan-2-yl(methyl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CO1 LGFUPYWNJPMKKF-UHFFFAOYSA-N 0.000 claims 1
- HQTCWMOCUPICJI-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CC=N1 HQTCWMOCUPICJI-UHFFFAOYSA-N 0.000 claims 1
- ISJQPCOMTBDAMT-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-3-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CN=C1 ISJQPCOMTBDAMT-UHFFFAOYSA-N 0.000 claims 1
- OHDJBKMKVMFQIY-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-4-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=NC=C1 OHDJBKMKVMFQIY-UHFFFAOYSA-N 0.000 claims 1
- ZLDJCOJFGRLYDN-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[methyl(thiophen-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CS1 ZLDJCOJFGRLYDN-UHFFFAOYSA-N 0.000 claims 1
- GWOUVHUMXSOJQE-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2N=CC=CC=2)=C1C1=CC=C(Br)C=C1 GWOUVHUMXSOJQE-UHFFFAOYSA-N 0.000 claims 1
- DKWDMCCNUCWCKU-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-4-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2C=CN=CC=2)=C1C1=CC=C(Br)C=C1 DKWDMCCNUCWCKU-UHFFFAOYSA-N 0.000 claims 1
- GRMNNBBUDDGUJW-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-6-[[methyl(thiophen-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2SC=CC=2)=C1C1=CC=C(Br)C=C1 GRMNNBBUDDGUJW-UHFFFAOYSA-N 0.000 claims 1
- MIZAELWUKAHOEP-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]-6-[[methyl(thiophen-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2SC=CC=2)=C1C1=CC=C(Br)C=C1 MIZAELWUKAHOEP-UHFFFAOYSA-N 0.000 claims 1
- SCCMBDIZRNGJIJ-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[[furan-2-yl(methyl)sulfamoyl]amino]-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2OC=CC=2)=C1C1=CC=C(Br)C=C1 SCCMBDIZRNGJIJ-UHFFFAOYSA-N 0.000 claims 1
- XYCFQJYVDREZPE-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[[furan-2-yl(methyl)sulfamoyl]amino]-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2OC=CC=2)=C1C1=CC=C(Br)C=C1 XYCFQJYVDREZPE-UHFFFAOYSA-N 0.000 claims 1
- HVSRHDAIPVEISZ-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[[methyl(pyridin-2-yl)sulfamoyl]amino]-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2N=CC=CC=2)=C1C1=CC=C(Br)C=C1 HVSRHDAIPVEISZ-UHFFFAOYSA-N 0.000 claims 1
- WTEIMXRBTNAONF-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[[methyl(pyridin-3-yl)sulfamoyl]amino]-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2C=NC=CC=2)=C1C1=CC=C(Br)C=C1 WTEIMXRBTNAONF-UHFFFAOYSA-N 0.000 claims 1
- BHPAWJNRRKCLGK-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[[methyl(pyridin-4-yl)sulfamoyl]amino]-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2C=CN=CC=2)=C1C1=CC=C(Br)C=C1 BHPAWJNRRKCLGK-UHFFFAOYSA-N 0.000 claims 1
- FAYAMAAFPRXGJT-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-n-(butylsulfamoyl)pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCCC)=NC=NC=1OCCOC1=NC=C(Br)C=N1 FAYAMAAFPRXGJT-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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EP0012890 | 2000-12-18 | ||
PCT/EP2001/014182 WO2002053557A1 (en) | 2000-12-18 | 2001-12-04 | Novel sulfamides and their use as endothelin receptor antagonists |
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NO20032699L NO20032699L (no) | 2003-06-13 |
NO20032699D0 NO20032699D0 (no) | 2003-06-13 |
NO324952B1 true NO324952B1 (no) | 2008-01-14 |
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NO20032699A NO324952B1 (no) | 2000-12-18 | 2003-06-13 | Nye sulfonamider, fremstilling av disse, farmasoytiske preparater inneholdende slike,anvendelse av disse forbindelsene som medikament samt anvendelse av disse for fremstilling av medikament for behandling av lidelser. |
NO2014014C NO2014014I2 (no) | 2000-12-18 | 2014-06-05 | Macitentan, propylsulfamsyre [5-(4-brom-fenyl)-6-[2-(5-brom-pyrimidin-2-yloksy)-etoksy]-pyrimidin-4-yl]-amid eller et farmasøytisk akseptabelt salt derav; blant annet kravene 1, 5, 6 og 10 I søknaden (se vedlegg) |
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NO2014014C NO2014014I2 (no) | 2000-12-18 | 2014-06-05 | Macitentan, propylsulfamsyre [5-(4-brom-fenyl)-6-[2-(5-brom-pyrimidin-2-yloksy)-etoksy]-pyrimidin-4-yl]-amid eller et farmasøytisk akseptabelt salt derav; blant annet kravene 1, 5, 6 og 10 I søknaden (se vedlegg) |
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US (2) | US7094781B2 (xx) |
EP (2) | EP1345920B1 (xx) |
JP (1) | JP4245130B2 (xx) |
KR (1) | KR100819668B1 (xx) |
CN (1) | CN100432070C (xx) |
AR (1) | AR035610A1 (xx) |
AT (1) | ATE323079T1 (xx) |
AU (1) | AU2002227984B8 (xx) |
BE (1) | BE2014C019I2 (xx) |
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DE (1) | DE60118782T2 (xx) |
DK (1) | DK1345920T3 (xx) |
ES (1) | ES2260318T3 (xx) |
FR (1) | FR14C0017I2 (xx) |
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IL (2) | IL155805A0 (xx) |
LU (1) | LU92381I2 (xx) |
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MY (1) | MY129150A (xx) |
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NO (2) | NO324952B1 (xx) |
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PT (1) | PT1345920E (xx) |
WO (1) | WO2002053557A1 (xx) |
ZA (1) | ZA200303695B (xx) |
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