BG60831B2 - Нови сулфонамиди - Google Patents
Нови сулфонамиди Download PDFInfo
- Publication number
- BG60831B2 BG60831B2 BG098607A BG9860794A BG60831B2 BG 60831 B2 BG60831 B2 BG 60831B2 BG 098607 A BG098607 A BG 098607A BG 9860794 A BG9860794 A BG 9860794A BG 60831 B2 BG60831 B2 BG 60831B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- tert
- benzenesulfonamide
- butyl
- methoxy
- phenoxy
- Prior art date
Links
- 150000003456 sulfonamides Chemical class 0.000 title abstract description 8
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 6
- 206010020772 Hypertension Diseases 0.000 claims abstract description 5
- 208000028867 ischemia Diseases 0.000 claims abstract description 5
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 4
- 206010047163 Vasospasm Diseases 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 201000010099 disease Diseases 0.000 claims abstract 5
- -1 tert-butyl-dimethylsilyloxy Chemical group 0.000 claims description 250
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 116
- 150000001875 compounds Chemical class 0.000 claims description 101
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 239000012074 organic phase Substances 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 102000002045 Endothelin Human genes 0.000 claims description 11
- 108050009340 Endothelin Proteins 0.000 claims description 11
- 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 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 241000237536 Mytilus edulis Species 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 235000020638 mussel Nutrition 0.000 claims description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- XIZNSFKZKZTGNG-UHFFFAOYSA-N 2-butylbenzenesulfonamide Chemical compound CCCCC1=CC=CC=C1S(N)(=O)=O XIZNSFKZKZTGNG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- HGCNVBFWQCYTTB-UHFFFAOYSA-N 4-tert-butyl-n-[2-(furan-2-yl)-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2OC=CC=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 HGCNVBFWQCYTTB-UHFFFAOYSA-N 0.000 claims description 2
- OOALFRYRTFOMAS-UHFFFAOYSA-N 4-tert-butyl-n-[5-(4-fluoro-2-methoxyphenoxy)-6-(2-hydroxyethoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC(F)=CC=C1OC(C(=NC=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 OOALFRYRTFOMAS-UHFFFAOYSA-N 0.000 claims description 2
- ICGLTOLBTVCGPB-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyridin-3-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=NC=CC=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 ICGLTOLBTVCGPB-UHFFFAOYSA-N 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- KVUJNXSGZHFSBB-UHFFFAOYSA-N 2-ethyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxy-4-methylphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound CCC1=CC=CC=C1S(=O)(=O)NC1=NC=NC(OCCO)=C1OC1=CC=C(C)C=C1OC KVUJNXSGZHFSBB-UHFFFAOYSA-N 0.000 claims 1
- QSZPTRRZTQCBNH-UHFFFAOYSA-N 4-tert-butyl-n-[2-ethyl-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound C=1C=CC=C(OC)C=1OC=1C(OCCO)=NC(CC)=NC=1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 QSZPTRRZTQCBNH-UHFFFAOYSA-N 0.000 claims 1
- FUYIWALKTPDJRC-UHFFFAOYSA-N 4-tert-butyl-n-[5-(2-chloro-5-methoxyphenoxy)-6-(2-hydroxyethoxy)-2-methylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=C(Cl)C(OC=2C(=NC(C)=NC=2NS(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)OCCO)=C1 FUYIWALKTPDJRC-UHFFFAOYSA-N 0.000 claims 1
- TXJQLDNVVFRPGL-UHFFFAOYSA-N 4-tert-butyl-n-[5-(4-fluoro-2-methoxyphenoxy)-6-(2-hydroxyethoxy)-2-methylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC(F)=CC=C1OC(C(=NC(C)=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 TXJQLDNVVFRPGL-UHFFFAOYSA-N 0.000 claims 1
- KNFMAXWQURUHMD-UHFFFAOYSA-N 4-tert-butyl-n-[5-(4-fluoro-2-methoxyphenoxy)-6-(2-hydroxyethoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC(F)=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 KNFMAXWQURUHMD-UHFFFAOYSA-N 0.000 claims 1
- OKHMERPFPZODRR-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-2-(2-methoxyethyl)-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound C=1C=CC(OC)=CC=1OC=1C(OCCO)=NC(CCOC)=NC=1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 OKHMERPFPZODRR-UHFFFAOYSA-N 0.000 claims 1
- IPSKDUSDAACTJJ-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-2-[2-(2-hydroxyethoxy)ethyl]-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC(OC=2C(=NC(CCOCCO)=NC=2NS(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)OCCO)=C1 IPSKDUSDAACTJJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QOPGXVVGPBNZHE-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-propan-2-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C(C)C)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 QOPGXVVGPBNZHE-UHFFFAOYSA-N 0.000 claims 1
- BOUYHPQCWYVAAS-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(3-methoxyphenoxy)-2-thiophen-2-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC(OC=2C(=NC(=NC=2NS(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)C=2SC=CC=2)OCCO)=C1 BOUYHPQCWYVAAS-UHFFFAOYSA-N 0.000 claims 1
- HCAJUXSCGLHBQN-FQEVSTJZSA-N 4-tert-butyl-n-[6-[(2s)-2,3-dihydroxypropoxy]-2-(furan-3-yl)-5-(2-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C2=COC=C2)OC[C@@H](O)CO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 HCAJUXSCGLHBQN-FQEVSTJZSA-N 0.000 claims 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
- MXOSTENCGSDMRE-UHFFFAOYSA-N butyl-chloro-dimethylsilane Chemical compound CCCC[Si](C)(C)Cl MXOSTENCGSDMRE-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- QQXQAEWRSVZPJM-UHFFFAOYSA-N ethyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1 QQXQAEWRSVZPJM-UHFFFAOYSA-N 0.000 claims 1
- LPMIZTNZMHVVSS-UHFFFAOYSA-N ethyl 3-methyl-1,2-oxazole-5-carboxylate Chemical compound CCOC(=O)C1=CC(C)=NO1 LPMIZTNZMHVVSS-UHFFFAOYSA-N 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- CIQSELJNJWOORS-UHFFFAOYSA-N n-[5-(2-chlorophenoxy)-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=NC=NC(OCCO)=C1OC1=CC=CC=C1Cl CIQSELJNJWOORS-UHFFFAOYSA-N 0.000 claims 1
- DWZMFXBHYHDCKV-UHFFFAOYSA-N n-[5-(5-fluoro-2-methoxyphenoxy)-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound COC1=CC=C(F)C=C1OC(C(=NC=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 DWZMFXBHYHDCKV-UHFFFAOYSA-N 0.000 claims 1
- HNTMFYNZVGOMBK-UHFFFAOYSA-N n-[5-(5-fluoro-2-methoxyphenoxy)-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(F)C=C1OC(C(=NC=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=C1 HNTMFYNZVGOMBK-UHFFFAOYSA-N 0.000 claims 1
- MADUPCFUTOKGEM-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2,4,6-trichlorophenoxy)pyrimidin-4-yl]-2,4-dimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)NC1=NC=NC(OCCO)=C1OC1=C(Cl)C=C(Cl)C=C1Cl MADUPCFUTOKGEM-UHFFFAOYSA-N 0.000 claims 1
- HCLUVEKHLYUWMQ-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2,4,6-trichlorophenoxy)pyrimidin-4-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=NC=NC(OCCO)=C1OC1=C(Cl)C=C(Cl)C=C1Cl HCLUVEKHLYUWMQ-UHFFFAOYSA-N 0.000 claims 1
- FKUFTGMFORIVAP-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(trifluoromethyl)pyrimidin-4-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C(F)(F)F)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=C1 FKUFTGMFORIVAP-UHFFFAOYSA-N 0.000 claims 1
- KTLADBZPNNHCHM-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-methylpyrimidin-4-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(C)=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=C1 KTLADBZPNNHCHM-UHFFFAOYSA-N 0.000 claims 1
- PRTPSXRUUNCJGZ-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-methylpyrimidin-4-yl]naphthalene-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(C)=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 PRTPSXRUUNCJGZ-UHFFFAOYSA-N 0.000 claims 1
- ZHYADMKRGVVLCQ-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-phenylpyrimidin-4-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=CC=CC=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=C1 ZHYADMKRGVVLCQ-UHFFFAOYSA-N 0.000 claims 1
- HJQRNFPSYLHLAX-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-propylpyrimidin-4-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound C=1C=CC=C(OC)C=1OC=1C(OCCO)=NC(CCC)=NC=1NS(=O)(=O)C1=CC=C(C(C)C)C=C1 HJQRNFPSYLHLAX-UHFFFAOYSA-N 0.000 claims 1
- HOADLZGXXKFLFR-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-phenylethyl)pyrimidin-4-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC=NC(OCCO)=C1CCC1=CC=CC=C1 HOADLZGXXKFLFR-UHFFFAOYSA-N 0.000 claims 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000002792 vascular Effects 0.000 abstract description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 147
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 70
- 239000011734 sodium Substances 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 229910052708 sodium Inorganic materials 0.000 description 21
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- DFWRZHZPJJAJMX-UHFFFAOYSA-N propanimidamide;hydrochloride Chemical compound Cl.CCC(N)=N DFWRZHZPJJAJMX-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- GMHCEDDZKAYPLB-UHFFFAOYSA-N pyridine-2-carboximidamide;hydrochloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=N1 GMHCEDDZKAYPLB-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- LZIYBABLVXXFGZ-UHFFFAOYSA-N pyrimidine-2-carboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=NC=CC=N1 LZIYBABLVXXFGZ-UHFFFAOYSA-N 0.000 description 1
- 150000008512 pyrimidinediones Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 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
- 239000000376 reactant Substances 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- GQFIWFPBDXSASA-UHFFFAOYSA-M sodium;2-chlorophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1Cl GQFIWFPBDXSASA-UHFFFAOYSA-M 0.000 description 1
- ONFAAMBUOAGWSG-UHFFFAOYSA-M sodium;2-methylphenolate Chemical compound [Na+].CC1=CC=CC=C1[O-] ONFAAMBUOAGWSG-UHFFFAOYSA-M 0.000 description 1
- IIHZUISTNNNXQQ-UHFFFAOYSA-M sodium;3-methoxyphenolate Chemical compound [Na+].COC1=CC=CC([O-])=C1 IIHZUISTNNNXQQ-UHFFFAOYSA-M 0.000 description 1
- MYMOTVMHKLYQCM-UHFFFAOYSA-M sodium;4-methoxyphenolate Chemical compound [Na+].COC1=CC=C([O-])C=C1 MYMOTVMHKLYQCM-UHFFFAOYSA-M 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical class CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 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 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- IDELNEDBPWKHGK-UHFFFAOYSA-N thiobutabarbital Chemical compound CCC(C)C1(CC)C(=O)NC(=S)NC1=O IDELNEDBPWKHGK-UHFFFAOYSA-N 0.000 description 1
- 229940026152 thiobutabarbital Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JKCKRNYECSTMLV-UHFFFAOYSA-N thiophene-3-carboximidamide Chemical compound NC(=N)C=1C=CSC=1 JKCKRNYECSTMLV-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000011706 wistar kyoto rat Methods 0.000 description 1
Classifications
-
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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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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- A61P9/08—Vasodilators for multiple indications
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- A—HUMAN NECESSITIES
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- 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
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
- C07D401/02—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
-
- 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
- C07D403/12—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Lubricants (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Bipolar Transistors (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Glass Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH176091 | 1991-06-13 | ||
CH151692 | 1992-05-12 |
Publications (1)
Publication Number | Publication Date |
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BG60831B2 true BG60831B2 (bg) | 1996-04-30 |
Family
ID=25687870
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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BG098607A BG60831B2 (bg) | 1991-06-13 | 1994-02-28 | Нови сулфонамиди |
Country Status (34)
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US (1) | US5292740A (no) |
EP (1) | EP0526708B1 (no) |
JP (1) | JPH0730042B2 (no) |
KR (1) | KR100235507B1 (no) |
AT (1) | ATE197044T1 (no) |
AU (1) | AU653604B2 (no) |
BG (1) | BG60831B2 (no) |
BR (1) | BR9202219A (no) |
CA (1) | CA2071193C (no) |
CY (2) | CY2306B1 (no) |
CZ (1) | CZ281434B6 (no) |
DE (2) | DE10299047I2 (no) |
DK (1) | DK0526708T3 (no) |
DZ (1) | DZ1587A1 (no) |
EE (1) | EE03028B1 (no) |
ES (1) | ES2152222T4 (no) |
FI (1) | FI112216B (no) |
GR (1) | GR3035162T3 (no) |
HU (2) | HU221203B1 (no) |
IE (1) | IE921920A1 (no) |
IL (1) | IL102138A (no) |
IS (1) | IS2054B (no) |
LU (2) | LU90975I2 (no) |
MX (1) | MX9202747A (no) |
NL (1) | NL300097I1 (no) |
NO (2) | NO303826B1 (no) |
NZ (1) | NZ243074A (no) |
PT (1) | PT526708E (no) |
RO (1) | RO111268B (no) |
RU (1) | RU2086544C1 (no) |
SG (1) | SG54209A1 (no) |
SK (1) | SK279006B6 (no) |
TW (1) | TW222625B (no) |
ZA (1) | ZA924126B (no) |
Families Citing this family (187)
Publication number | Priority date | Publication date | Assignee | Title |
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US5571821A (en) * | 1993-05-20 | 1996-11-05 | Texas Biotechnology Corporation | Sulfonamides and derivatives thereof that modulate the activity of endothelin |
US5962490A (en) | 1987-09-25 | 1999-10-05 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
US5591761A (en) * | 1993-05-20 | 1997-01-07 | Texas Biotechnology Corporation | Thiophenyl-, furyl-and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
US5594021A (en) * | 1993-05-20 | 1997-01-14 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl sulfonamides and derivatives thereof that modulate the activity of endothelin |
US5514691A (en) * | 1993-05-20 | 1996-05-07 | Immunopharmaceutics, Inc. | N-(4-halo-isoxazolyl)-sulfonamides and derivatives thereof that modulate the activity of endothelin |
AU641931B2 (en) * | 1989-08-30 | 1993-10-07 | M-I L.L.C. | Disposable oxide carrier for scavenging hydrogen sulfide |
US5736509A (en) * | 1990-12-14 | 1998-04-07 | Texas Biotechnology Corporation | Cyclic peptide surface feature mimics of endothelin |
US5378715A (en) * | 1992-02-24 | 1995-01-03 | Bristol-Myers Squibb Co. | Sulfonamide endothelin antagonists |
TW224462B (no) * | 1992-02-24 | 1994-06-01 | Squibb & Sons Inc | |
US5514696A (en) * | 1992-05-06 | 1996-05-07 | Bristol-Myers Squibb Co. | Phenyl sulfonamide endothelin antagonists |
NZ247440A (en) * | 1992-05-06 | 1995-04-27 | Squibb & Sons Inc | Phenyl sulphonamide derivatives, preparation and pharmaceutical compositions thereof |
US5420123A (en) * | 1992-12-21 | 1995-05-30 | Bristol-Myers Squibb Company | Dibenzodiazepine endothelin antagonists |
US5352800A (en) * | 1993-03-11 | 1994-10-04 | Merck & Co., Inc. | Process for the production of a novel endothelin antagonist |
US5401745A (en) * | 1993-03-19 | 1995-03-28 | Merck & Co., Inc. | Quinazolinones substituted with phenoxyphenylacetic acid derivatives |
US5334598A (en) * | 1993-03-19 | 1994-08-02 | Merck & Co., Inc. | Six-membered ring fused imidazoles substituted with phenoxyphenylacetic acid derivatives |
US5374638A (en) * | 1993-03-19 | 1994-12-20 | Merck & Co., Inc. | Six membered ring fused imidazoles substituted with phenoxyphenylacetic acid derivatives used to treat asthma |
US5767310A (en) * | 1993-03-19 | 1998-06-16 | Merck & Co., Inc. | Phenoxyphenylacetic acid derivatives |
US5420133A (en) * | 1993-03-19 | 1995-05-30 | Merck & Co., Inc. | Quinazolinones substituted with phenoxyphenylacetic acid derivatives |
EP0626174A3 (en) | 1993-04-21 | 1996-01-03 | Takeda Chemical Industries Ltd | Method and composition for the prophylaxis and / or treatment of underactive organs. |
US6376523B1 (en) | 1994-05-20 | 2002-04-23 | Texas Biotechnology Corporation | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
US6342610B2 (en) | 1993-05-20 | 2002-01-29 | Texas Biotechnology Corp. | N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
US6541498B2 (en) | 1993-05-20 | 2003-04-01 | Texas Biotechnology | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
US6613804B2 (en) | 1993-05-20 | 2003-09-02 | Encysive Pharmaceuticals, Inc. | Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin |
US6030991A (en) * | 1993-05-20 | 2000-02-29 | Texas Biotechnology Corp. | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
US6087324A (en) * | 1993-06-24 | 2000-07-11 | Takeda Chemical Industries, Ltd. | Sustained-release preparation |
TW394761B (en) * | 1993-06-28 | 2000-06-21 | Hoffmann La Roche | Novel Sulfonylamino Pyrimidines |
EP0634175B1 (de) * | 1993-07-15 | 2001-01-10 | F. Hoffmann-La Roche Ag | Pharmazeutische Kombination, die einen Hemmer des Renin-Angiotensin-Systems und einen Endothelin-Antagonisten enthält |
US5686478A (en) * | 1993-07-20 | 1997-11-11 | Merck & Co. Inc. | Endothelin antagonists |
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DE1545944A1 (de) * | 1964-06-19 | 1969-12-11 | Hoffmann La Roche | Verfahren zur Herstellung von neuen Sulfonamiden der Pyrimidinreihe |
AU6623690A (en) * | 1990-10-29 | 1992-05-26 | Ibrahim Raouf Shimi | Novel sulfamide derivatives, a method for obtaining them and their use as a drug |
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1992
- 1992-01-31 RU SU925011139A patent/RU2086544C1/ru active Protection Beyond IP Right Term
- 1992-06-04 DE DE10299047C patent/DE10299047I2/de active Active
- 1992-06-04 DK DK92109431T patent/DK0526708T3/da not_active Application Discontinuation
- 1992-06-04 AT AT92109431T patent/ATE197044T1/de active
- 1992-06-04 DE DE59209872T patent/DE59209872D1/de not_active Expired - Lifetime
- 1992-06-04 EP EP92109431A patent/EP0526708B1/de not_active Expired - Lifetime
- 1992-06-04 SG SG1996004376A patent/SG54209A1/en unknown
- 1992-06-04 ES ES92109431T patent/ES2152222T4/es not_active Expired - Lifetime
- 1992-06-04 PT PT92109431T patent/PT526708E/pt unknown
- 1992-06-05 ZA ZA924126A patent/ZA924126B/xx unknown
- 1992-06-09 IL IL10213892A patent/IL102138A/en active Protection Beyond IP Right Term
- 1992-06-09 MX MX9202747A patent/MX9202747A/es active IP Right Grant
- 1992-06-09 AU AU18121/92A patent/AU653604B2/en not_active Expired
- 1992-06-09 US US07/896,015 patent/US5292740A/en not_active Expired - Lifetime
- 1992-06-09 NZ NZ243074A patent/NZ243074A/en not_active IP Right Cessation
- 1992-06-10 HU HU9201930A patent/HU221203B1/hu active Protection Beyond IP Right Term
- 1992-06-10 DZ DZ920066A patent/DZ1587A1/fr active
- 1992-06-10 JP JP4174993A patent/JPH0730042B2/ja not_active Expired - Fee Related
- 1992-06-11 RO RO92-0780A patent/RO111268B/ro unknown
- 1992-06-12 CA CA002071193A patent/CA2071193C/en not_active Expired - Lifetime
- 1992-06-12 FI FI922746A patent/FI112216B/fi active Protection Beyond IP Right Term
- 1992-06-12 IS IS3877A patent/IS2054B/is unknown
- 1992-06-12 CZ CS921804A patent/CZ281434B6/cs not_active IP Right Cessation
- 1992-06-12 SK SK1804-92A patent/SK279006B6/sk not_active IP Right Cessation
- 1992-06-12 NO NO922323A patent/NO303826B1/no not_active IP Right Cessation
- 1992-06-12 KR KR1019920010205A patent/KR100235507B1/ko not_active IP Right Cessation
- 1992-06-15 BR BR929202219A patent/BR9202219A/pt not_active Application Discontinuation
- 1992-07-01 IE IE192092A patent/IE921920A1/en active Protection Beyond IP Right Term
- 1992-11-18 TW TW081109235A patent/TW222625B/zh not_active IP Right Cessation
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1994
- 1994-02-28 BG BG098607A patent/BG60831B2/bg unknown
- 1994-11-23 EE EE9400322A patent/EE03028B1/xx unknown
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1995
- 1995-06-20 HU HU95P/P00261P patent/HU211683A9/hu unknown
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2000
- 2000-12-28 GR GR20000402849T patent/GR3035162T3/el unknown
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2001
- 2001-11-01 CY CY0100036A patent/CY2306B1/xx unknown
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2002
- 2002-09-02 NL NL300097C patent/NL300097I1/nl unknown
- 2002-10-16 LU LU90975C patent/LU90975I2/fr unknown
- 2002-10-16 LU LU90976C patent/LU90976I2/fr unknown
- 2002-10-29 NO NO2002012C patent/NO2002012I2/no unknown
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2004
- 2004-10-27 CY CY2004005C patent/CY2004005I2/el unknown
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