IL102138A - Sulfonamides, their preparation and pharmaceutical preparations containing sulfonamides - Google Patents
Sulfonamides, their preparation and pharmaceutical preparations containing sulfonamidesInfo
- Publication number
- IL102138A IL102138A IL10213892A IL10213892A IL102138A IL 102138 A IL102138 A IL 102138A IL 10213892 A IL10213892 A IL 10213892A IL 10213892 A IL10213892 A IL 10213892A IL 102138 A IL102138 A IL 102138A
- Authority
- IL
- Israel
- Prior art keywords
- methoxy
- butyl
- phenoxy
- tert
- pyrimidin
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000003456 sulfonamides Chemical class 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title description 9
- 239000000543 intermediate Substances 0.000 title description 4
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
- 208000035475 disorder Diseases 0.000 claims abstract description 10
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 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
- 239000000126 substance Substances 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 101
- -1 methylenedioxy Chemical group 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 102000002045 Endothelin Human genes 0.000 claims description 10
- 108050009340 Endothelin Proteins 0.000 claims 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 description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
- 229910052701 rubidium 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
- HXIYCKAAQPHZBM-UHFFFAOYSA-N 3-methyl-1,2-oxazole-5-carboxylic acid Chemical compound CC=1C=C(C(O)=O)ON=1 HXIYCKAAQPHZBM-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 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
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- SSZLBBTUZKTYAT-UHFFFAOYSA-N 2-ethyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-methylpyrimidin-4-yl]benzenesulfonamide Chemical compound CCC1=CC=CC=C1S(=O)(=O)NC1=NC(C)=NC(OCCO)=C1OC1=CC=CC=C1OC SSZLBBTUZKTYAT-UHFFFAOYSA-N 0.000 claims description 2
- ZBPVZZIHQFWIIJ-UHFFFAOYSA-N 4-(2,2-dimethylpropyl)-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(CC(C)(C)C)C=C1 ZBPVZZIHQFWIIJ-UHFFFAOYSA-N 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
- JRYSTBVLGFETLC-UHFFFAOYSA-N 4-tert-butyl-n-[2-(furan-3-yl)-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C2=COC=C2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 JRYSTBVLGFETLC-UHFFFAOYSA-N 0.000 claims description 2
- OLQQNLDLUWGUOC-UHFFFAOYSA-N 4-tert-butyl-n-[5-(2-chloro-5-methoxyphenoxy)-2-ethyl-6-(2-methylsulfinylethoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound C=1C(OC)=CC=C(Cl)C=1OC=1C(OCCS(C)=O)=NC(CC)=NC=1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 OLQQNLDLUWGUOC-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- SPORGDTWHZWWFO-UHFFFAOYSA-N 4-tert-butyl-n-[5-(2-chlorophenoxy)-6-(2-hydroxyethoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=NC=NC(OCCO)=C1OC1=CC=CC=C1Cl SPORGDTWHZWWFO-UHFFFAOYSA-N 0.000 claims description 2
- XNZPXOFWYQMBNC-UHFFFAOYSA-N 4-tert-butyl-n-[5-(2-ethoxyphenoxy)-6-(2-hydroxyethoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound CCOC1=CC=CC=C1OC(C(=NC=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 XNZPXOFWYQMBNC-UHFFFAOYSA-N 0.000 claims description 2
- XRCMKXQGFCYJRK-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-2-[2-(2-hydroxyethoxy)ethyl]-5-(2-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(CCOCCO)=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 XRCMKXQGFCYJRK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- LIARTULJNMGSNS-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-2-methyl-5-(2-methylsulfanylphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound CSC1=CC=CC=C1OC(C(=NC(C)=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 LIARTULJNMGSNS-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
- CSHBWFOWZFSIDZ-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyridin-2-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CC=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 CSHBWFOWZFSIDZ-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
- HEBWMVUSTSZAMZ-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyridin-4-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=CN=CC=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 HEBWMVUSTSZAMZ-UHFFFAOYSA-N 0.000 claims description 2
- DQGJBNBZQJTIHE-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-thiophen-2-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2SC=CC=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 DQGJBNBZQJTIHE-UHFFFAOYSA-N 0.000 claims description 2
- NFEWKJNARXIISE-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-thiophen-3-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C2=CSC=C2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 NFEWKJNARXIISE-UHFFFAOYSA-N 0.000 claims description 2
- KPJXDJRWFUDSEA-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 KPJXDJRWFUDSEA-UHFFFAOYSA-N 0.000 claims description 2
- MBDSOEMOPHGXEG-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methylphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound CC1=CC=CC=C1OC(C(=NC=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 MBDSOEMOPHGXEG-UHFFFAOYSA-N 0.000 claims description 2
- FCJLEBQUOPUDCV-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(3-methoxyphenoxy)-2-pyrimidin-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=2N=CC=CN=2)OCCO)=C1 FCJLEBQUOPUDCV-UHFFFAOYSA-N 0.000 claims description 2
- ZNXOKLWCOWOECF-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC(OC=2C(=NC=NC=2NS(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)OCCO)=C1 ZNXOKLWCOWOECF-UHFFFAOYSA-N 0.000 claims description 2
- DAQDYBGMTAIPFL-GOSISDBHSA-N 4-tert-butyl-n-[6-[(2r)-2,3-dihydroxypropoxy]-5-(2-methoxyphenoxy)-2-methylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(C)=N1)OC[C@H](O)CO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 DAQDYBGMTAIPFL-GOSISDBHSA-N 0.000 claims description 2
- JANQEUYONJBENB-HXUWFJFHSA-N 4-tert-butyl-n-[6-[(2r)-2,3-dihydroxypropoxy]-5-(2-methoxyphenoxy)-2-thiophen-3-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C2=CSC=C2)OC[C@H](O)CO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 JANQEUYONJBENB-HXUWFJFHSA-N 0.000 claims description 2
- 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 description 2
- BDFRYTNUXQDOHF-IBGZPJMESA-N 4-tert-butyl-n-[6-[(2s)-2,3-dihydroxypropoxy]-5-(2-methoxyphenoxy)-2-thiophen-2-ylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2SC=CC=2)OC[C@@H](O)CO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 BDFRYTNUXQDOHF-IBGZPJMESA-N 0.000 claims description 2
- SHEIXBFGSRILDU-UHFFFAOYSA-N ClC1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=C(C=CC(=C1)F)OC)OCCO Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=C(C=CC(=C1)F)OC)OCCO SHEIXBFGSRILDU-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 206010047163 Vasospasm Diseases 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- FMEXEIWSIXFMHL-UHFFFAOYSA-N ethyl 2-[5-[[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]sulfamoyl]-2-methoxyphenoxy]acetate Chemical compound C1=C(OC)C(OCC(=O)OCC)=CC(S(=O)(=O)NC=2C(=C(OCCO)N=CN=2)OC=2C(=CC=CC=2)OC)=C1 FMEXEIWSIXFMHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 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 description 2
- 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 description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 4
- 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
- DUKFXEPSTLLSTI-UHFFFAOYSA-N 4-chloro-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-methylpyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(C)=N1)OCCO)=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 DUKFXEPSTLLSTI-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
- YTBGKHFJEQITFY-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(1-oxidopyridin-1-ium-2-yl)pyrimidin-4-yl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2[N+](=CC=CC=2)[O-])OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 YTBGKHFJEQITFY-UHFFFAOYSA-N 0.000 claims 1
- HVRDENHNEUGHGW-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-phenylpyrimidin-4-yl]benzenesulfonamide 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)C=C1 HVRDENHNEUGHGW-UHFFFAOYSA-N 0.000 claims 1
- VRFTVVXDJRJGNL-UHFFFAOYSA-N 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(3-methoxy-4-methylphenoxy)pyrimidin-4-yl]benzenesulfonamide Chemical compound C1=C(C)C(OC)=CC(OC=2C(=NC=NC=2NS(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)OCCO)=C1 VRFTVVXDJRJGNL-UHFFFAOYSA-N 0.000 claims 1
- DRIHNVYRUGBDHI-QFIPXVFZSA-N 4-tert-butyl-n-[6-[(2s)-2,3-dihydroxypropoxy]-5-(2-methoxyphenoxy)-2-(4-methoxyphenyl)pyrimidin-4-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C(N=C1OC[C@@H](O)CO)=NC(NS(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)=C1OC1=CC=CC=C1OC DRIHNVYRUGBDHI-QFIPXVFZSA-N 0.000 claims 1
- 101150052863 THY1 gene Proteins 0.000 claims 1
- GJPICJJJRGTNOD-UHFFFAOYSA-N bosentan Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 GJPICJJJRGTNOD-UHFFFAOYSA-N 0.000 claims 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 1
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- VAIZGPPJYYUVTN-UHFFFAOYSA-N n-[6-chloro-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(Cl)=C1OC1=C(Cl)C=C(Cl)C=C1Cl VAIZGPPJYYUVTN-UHFFFAOYSA-N 0.000 description 1
- WZNHFPAKUCGEDQ-UHFFFAOYSA-N n-[6-chloro-5-(3-methoxyphenoxy)-2-methylpyrimidin-4-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=CC(OC=2C(=NC(C)=NC=2Cl)NS(=O)(=O)C=2C=CC(=CC=2)C(C)C)=C1 WZNHFPAKUCGEDQ-UHFFFAOYSA-N 0.000 description 1
- SWBLLSQMOMPTMC-UHFFFAOYSA-N naphthalene-2-sulfonamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)N)=CC=C21 SWBLLSQMOMPTMC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 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
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- DFWRZHZPJJAJMX-UHFFFAOYSA-N propanimidamide;hydrochloride Chemical compound Cl.CCC(N)=N DFWRZHZPJJAJMX-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 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
- 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
- 230000002685 pulmonary effect Effects 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
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 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
- 230000008707 rearrangement Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229940023144 sodium glycolate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 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
- 230000009870 specific binding Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 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
- 238000002560 therapeutic procedure Methods 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
- URAGJMBGNVOIJC-UHFFFAOYSA-N thiophene-2-carboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=CS1 URAGJMBGNVOIJC-UHFFFAOYSA-N 0.000 description 1
- CAUZIIYPBLBRFI-UHFFFAOYSA-N thiophene-3-carboximidamide;hydrochloride Chemical compound Cl.NC(=N)C=1C=CSC=1 CAUZIIYPBLBRFI-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
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular 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
- 238000010626 work up procedure 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
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- 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
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- 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
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- 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
- C07D401/02—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)
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- 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)
- Glass Compositions (AREA)
- Bipolar Transistors (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (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 (2)
Publication Number | Publication Date |
---|---|
IL102138A0 IL102138A0 (en) | 1993-01-14 |
IL102138A true IL102138A (en) | 1996-09-12 |
Family
ID=25687870
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL10213892A IL102138A (en) | 1991-06-13 | 1992-06-09 | Sulfonamides, their preparation and pharmaceutical preparations containing sulfonamides |
Country Status (34)
Country | Link |
---|---|
US (1) | US5292740A (fr) |
EP (1) | EP0526708B1 (fr) |
JP (1) | JPH0730042B2 (fr) |
KR (1) | KR100235507B1 (fr) |
AT (1) | ATE197044T1 (fr) |
AU (1) | AU653604B2 (fr) |
BG (1) | BG60831B2 (fr) |
BR (1) | BR9202219A (fr) |
CA (1) | CA2071193C (fr) |
CY (2) | CY2306B1 (fr) |
CZ (1) | CZ281434B6 (fr) |
DE (2) | DE59209872D1 (fr) |
DK (1) | DK0526708T3 (fr) |
DZ (1) | DZ1587A1 (fr) |
EE (1) | EE03028B1 (fr) |
ES (1) | ES2152222T4 (fr) |
FI (1) | FI112216B (fr) |
GR (1) | GR3035162T3 (fr) |
HU (2) | HU221203B1 (fr) |
IE (1) | IE921920A1 (fr) |
IL (1) | IL102138A (fr) |
IS (1) | IS2054B (fr) |
LU (2) | LU90975I2 (fr) |
MX (1) | MX9202747A (fr) |
NL (1) | NL300097I1 (fr) |
NO (2) | NO303826B1 (fr) |
NZ (1) | NZ243074A (fr) |
PT (1) | PT526708E (fr) |
RO (1) | RO111268B (fr) |
RU (1) | RU2086544C1 (fr) |
SG (1) | SG54209A1 (fr) |
SK (1) | SK279006B6 (fr) |
TW (1) | TW222625B (fr) |
ZA (1) | ZA924126B (fr) |
Families Citing this family (187)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
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 |
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 |
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KR102004422B1 (ko) | 2012-12-20 | 2019-07-26 | 제일약품주식회사 | 보센탄 일수화물의 제조방법, 이에 사용되는 신규 중간체 및 이의 제조방법 |
AP2015008621A0 (en) | 2013-02-14 | 2015-07-31 | Novartis Ag | Substituted bisphenyl butanoic nep 'neutral endopeptidase' inhibitors |
JP2016527249A (ja) | 2013-07-25 | 2016-09-08 | ノバルティス アーゲー | 合成アペリンポリペプチドのバイオコンジュゲート |
UY35670A (es) | 2013-07-25 | 2015-02-27 | Novartis Ag | Polipéptidos cíclicos para el tratamiento de insuficiencia cardíaca |
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KR20170103970A (ko) | 2015-01-23 | 2017-09-13 | 노파르티스 아게 | 개선된 반감기를 갖는 합성 아펠린 지방산 접합체 |
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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
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- 1992-06-04 EP EP92109431A patent/EP0526708B1/fr not_active Expired - Lifetime
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