FI116622B - Aryl- och heteroarylsulfonamidderivat, framställning av dem och användning av dem som endotelinantagonister - Google Patents
Aryl- och heteroarylsulfonamidderivat, framställning av dem och användning av dem som endotelinantagonister Download PDFInfo
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- FI116622B FI116622B FI972629A FI972629A FI116622B FI 116622 B FI116622 B FI 116622B FI 972629 A FI972629 A FI 972629A FI 972629 A FI972629 A FI 972629A FI 116622 B FI116622 B FI 116622B
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- methoxyphenoxy
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- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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Claims (13)
1. I > » » » I f I I • I I · • * • t * » * * t I ( » 116622 77 l.Föreningar med formeln I och farmaceutiskt an-vändbara salter därav, 5 R1S02NH Γί °R2 R3 x OCH2(CR"R»)„CH2Z vari R1 betecknar (lägre alkyl)fenyl, (lägre alkoxi)fen-10 yl, (lägre alkyltio)fenyl, trifluormetylfenyl, (lägre al-kylen)dioxifenyl eller (lägre alkyl)pyridyl; R2 betecknar fenyl substituerad med lägre alkoxi och/eller halogen; R3 betecknar väte, cyan, fenyl, 5-tetrazolyl, kar-15 boxi, (lägre alkoxi)karbonyl eller -CONR5R6; R5 betecknar väte; R6 betecknar fenyl, som eventuellt är substituerad ; med lägre alkoxi, hydroxi, hydroxi(lägre alkyl), karboxi, (lägre alkylen) dioxi eller fenyl; eller pyridyl, 5-tetra-20 zolyl, lägre alkyl, cyan (lägre alkyl), hydroxi (lägre al-'· ; kyl), di(lägre alkyl) amino(lägre alkyl), karboxi(lägre al- • I kyl), (lägre alkoxi) karbonyl (lägre alkyl), (lägre alkoxi)-karbonylamino (lägre alkyl) eller fenyl (lägre alkoxi) kar- * « * bonyl; eller
25 NR5R6 är morfolino, 2,6-dimetylmorfolino, piperidi- no, piperazino, N4-lägre alkylpiperazino, N4-formylpipe-razino eller N4-lägre alkoxikarbonylpiperazino; ·* Ra betecknar väte, lägre alkyl eller hydroxi; ·· Rb betecknar väte eller lägre alkyl; ' , 30 Z betecknar hydroxi eller, när Ra är väte eller • lägre alkyl, en rest —0C(0)NHR8; R8 betecknar fenyl eller pyridyl; 116622 78 X betecknar kväve eller en CH-grupp; n betecknar ett heltat O, 1 eller 2; och "lägre" betecknar att ifrägavarande grupper inne-häller 1-7 kolatomer. 5
2. Föreningar enligt patentkravet 1, kanne - tecknade därav, att Z är —0C(0)NHR8.
3. Föreningar enligt patentkravet 1, kanne -tecknade därav, att Z är hydroxi.
4. Föreningar enligt patentkrav 2, 10 pyridin-2-ylkarbaminsyra-2-[3-(4-t-butylbensensul- fonylamino)-2-(2-metoxifenoxi)-5-morfolin-4-karbonyl)fen-oxi]etylester, pyridin-2-ylkarbaminsyra-2-[3-(4-t-butylbensensul-fonylamino)-2-(2-metoxifenoxi)-5-(piperidin-1-karbonyl)-15 fenoxi]etylester, pyridin-2-ylkarbaminsyra-2-[3-(4-t-butylbensensul-fonylamino)-2-(2-metoxifenoxi)-5-fenylkarbamoylfenoxi]-etylester, metyl-3-(benso[1,3]dioxol-5-sulfonylamino)-4-(2-20 metoxifenoxi)-5-[2-(pyridin-2-ylkarbamoyloxi)etoxi]bensoat, pyridin-2-ylkarbaminsyra-2-[3-(benso[1,3]dioxol-5-sulfonylamino)-2-(2-metoxifenoxi)-5-(morfolin-4-karbonyl)-• fenoxi]etylester, ·· etyl-4-{3-(benso[1,3]dioxol-5-sulfonylamino)-4-(2- j ! 25 metoxifenoxi)-5-[2-(pyridin-2-ylkarbamoyloxi)etoxi]benso- : ·,: yl} piperazin-l-karboxylat, » · • pyridin-2-ylkarbaminsyra-2- [3- (benso [1, 3] dioxol-5- sulfonylamino) -5-isobutylkarbamoyl-2- (2-metoxifenoxi) fenoxi] etylester, . . 30 pyridin-2-ylkarbaminsyra-2-[3-(benso[1,3]dioxol-5- » ♦ sulf onylamino) -5-isopropylkarbamoyl-2- (2-metoxifenoxi) fen- ;*’ oxi)etylester, » metyl-3- (4-metoxibensensulfonylamino) -4- (2-metoxi- ;*·· fenoxi) -5- [2- (pyridin-2-ylkarbamoyloxi) etoxi]bensoat, * % 79 116622 pyridin-2-ylkarbaminsyra-2-[3-(4-metoxibensensul-fonylamino)-2-(2-metoxifenoxi)-5-(morfolin-4-karbonyl)fen-oxi]etylester, etyl-4-{4-(2-metoxifenoxi)-3-(4-metylsulfanylben-5 sensulfonylamino)-5-[2-(pyridin-2-ylkarbamoyloxi)etoxi]-bensoyl}piperazin-l-karboxylat, metyl-4-(2-metoxifenoxi)-3-[2-(pyridin-2-yl-karba-moyloxi)etoxi]-5-(toluen-4-sulfonylamino)bensoat, pyridin-2-ylkarbaminsyra-2-[2-(2-metoxifenoxi)-5-10 (morfolin-4-karbonyl)-3-(toluen-4-sulfonylamino)fenoxi]etylester, metyl-3-(4-tertbutyl-bensensulfonylamino)-4-(2-klor- 5-metoxifenoxi)-5-[2-(pyridin-2-ylkarbamoyloxi)etoxi]bensoat, pyridin-2-ylkarbaminsyra-2-[3-(4-t-butylbensensul-15 fonylamino)-2-(2-klor-5-metoxifenoxi)-5-(morfolin-4-kar-bonyl)fenoxi]etylester, metyl-3-(4-t-butylbensensulfonylamino)-4-(3-met-oxifenoxi)-5-[2-(pyridin-2-ylkarbamoyloxi)-etoxi]-bensoat, pyridin-2-ylkarbaminsyra-2-[3-(4-t-butylbensensul-20 fonylamino)-2-(3-metoxifenoxi)-5-(morfolin-4-karbonyl)fenoxi] etylester, ;·. pyridin-2-ylkarbaminsyra-2- [3- (4-t-butylbensensul- * _. _ . fonylamino)-2-(3-metoxifenoxi)-5-(3-metoxifenylkarbamoyl) - fenoxi]etylester, • » · ;*·[ 25 pyridin-2-ylkarbaminsyra-2-[3-(4-t-butylbensensul- * » · *· '·* fonylamino) -2-( 3-metoxifenoxi) -5-f enylkarbamoyl fenoxi ] et- t I : '· ylester, v * pyridin-2-ylkarbaminsyra-2-[3-(4-metoxibensensul- fonylamino)-2-(3-metoxifenoxi)-5-fenylkarbamoylfenoxi]et- ; 30 ylester, * » · {3-(4-t-butylbensensulfonylamino)-4-(2-metoxifenoxi ) -5- [2- (pyr idin- 2- ylkarbamoyloxi ) etoxi ] bensoyl amino } ät-* tiksyra, ; 5 » * pyridin-2-ylkarbaminsyra-2-[3-(4-t-butylfenylsul-*. * 35 fonylamino)-2-(2-metoxifenoxi)fenoxi]etylester, 116622 80 pyridin-2-ylkarbaminsyra-2-[3-(4-t-butylfenylsul-fonylamino)-2-(2-klor-5-metoxifenoxi)etylester, pyridin-2-ylkarbaminsyra-2-[2-(2-metoxifenoxi)-3-(4-metylsulfanylbensensulfonylamino)-5-(morfolin-4-karbon-5 yl)fenoxi]etylester.
5.Föreningar enligt patentkrav 3, metyl-3-(4-t-butylfenylsulfonylamino)-5-(2-hydroxi-etoxi)-4-(2-metoxifenoxi)bensoat, 3-(4-t-butylbensensulfonylamino)-5-(2-hydroxietoxi)-10 4-(2-metoxifenoxi)bensoesyra, 3- (4-t-butylbensensulfonylamino)-4-(2-klor-5-metoxi-fenoxi)-5-(2-hydroxietoxi)-N-fenylbensamid, 4- t-butyl-N-[3-(2-hydroxietoxi)-2-(2-metoxifenoxi)- 5-(morfolin-4-karbonyl)fenyl]bensensulfonamid, 15 4-t-butyl-N-[3-(2-hydroxietoxi)-2-(2-metoxifenoxi)- 5-(piperidin-l-karbonyl)fenyl]bensensulfonamid, 3-(4-t-butylbensensulfonylamino)-5-(2-hydroxietoxi)- 4-(2-metoxifenoxi)-N-fenylbensamid, 3-(4-t-butylbensensulfonylamino)-N-cyanmetyl-5-(2-20 hydroxietoxi)-4- (2-metoxifenoxi)bensamid, 3-(4-t-butylbensensulfonylamino)-N-(2-dimetylamino-etyl)-5-(2-hydroxietoxi)-4-(2-metoxifenoxi)bensamid, * t-butyl-{2-[3-(4-t-butylbensensulfonylamino)-5-(2- • · -.*·· hydroxietoxi) -4- (2-metoxifenoxi) bensoylamino] etyl} karbamat, : 25 [3-(4-t-butylbensensulfonylamino)-5-(2-hydroxiet- oxi) -4- (2-metoxifenoxi) bensoylamino] ättiksyra, • · metyl-3- (benso [1,3] dioxol-5-sulfonylamino) -5- (2-hydroxietoxi) -4- (2-metoxifenoxi)bensoat, 3-(benso[1,3]dioxol-5-sulfonylamino)-5-(2-hydroxiet- . . 30 oxi)-4-(2-metoxifenoxi)bensoesyra, ;:/ benso [1,3] dioxol-5-sulfonsyra- [3- (2-hydroxietoxi) -2- ;· (2-metoxifenoxi) -5- (morfolin-4-karbonyl) fenyl] amid, :·: etyl-N4- [3-benso [1,3] dioxol-5-sulfonylamino) -5- (2- :·*· hydroxietoxi) -4- (2-metoxifenoxi) bensoyl] piperazin-l-karboxy- 35 lat, i » » · t 116622 81 3-(benso[l,3]dioxol-5-sulfonylamino)-5-(2-hydroxi-etoxi)-N-isobutyl-4-(2-metoxifenoxi)bensamid, 3-(benso[1,3]dioxol-5-sulfonylamino)-5-(2-hydroxi-etoxi)-N-isopropyl-4-(2-metoxifenoxi)bensamid, 5 3-(benso[l,3]dioxol-5-sulfonylamino)-5-(2-hydroxi- etoxi)-N-(2-hydroxietyl)-4-(2-metoxifenoxi)bensamid, metyl-3-(2-hydroxietoxi)-5-(4-metoxibensensulfonylamino) -4-(2-metoxifenoxi)bensoat, 3- (2-hydroxietoxi)-5-(4-metoxibensensulfonylamino)- 10 4-(2-metoxifenoxi)bensoesyra, N-[3-(2-hydroxietoxi)-2-(2-metoxifenoxi)-5-(morfo-lin-4-karbonyl)fenyl]-4-metoxibensensulfonamid, metyl-3-(2-hydroxietoxi)-4-(2-metoxifenoxi)-5-(4-metylsulfanylbensensulfonylamino)bensoat, 15 3—(2-hydroxietoxi)-4-(2-metoxifenoxi)-5-(4-metylsul- fanylbensensulfonylamino)bensoesyra, N-[3-(2-hydroxietoxi)-2-(2-metoxifenoxi)-5-(morfo-lin-4-karbonyl)fenyl]-4-metylsulfanylbensensulfonamid, etyl-4-[3-(2-hydroxietoxi)-4-(2-metoxifenoxi)-5-(4-20 metylsulfanylbensensulfonylamino) bensoyl ] piperazin-l-karb-oxylat, metyl-3-(2-hydroxietoxi)-4-(3-metoxifenoxi)-5-(tolu-; , en-4-sulfonylamino)-bensoat, ’· 3-(2-hydroxietoxi)-4-(2-metoxifenoxi)-5-(toluen-4- 25 sulfonylamino) bensoesyra, » · ·,**: N- [3- (2-hydroxietoxi) -2- (2-metoxifenoxi) -5- (morfo- \ lin-4-karbonyl) fenyl] -4-metylbensensulfonamid, metyl-3- (4-t-butylbensensulfonylamino) -4- (2-klor-5- metoxifenoxi)-5- (2-hydroxietoxi)bensoat, : 30 3-(4-t-butylbensensulfonylamino)-4-(2-klor-5-metoxi- * » » · ,fenoxi) -5- (2-hydroxietoxi)bensoesyra, 4- t-butyl-N- [2- (2-klor-5-metoxifenoxi) -3- (2-hydroxi- ' * etoxi)-5-(morfolin-4-karbonyl)fenyl]bensensulfonamid, metyl-4- (2-klor-5-metoxifenoxi) -3- (2-hydroxietoxi) -, : 35 5-(4-metoxibensensulfonylamino)bensoat, * I i · 82 116622 4-(2-klor-5-metoxifenoxi)-3-(2-hydroxietoxi)-5-(4-metoxibensensulfonylamino)bensoesyra, 4-(2-klor-5-metoxifenoxi)-3-(2-hydroxietoxi)-5-(4-metoxibensensulfonylamino)-N-fenylbensamid, 5 metyl-3-(benso[1,3]dioxol-5-sulfonylamino)-4-(2-klor- 5-metoxifenoxi)-5-(2-hydroxietoxi)bensoat, 3-(benso[1,3]dioxol-5-sulfonylamino)-4-(2-klor-5-metoxifenoxi)-5-(2-hydroxietoxi)bensoesyra, 3- (benso[1,3]dioxol-5-sulfonylamino)-4-(2-klor-5-10 metoxifenoxi)-5-(2-hydroxietoxi)-N-fenylbensamid, metyl-4-(2-klor-5-metoxifenoxi)-3-(2-hydroxietoxi)- 5-(4-trifluormetylbensensulfonylamino)bensoat, 4- (2-klor-5-metoxifenoxi)-3-(2-hydroxietoxi)-5- (4-trifluormetylbensensulfonylamino)bensoesyra, 15 4-(2-klor-5-metoxifenoxi)-3-(2-hydroxietoxi)-N- fenyl-5-(4-trifluormetylbensensulfonylamino)bensamid, metyl-3-(4-t-butylbensensulfonylamino)-5-(2-hydr-oxietoxi)-4-(3-metoxifenoxi)bensoat, 3- (4-t-butylbensensulfonylamino)-5-(2-hydroxiet-20 oxi)-4-(3-metoxifenoxi)bensoesyra, 4- t-butyl-N-[3-(2-hydroxietoxi)-2-(3-metoxifenoxi ) -5- (morfolin-4-karbonyl)fenyl]bensensulfonamid, ’ 3-(4-t-butylbensensulfonylamino)-5-(2-hydroxiet- h oxi)-4-(3-metoxifenoxi)-N-fenylbensamid, · 25 N-bifenyl-2-yl-3- (4-t-butylbensensulfonylamino)-5- ‘/.j (2-hydroxietoxi)-4-(3-metoxifenoxi)bensamid, 3- (4-t-butylbensensulfonylamino) -5- (2-hydroxiet-oxi) -4- (3-metoxifenoxi) -N- (3-metoxifenyl) bensamid, metyl-2-[3-(4-t-butylbensensulfonylamino)-5-(2-30 hydroxietoxi)-4-(3-metoxifenoxi)bensoylamino]-4-metylpen- tanoat, N-benso[1,3]dioxol-5-yl-3-(4-t-butylbensensulfon-*· ylamino)-5-(2-hydroxietoxi)-4-(3-metoxifenoxi)bensamid, 2- [3- (4-t-butylbensensulfonylamino) -5- (2-hydroxi-35 etoxi)-4-(3-metoxifenoxi)bensoylamino]-4-metylpentansyra, • · 116622 83 metyl-3-(2-hydroxietoxi)-5-(4-metoxibensensulfon-ylamino)-4-(3-metoxifenoxi) bensoat, 3-(2-hydroxietoxi)-5-(4-metoxibensensulfonylami-no)-4-(3-metoxifenoxi)bensoesyra, 5 3-(2-hydroxietoxi-5-(4-metoxibensensulfonylamino)- 4-(3-metoxifenoxi)-N-fenylbensamid, metyl-3-(2-hydroxietoxi)-4-(3-metoxifenoxi)-5-(4-metylsulfanylbensensulfonylamino)bensoat, 3-(2-hydroxietoxi)-4-(3-metoxifenoxi)-5-(4-metyl-10 sulfanylbensensulfonylamino)bensoesyra, 3- (2-hydroxietoxi)-4-(3-metoxifenoxi)-5-(4-metyl-sulfanylbensensulfonylamino)-N-fenylbensamid, 4- t-butyl-N-[3-(2-hydroxietoxi)-2-(2-metoxifenoxi)-fenylbensensulfonamid, 15 4-t-butyl-N-[2-(2-klor-5-metoxifenoxi)-3-(2-hydroxi etoxi) fenyl]bensensulfonamid.
6. Föreningar enligt patentkrav 3, metyl-3-(4-t-butylbensensulfonylamino)-5-(2,3-di-hydroxipropoxi)-4-(3-metoxifenoxi)bensoat, 20 3-(4-t-butylbensensulfonyalmino)-5-(2,3-dihydroxi- propoxi)-4-(3-metoxifenoxi)bensoesyra, .. 3-(4-t-butylbensensulfonylamino)-5-(2,3-dihydroxi- , propoxi)-4-(3-metoxifenoxi)-N-fenylbensamid, metyl-3-(2,3-dihydroxipropoxi)-5-(4-metoxibensen- :·’ 25 sulf onylamino)-4-( 3-metoxifenoxi) -bensoat, 3- (2,3-dihydroxipropoxi)-5- (4-metoxibensensulfon-: '·· ylamino)-4-(3-metoxifenoxi) bensoesyra, 1 3-(2,3-dihydroxipropoxi)-5-( 4-metoxibensensulf on ylamino) -4-(3-metoxifenoxi)-N-fenylbensamid, 30 metyl-3-(2,3-dihydroxipropoxi)-4-(3-metoxifenoxi) - ; » · *·. 5- (4-me tyl sulf any lbens ensulf onylamino) bensoat, 84 116622 3- (4-t-butylbensensulfonylamino)-5-(2,3-dihydroxi-propoxi)-4-(3-metoxifenoxi)-N-(lH-tetrazol-5-yl)bensamid, etyl-4-[3-(2,3-dihydroxipropoxi)-4-(3-metoxifenoxi) -5-(4-metylsulfanylbensensulfonylamino)bensoyl]pipera-5 zin-l-karboxylat, N-[3-(2,3-dihydroxipropoxi)-2-(3-metoxifenoxi)-5-(morfolin-4-karbonyl)-fenyl]-4-metylsulfanylbensensulfon-amid, N-[3-(2-hydroxietoxi)-2-(3-metoxifenoxi)-5-(morfo-10 lin-4-karbonyl)fenyl]4-metylsulfanylbensensulfonamid, 4- t-butyl-N-[5-(cyan-3-(2-hydroxietoxi)-2-(2-met-oxifenoxi)fenyl]bensensulfonamid, 4-t-butyl-N-[3-(2-hydroxietoxi)-2-(2-metoxifen-oxi)-5-(lH-tetrazol-5-yl)fenyl]bensensulfonamid, 15 4-t-butyl-N-[5-(cyan-3-(2-hydroxietoxi)-2-(3-met oxifenoxi )fenyl]bensensulfonamid, 4-tert-butyl-N-[3-(2-hydroxi-etoxi)-2-(3-metoxifenoxi) -5-(lH-tetrazol-5-yl)-fenyl]-bensensulfonamid, 4-t-butyl-N-[5-cyan-3-(2,3-dihydroxipropoxi)-2-(2-20 metoxifenoxi)fenyl]bensensulfonamid, 4-t-butyl-N-[3-(2,3-dihydroxipropoxi)-2-(2-metoxi-fenoxi)-5-(lH-tetrazol-5-yl)fenyl]bensensulfonamid, 4-t-butyl-N-[5-cyan-3-(2,3-dihydroxipropoxi)-2-(3-. *: metoxifenoxi)fenyl]bensensulfonamid, :.· 25 4-t-butyl-N- [3- (2,3-dihydroxipropoxi) -2-(3-metoxi- fenoxi) -5- (lH-tetrazol-5-yl) fenyl]bensensulfonamid.
7. Föreningar enligt patentkrav 2, pyridin-2-yl-karbaminsyra-2-[3-(5-isopropylpyrid-in-2-sulfonylamino)-2-(2-metoxifenoxi)-5-(morfolin-4-kar-: 30 bonyl) fenoxi] etylester, pyridin-2-yl-karbaminsyra-2- [3- (5-isopropylpyrid- » in-2-sulfonylamino)-2-(2-metoxifenoxi)-5-(piperidin-l-kar-' bonyl) fenoxi] etylester, : ·: pyridin-2-yl-karbaminsyra-2-[3-(5-isopropylpyrid- 35 in-2-sulfonylamino)-2-(2-metoxifenoxi)-5-(4-metylpipera-zin-l-karbonyl)fenoxi]etylester, » 116622 85 pyridin-2-yl-karbaminsyra-2-[5-(2,6-dimetylmorfo-lin-4-karbonyl)-3-(5-isopropylpyridin-2-sulfonylamino)-2-(2-metoxifenoxi)fenoxi]etylester, etyl-4-{3-(5-isopropylpyridin-2-sulfonylamino)-4-5 (2-metoxifenoxi)-5-[2-(pyridin-2-ylkarbamoyloxi)etoxi]ben-soyl}piperazin-l-karboxylat, pyridin-2-yl-karbaminsyra-2-[5-(4-formylpiperazin-1-karbonyl)-3-(5-isopropylpyridin-2-sulfonylamino)-2-(2-metoxifenoxi)fenoxi]etylester, 10 metyl-4-(2-klor-5-metoxifenoxi)-3-(5-isopropylpyr- idin-2-sulfonylamino)-5-[2-(pyridin-2-ylkarbamoyloxi)et-oxi]bensoat, pyridin-2-yl-karbaminsyra-2-[2-(2-klor-5-metoxi-fenoxi)-3-(5-isopropylpyridin-2-sulfonylamino)-5-(morfo-15 lin-4-karbonyl)fenoxi]etylester, pyridin-2-yl-karbaminsyra-2-[3-(5-isopropyl-2-pyridylsuIfonylamino)-2-(2-metoxifenoxi)fenoxi]etylester.
8. Föreningar enligt patentkrav 3, metyl-3-(2-hydroxietoxi)-5-(5-isopropylpyridin-2-20 sulfonylamino)-4-(2-metoxifenoxi)bensoat, 3-(2-hydroxietoxi)-5-(5-isopropylpyridin-2-sulfon- ,, ylamino)-4-(2-metoxifenoxi)bensoesyra, 5-isopropylpyridin-2-sulfonsyra-[3-(2-hydroxiet-• oxi)-2-(2-metoxifenoxi)-5-(morfolin-4-karbonyl)fenyl]amid, 25 5-isopropylpyridin-2-sulf onsyra-[ 3-(2-hydroxiet- I · •’.‘•I oxi) -2- (2-metoxifenoxi) -5- (piperidin-l-karbonyl) fenyl] - • ’·. amid, 5-isopropylpyridin-2-sulfonsyra- [3- (2-hydroxiet- t oxi)-2-(2-metoxifenoxi)-5-(4-metylpiperazin-l-karbonyl) -30 fenyl] amid, ' t I * 5-isopropylpyridin-2-sulfonsyra- [5- (2, 6-dimetyl->’ morfolin-4-karbonyl)-3-(2-hydroxietoxi)-2-(2-metoxifen oxi) fenyl] amid, :"· etyl-4-[3-(2-hydroxietoxi)-5-(5-isopropylpyridin- 35 2-sulfonylamino)-4-(2-metoxifenoxi)bensoyl]piperazin-1-karboxylat, 116622 86 5-isopropylpyridin-2-sulfonsyra-[5-(4-formylpipe-razin-l-karbonyl)-3-(2-hydroxietoxi)-2-(2-metoxifenoxi)-fenyl]amid, 3- (2-hydroxietoxi)-5-(5-isopropylpyridin-2-sulfon-5 ylamino)-4-(2-metoxifenoxi)-N-propylbensamid, metyl-4-(2-klor-5-metoxifenoxi)-3-(2-hydroxiet-oxi)-5-(5-isopropylpyridin-2-sulfonylamino)bensoat, 4- (2-klor-5-metoxifenoxi)-3-(2-hydroxietoxi)-5-(5-isopropylpyridin-2-sulfonylamino)bensoesyra, 10 5-isopropyl-pyridin-2-sulfonsyra-[2-(2-klor-5-met- oxifenoxi)-3-(2-hydroxietoxi)-5-morfolin-4-karbonyl)fenyl ]amid, 5- isopropyl-N-[3-(2-hydroxietoxi)-2-(2-metoxifenoxi) fenylpyridinsulfonamid. I 15
9. Förening enligt patentkrav 2, j pyridin-2-yl-karbaminsyra-2-[4-(4-t-butylbensen- sulfonamino)-3-(2-metoxifenoxi)-6-fenylpyridin-2-yloxi]et-ylester.
10. Förening enligt patentkrav 3, 20 4-t-butyl-N-[2-(2-hydroxietoxi)-3-(2-metoxifen oxi) -6-fenylpyrid-4-yl]bensensulfonamid.
, 11. Farmaceutiskt preparat, kännetecknat dä- * rav, att det innehaller en förening enligt nägot av pa-< * * ! tentkraven 1-10 och sedvanliga bärar- och adjuvansämnen. 25
12. Föreningar enligt patentkraven 1-10 för an- :,'‘i vändning som läkemedel. i *
13. Användning av föreningar enligt patentkraven 1 - 10 som aktiva ingredienser för tillverkning av läkemedel » för behandling av sjukdomar som är associerade med endote-30 lin-aktivitet, särskilt blodcirkulationssjukdomar, sasorn t > * » · ,···, hypertension, ischemi, vasospasm och angina pectoris. • ; · t * · i I • ' ‘ * · t 1 * t »
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH383894 | 1994-12-20 | ||
| CH383894 | 1994-12-20 | ||
| CH307995 | 1995-10-31 | ||
| CH307995 | 1995-10-31 | ||
| EP9504762 | 1995-12-04 | ||
| PCT/EP1995/004762 WO1996019455A1 (en) | 1994-12-20 | 1995-12-04 | Aryl- and hetaryl-sulfonamide derivatives, their preparation and their use as endothelin antagonists |
Publications (3)
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| FI972629A0 FI972629A0 (sv) | 1997-06-18 |
| FI972629A FI972629A (sv) | 1997-06-18 |
| FI116622B true FI116622B (sv) | 2006-01-13 |
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| FI972629A FI116622B (sv) | 1994-12-20 | 1997-06-18 | Aryl- och heteroarylsulfonamidderivat, framställning av dem och användning av dem som endotelinantagonister |
Country Status (25)
| Country | Link |
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| US (2) | US5962682A (sv) |
| EP (1) | EP0799206B1 (sv) |
| JP (1) | JP2930731B2 (sv) |
| KR (1) | KR100432843B1 (sv) |
| CN (1) | CN1136192C (sv) |
| AT (1) | ATE223899T1 (sv) |
| AU (1) | AU695255B2 (sv) |
| BR (1) | BR9510533A (sv) |
| CA (1) | CA2208011A1 (sv) |
| CZ (1) | CZ289090B6 (sv) |
| DE (1) | DE69528198T2 (sv) |
| DK (1) | DK0799206T3 (sv) |
| ES (1) | ES2180664T3 (sv) |
| FI (1) | FI116622B (sv) |
| HU (1) | HUT77307A (sv) |
| IL (1) | IL116410A (sv) |
| MA (1) | MA23745A1 (sv) |
| MX (1) | MX9704588A (sv) |
| MY (1) | MY113214A (sv) |
| NO (1) | NO308297B1 (sv) |
| NZ (1) | NZ297774A (sv) |
| PT (1) | PT799206E (sv) |
| RU (1) | RU2163598C2 (sv) |
| TW (1) | TW474920B (sv) |
| WO (1) | WO1996019455A1 (sv) |
Families Citing this family (25)
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| 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 |
| US6613804B2 (en) | 1993-05-20 | 2003-09-02 | Encysive Pharmaceuticals, Inc. | Biphenylsulfonamides 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 |
| 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 |
| AU695255B2 (en) * | 1994-12-20 | 1998-08-13 | F. Hoffmann-La Roche Ag | Aryl- and hetaryl-sulfonamide derivatives, their preparation and their use as endothelin antagonists |
| US5977117A (en) | 1996-01-05 | 1999-11-02 | Texas Biotechnology Corporation | Substituted phenyl compounds and derivatives thereof that modulate the activity of endothelin |
| US5804585A (en) | 1996-04-15 | 1998-09-08 | Texas Biotechnology Corporation | Thieno-pyridine sulfonamides derivatives thereof and related compounds that modulate the activity of endothelin |
| US6653331B2 (en) * | 1996-07-03 | 2003-11-25 | Pharmacia & Upjohn Company | Targeted drug delivery using sulfonamide derivatives |
| EE04156B1 (et) | 1997-04-28 | 2003-10-15 | Texas Biotechnology Corporation | Sulfoonamiidid endoteliini vahendatud haiguste ravimiseks |
| US5783705A (en) | 1997-04-28 | 1998-07-21 | Texas Biotechnology Corporation | Process of preparing alkali metal salys of hydrophobic sulfonamides |
| US6191170B1 (en) * | 1998-01-13 | 2001-02-20 | Tularik Inc. | Benzenesulfonamides and benzamides as therapeutic agents |
| CA2315614C (en) | 1999-07-29 | 2004-11-02 | Pfizer Inc. | Pyrazoles |
| HUP0204168A2 (hu) * | 1999-12-22 | 2003-04-28 | Actelion Pharmaceuticals Ltd. | Butin-diol-származékok, ilyeneket tartalmazó gyógyszerkészítmény és előállítása |
| AU2464301A (en) | 1999-12-31 | 2001-07-16 | Encysive Pharmaceuticals Inc. | Sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US6387915B2 (en) | 2000-05-31 | 2002-05-14 | Pfizer Inc. | Isoxazole-sulfonamide endothelin antagonists |
| US6670362B2 (en) | 2000-09-20 | 2003-12-30 | Pfizer Inc. | Pyridazine endothelin antagonists |
| SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| US7321001B2 (en) * | 2002-12-20 | 2008-01-22 | Amgen Inc. | Asthma and allergic inflammation modulators |
| WO2004074438A2 (en) * | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Ccr8 antagonists |
| WO2004073619A2 (en) * | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Ccr8 antagonists |
| AU2008343924B2 (en) * | 2007-12-19 | 2013-01-17 | Amgen Inc. | Phenyl acetic acid derivatives as inflammation modulators |
| WO2010015623A1 (en) * | 2008-08-05 | 2010-02-11 | Farmaprojects, S. A. | Process for the preparation of endothelin receptor antagonists |
| AR076221A1 (es) | 2009-04-09 | 2011-05-26 | Astrazeneca Ab | Derivado de pirazol [4,5-e] pirimidina y su uso para tratar diabetes y obesidad |
| CN110092743B (zh) * | 2018-01-30 | 2022-03-15 | 中国医学科学院药物研究所 | 苯甲酰胺类化合物及其制备方法、用途和药物组合物 |
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|---|---|---|---|---|
| GB1521932A (en) * | 1976-03-08 | 1978-08-16 | Labaz | Sulphonamide derivatives and process for preparing the same |
| GB8708233D0 (en) * | 1987-04-07 | 1987-05-13 | Smith Kline French Lab | Pharmaceutically active compounds |
| DE69129611T2 (de) * | 1990-08-20 | 1998-12-17 | Eisai Co Ltd | Sulfonamid-Derivate |
| TW270116B (sv) * | 1991-04-25 | 1996-02-11 | Hoffmann La Roche | |
| RU2086544C1 (ru) * | 1991-06-13 | 1997-08-10 | Хоффманн-Ля Рош АГ | Бензолсульфонамидные производные пиримидина или их соли, фармацевтическая композиция для лечения заболеваний, связанных с активностью эндотелина |
| NZ247440A (en) * | 1992-05-06 | 1995-04-27 | Squibb & Sons Inc | Phenyl sulphonamide derivatives, preparation and pharmaceutical compositions thereof |
| TW287160B (sv) * | 1992-12-10 | 1996-10-01 | Hoffmann La Roche | |
| IL111959A (en) * | 1993-12-17 | 2000-07-16 | Tanabe Seiyaku Co | N-(polysubstituted pyrimidin-4-yl) benzenesulfonamide derivatives their preparation and pharmaceutical compositions containing them |
| GB9504854D0 (en) * | 1994-03-31 | 1995-04-26 | Zeneca Ltd | Nitrogen derivatives |
| AU695255B2 (en) * | 1994-12-20 | 1998-08-13 | F. Hoffmann-La Roche Ag | Aryl- and hetaryl-sulfonamide derivatives, their preparation and their use as endothelin antagonists |
-
1995
- 1995-12-04 AU AU43016/96A patent/AU695255B2/en not_active Ceased
- 1995-12-04 CA CA002208011A patent/CA2208011A1/en not_active Abandoned
- 1995-12-04 PT PT95941660T patent/PT799206E/pt unknown
- 1995-12-04 DE DE69528198T patent/DE69528198T2/de not_active Expired - Fee Related
- 1995-12-04 AT AT95941660T patent/ATE223899T1/de not_active IP Right Cessation
- 1995-12-04 WO PCT/EP1995/004762 patent/WO1996019455A1/en active IP Right Grant
- 1995-12-04 US US08/860,985 patent/US5962682A/en not_active Expired - Fee Related
- 1995-12-04 ES ES95941660T patent/ES2180664T3/es not_active Expired - Lifetime
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1997
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1999
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