FI120736B - Substituerade isoxazoler för behandling av inflammation - Google Patents

Substituerade isoxazoler för behandling av inflammation Download PDF

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Publication number
FI120736B
FI120736B FI973292A FI973292A FI120736B FI 120736 B FI120736 B FI 120736B FI 973292 A FI973292 A FI 973292A FI 973292 A FI973292 A FI 973292A FI 120736 B FI120736 B FI 120736B
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Prior art keywords
benzenesulfonamide
phenyl
phenylisoxazol
solution
methyl
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FI973292A
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English (en)
Finnish (fi)
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FI973292A0 (sv
FI973292A (sv
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David L Brown
Richard Mathias Weier
John J Talley
Roland S Rogers
Srinivasan Nagarajan
Jeffery S Carter
Michael A Stealey
Paul W Collins
Karen Seibert
Matthew J Graneto
Xiangdong Xu
Richard Partis
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Searle & Co
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Priority claimed from US08/473,884 external-priority patent/US5633272A/en
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Claims (7)

1. Substituerad isoxazol, som är vald ur en grupp, som bestär av följande: 5 4-[5-metyl-3-fenyl-isoxazol-4yl]bensensulfonamid, 4-[5-etyl-3-fenyl-isoxazol-4-yl]bensensulfonamid, 4-[5-propyl-3-fenyl-isoxazol-4-yl]bensensulfonamid, 4-[5-isopropyl-3-fenyl-isoxazol-4-yl]bensensulfonamid, 10 4-[5-butyl-3-fenyl-isoxazol-4-yl]bensensulfonamid, 4-[5-isobutyl-3-fenyl-isoxazol-4-yl]bensensulfonamid, 4-[5-cyklohexyl-3-fenyl-isoxazol-4-yl]bensensulfonamid, 15 4-[5-neopentyl-3-fenyl”isoxazol-4-yl]bensensulfon amid, 4-[5~cyklohexylmetyl-3-fenyl-isoxazol-4-yl]bensensulfonamid, 4-[5-(4-klorfenyl)metyl-3-fenyl-isoxazol-4-yl]-20 bensensulfonamid, « I 4- [5-difluormetyl-3-fenyl-isoxazol-4-yl] bensensul- i Γ: fonamid, 4- [5-klormetyl-3-fenyl-isoxazol-4-yl] bensensulfon- • · f*·*. amid, • · :·. 25 4-[5-metyl-3-fenyl-isoxazol-4-yl]bensensulfonsyra, ]···. 4- [5-propyl-3-fenyl-isoxazol-4-yl] bensensulfonsyra, * * · 4-[5-metoximetyl-3-fenyl-isoxazol-4-yl]bensensul- fonamid, « · · **[t* 4- [5- (3-hydroxipropyl) -3-fenyl-isoxazol-4-yl] bensen- • · ’···' 30 sulfonamid, *:*·· [4- [4- (aminosulfonyl) fenyl] -3- (3-fluor-4-metoxife- ····! nyl) isoxazol-5-yl]propansyra, ,*, 4- [3™ (3-fluor-4-metoxifenyl) -5-metyl-isoxazol-4- • # t *·**! yl]bensensulfonamid, ····♦ * * 35 4-[3-(4-klorfenyl)-5-metyl-isoxazol-4-yl]bensen sulfonamid, 139 4-[3-(4-fluorfenyl)-5-metyl-isoxazol-4-yl]bensensulfonamid, 4-[3-(3-fluor-4-metylfenyl)-5-metyl-isoxazol~4-yl]-bensensulfonamid, 5 4- [3- (3-klor-4-metylfenyl) -5-metyl-isoxazol-4-yl] - bensensulfonamid, 4-[5-metyl-3-(3-pyridyl)isoxazol-4-yl]bensensulfonamid, 4- [5-metyl-3-(4-pyridyl)isoxazol-4-yl]bensensulfon- 10 amid, 5- metyl-4-[4-(metylsulfonyl)fenyl]pyridyl)-3-fenyl-isoxazol, [3-[3-fluor-4-metoxifenyl]-4-[4-metylsulfonyl)fenyl]-isoxazol-5-yl]attiksyra, 15 3- (3-klor-4-metoxifenyl) -5-metyl-4- [4-metylsulfonyl- fenyl]isoxazol, [4-[4-(aminosulfonyl)fenyl]-3-fenyl-isoxazol-5-yl]attiksyra, 4- [5-hydroximety 1-3--fenyl-isoxazol-4-yl ] bensensul- 20 fonamid, ·*·,· [4- [4- (aminosulfonyl) fenyl] -3-fenyl-isoxazol-5-yl] - φ s karboxylsyra, .·, · 4-[5-hydroxi-3-fenyl-isoxazol-4-yl]bensensulfonamid, • ·· .* 4-[3-metyl-5-fenyl-isoxazol-4-yl]bensensulfonamid, I · I,* 25 4-[3-etyl-5-fenyl-isoxazol-4-yl]bensensulfonamid, ♦ « 4- [3-isopropyl-5-fenyl-isoxazol-4-yl]bensensulfon- *·* * anilid, 4-[5-fenyl-3-propyl-isoxazol-4-yl]bensensulfonamid, ··· V i 4-[3-etyl-5- (4-met yl fenyl) -isoxazol-4-yl] bensensul- ♦ ·· l ϊ 30 fonamid, M· ' 4- [3-butyl-5-fenyl-isoxazol-4-yl] bensensulfonamid, • ft 4- [3-metyl-5- (4-metylfenyl) isoxazol-4-yl] bensensul- • · . fonamid, ft · :.V 4-[5-(4-klorfenyl)-3-metyl-isoxazol-4-yl]bensen- *!*'! 35 sulfonamid, 140 4-[5-(4-fluorfenyl)-3-metyl-isoxazol-4-yl]bensensulfonamid, 3- metyl-5-(4-metylsulfonylfenyyl)-4-fenyl-iso- xazol, 5 4-[3-metyl-4-fenyl-isoxazol-5-yl]bensensulfonamid, 4- [3-metyl-5~(3-klorfenyl)-isoxazol-4-yl]bensensulfonamid, 4-t3-hydroximetyl-5-fenyl-isoxazol-4-yl]bensensulfonamid, 10 4-(4-aminosulfonylfenyl)-5-fenyl-isoxazol-3-ättik- syra, 3- metyl-4-(4-aminosulfonylfenyl)-5-fenyl-isoxazol, 4- [3-[2-(4-klorfenyl)-2-hydroxietyl]-5-fenyl-iso-xazol-4-yl]bensensulfonamid, 15 3-etyl-4-(4-metylsulfonylfenyl)-5-fenyl-isoxazol, 4-[3-etyl-5-(4-fluorfenyl)-isoxazol-4-yl]bensensulfonamid, 4-[3-etyl-5~(3-fluorfenyl)-isoxazol-4-yl]bensensulfonamid, 20 4-[3-etyl-5-(3-metylfenyl)-isoxazol-4-yl]bensen- ·*·,· sulfonamid, • * 4- [3-etyl-5- (2-f luorfenyl) -isoxazol-4-yl] bensen- ; sulfonamid, • ·· [4-[4-(aminosulfonyl)fenyl]-3-fenyl-isoxazol-5- • · j, * 25 yl] -3-metylbutan-l-syra, •#<)* [ [4- [4- (aminosulfonyl) fenyl] -3-fenyl-isoxazol-5- • · · *·* * yl] metoxi] ättiksyra, 4-[4-[4-(aminosulfonyl)fenyl]]-3-fenyl-isoxazol-5- ··· V ! yl]butansyra, :]t*: 30 4-[5-cyan-3-fenyl-isoxazol-4-yl]bensensulfonamid, 4- [5-klor-3-fenyl-isoxazol-4-yl] bensensulfonamid, • · . 4-[5-trifluormetansulfonyloxi-3-fenyl-isoxazol-4- • · , yl]bensensulfonamid, • · !,♦,* 4- [5-metyl-4-fenyl-isoxazol-3-yl] bensensulfonamid, *:**: 35 4-[3- (3, 5-difluorfenyl) -5-metyl-isoxazol-4-yl]ben sensulfonamid, 141 4-[3-(4-bromfenyl)-5-metyl-isoxazol-4-yl]bensen-sulfonamid, 4-[5-difluormetyl-3-(3-fluor-4-metoxifenyl)iso-xazol-4-yl]bensensulfonamid, 5 4-[5-difluormetyl-3-(4-metoxifenyl)isoxazol-4-yl]- bensensulfonamid, 4- [5-difluormetyl-3-(4-metylfenyl)isoxazol-4-yl]-bensensulfonamid, 5- difluormetyl-4-(4-metylsulfonylfenyl)-3-fenyl-10 isoxazol, 4-[3-(3-klorfenyl)-5-metyl-isoxazol-4-yl]bensen-sulfonamid, 4-[3-(3,4-difluorfenyl)-5-metyl-isoxazol-4-yl]bensensulf onamid, 15 metyl-4-[[4-[4-(aminosulfonyl)fenyl]-3-fenyl-iso- xazol-5-yl]metoxi]bensoat, 4-[(4-[4-(aminosulfonyl)fenyl]-3-fenyl-isoxazol-5-yl]metoxi]bensoesyra, 4-[3-fenyl-5-(3,3,3-trifluor-2-oxopropyl)isoxazol-20 4-yl]bensensulfonamid, ·*·.· och farmaceutiskt godtagbara salter därav. • · j*i*.
2. Isoxazol enligt patentkrav 1, vilken är 4-[5- « *·. : metyl-3-fenyl-isoxazol-4-yl]bensensulfonamid eller ett • ·· •·φ/ farmaceutiskt godtagbart salt därav. • s
3. Isoxazol enligt patentkrav 1, vilken är 4-[5- hydroximetyl-3-fenyl-isoxazol-4-yl] bensensulfonamid eller « « · ett farmaceutiskt godtagbart salt därav.
4. Farmaceutisk komposition, kännetecknad av • ·· ·,· * att den omfattar en terapeutiskt effektiv mängd av en sub- ··· ί44>ί 30 stituerad isoxazol enligt nägot av patentkraven 1-3 el- „*.j ler ett farmaceutiskt godtagbart sait därav. * ·
5. Användning av en substituerad isoxazol enligt • · . nägot av patent kraven 1-3 eller ett farmaceutiskt • * *.V godtagbart sait därav för framställning av ett medikament *S**J 35 för behandling av inflammation eller störning, som hänför sig till inflammation. 142
6. Användning enlgt patentkrav 5, känneteck-nad av att störningen, som hänför sig till inflammation, är artrit, smärta eller feber.
7. Förfarande för framställning av 4-[5-metyl-3-5 fenyl-isoxazol-4-yl]bensensulfonamid eller ett farmaceu- tiskt godtagbart sait därav, kännetecknat av att det omfattar följande steg: (i) desoxibensoin omsätts med hydroxylamin för er-hällande av desoxibensoinketooxim, 10 (ii) den i steg (i) erhällna desoxibensoinketooxi- men omsätts först med n-butyllitium och därefter med ät-tiksyraanhydrid, varvid erhälls efter konventionell uppar-betning och rening 3,4-difenyl-4-hydrido-5-hydroxi-5-metyl-isoxazol, 15 (iii) den i steg (ii) erhällna 3,4-difenyl-4- hydrido-5-hydroxi-5-metyl-isoxazolen omsätts med klorsul-fonisyra och efter konventionell snabbavkylning behandlas den organiska fasen med en ammoniumhydroxidlösning, varvid erhälls 4-[5-metyl-3-fenyl-isoxazol-4-yl]bensensulfonamid. • · • 1 · • ·♦ • · • · · • · · • · · • ψ • « • ·· t ·· · * 1 · • I • · ·· • · • M • ·« • · · • 1 t «·· I » » • · · ··· « · • · ··· * • · • · e 1 * · · • · · • · ·
FI973292A 1995-02-13 1997-08-11 Substituerade isoxazoler för behandling av inflammation FI120736B (sv)

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US38768095A 1995-02-13 1995-02-13
US38768095 1995-02-13
US08/473,884 US5633272A (en) 1995-02-13 1995-06-07 Substituted isoxazoles for the treatment of inflammation
US47388495 1995-06-07
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EP0809636A1 (en) 1997-12-03
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NZ302586A (en) 1999-08-30
NL300128I1 (nl) 2003-07-01
CN1214790C (zh) 2005-08-17
JP3267300B2 (ja) 2002-03-18
FI973292A0 (sv) 1997-08-11
NL300128I2 (nl) 2003-09-01
DE69623444D1 (de) 2002-10-10
AU4867196A (en) 1996-09-04
PL321814A1 (en) 1997-12-22
DE10399017I1 (de) 2012-05-16
EP0809636B1 (en) 2002-09-04
CA2212836A1 (en) 1996-08-22
RO119946B1 (ro) 2005-06-30
ES2183935T3 (es) 2003-04-01
US5985902A (en) 1999-11-16
CZ254697A3 (cs) 1998-01-14
US5859257A (en) 1999-01-12
PT809636E (pt) 2002-12-31
FI973292A (sv) 1997-10-10
CZ293211B6 (cs) 2004-03-17
JP2002179656A (ja) 2002-06-26
AU699593B2 (en) 1998-12-10

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