DK1997811T3 - Indazol-, benzoxazol- og pyrozolopyridinderivater som P38-kinasehæmmere - Google Patents
Indazol-, benzoxazol- og pyrozolopyridinderivater som P38-kinasehæmmere Download PDFInfo
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- DK1997811T3 DK1997811T3 DK08164861.0T DK08164861T DK1997811T3 DK 1997811 T3 DK1997811 T3 DK 1997811T3 DK 08164861 T DK08164861 T DK 08164861T DK 1997811 T3 DK1997811 T3 DK 1997811T3
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Claims (13)
1
1. Forbindelse, der indbefatter opløste enantiomerer, diastereomerer, solvater og farmaceutisk acceptable salte deraf, hvilken forbindelse har formlen XVII: 5 r T OJL Rx-Q-Ry <o(oJ XVII hvor Y er O, NR2; 10 WerCR3; R3 er H, NH2, F, Cl, methyl eller substitueret methyl; R2 er H, OH, en aminbeskyttelsesgruppe, Zn-NRaRb, Zn-NRa(C=0)Rb, zn-S02Ra, Zn-SORa, Zn-SRa, Zn-ORa, Zn-(C=0)Ra, Zn-(C=0)0Ra, Zn-0-(C=0)Ra, alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, 15 heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, hvor cycloalkyl er mættet eller delvist umættet, Zn-heterocycloalkyl, hvor heterocycloalkyl er mættet eller delvist umættet, eller Zn-Ar1, hvor alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-heterocycloalkyl og Zn-Ar1 kan være substitueret eller ikke-2 0 substitueret; Ar1 er aryl eller heteroaryl, der begge kan være substitueret eller ikke-substitueret; Ra og Rb uafhængigt er H, OH, en aminbeskyttelsesgruppe, en alkoholbeskyttelsesgruppe, en syrebeskyttelsesgruppe, en 2 5 svovlbeskyttelsesgruppe, alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, hvor cycloalkyl er mættet eller delvist umættet, Zn-heterocycloalkyl, hvor heterocycloalkyl er mættet eller delvist umættet, eller Zn-Ar1, hvor alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-heterocycloalkyl og Zn-Ar1 kan være substitueret eller ikke-substitueret, eller Ra og Rb sammen med de atomer, hvortil de begge er bundet, danner en mættet eller delvist umættet heterocyklusring med 1 eller flere heteroatomer i ringen, hvor heterocyklussen kan være substitueret eller ikke-substitueret, og hvor heterocyklussen kan være kondenseret til en aromatisk ring; Z er alkylen, der har fra 1 til 4 carboner, eller alkenylen eller alkynylen, der hver har fra 2 til 4 carboner, hvor alkylen, alkenylen eller alkynylen kan være substitueret eller ikke-substitueret; n er 0 eller 1; Uer CRCeller N; V er CRC eller N; Rc er H, F, Cl, methyl eller substitueret methyl; X er O, S, SO, S02, NR5, C=0, CH2, CH2Zn-OH eller C=NORd; R5 er H, methyl eller substitueret methyl; Rd er H, P03H2, S03H2, alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, hvor cycloalkyl er mættet eller delvist umættet, Zn-heterocycloalkyl, hvor heterocycloalkyl er mættet eller delvist umættet, eller Zn-Ar1, hvor alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-heterocycloalkyl og Zn-Ar1 kan være substitueret eller ikke-substitueret; G, K, J, og T uafhængigt er N eller CRZ, forudsat, når en hvilken som helst af G, K, J og T er N, at det totale antal af G, K, J, eller T, der er N, ikke overstiger 2; Rz er H, F, Cl, Br, CF3, OR6, SR6, lavere alkyl (CrC4), CN, eller NR6R7; R6 og R7 uafhængigt er H, CF3, lavere alkyl (CrC4) eller lavere heteroalkyl (CrC4); Q er -NR8CONH-, -NHCO-, -NR8S02NH-, -NHS02-, -CONR11-; R8 er H eller (CrC4) alkyl; R11 er H eller (CrC4) alkyl; Rx er -(CR9R10)m-, -O(CR9R10)m-, NH(CR9R10)m- eller -S(CR9R10)m- forudsat at Q er -CONR11-, når Rx er -O(CR9R10)m_, -NH(CR9R10)m eller -S(CR9R10)m-; R9 og R10 uafhængigt er H eller lavere alkyl, eller R9 og R10 sammen med de atomer, hvortil de begge er bundet, danner en cycloalkylring, der kan være mættet eller delvist umættet; m er 1-3; Ry er H, P03H, en aminbeskyttelsesgruppe, en oxygenbeskyttelsesgruppe, alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, hvor cycloalkyl er mættet eller delvist umættet, Zn-heterocycloalkyl, hvor heterocycloalkyl er mættet eller delvist umættet, eller Zn-Ar2, hvor alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-Ar2 og Zn-heterocycloalkyl kan være substitueret eller ikke-substitueret; Ar2 er aryl eller heteroaryl, der begge kan være substitueret eller ikke-substitueret, hvor substitutionen kan være 1-3 substituenter uafhængigt udvalgt fra F, Cl, Br, CF3, CN, alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, -OR12, -SR12, -S02R12, -S02NR13R12, NR13S02R12, Zn-cycloalkyl, hvor cycloalkyl er mættet eller delvist umættet, Zn-heterocycloalkyl, hvor heterocycloalkyl er mættet eller delvist umættet, eller Zn-Ar1, hvor alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-heterocycloalkyl og Zn-Ar1 kan være substitueret eller ikke-substitueret; R12 og R13 uafhængigt er H, alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, Zn-cycloalkyl, hvor cycloalkyl er mættet eller delvist umættet, Zn-heterocycloalkyl, hvor heterocycloalkyl er mættet eller delvist umættet, eller Zn-Ar1, hvor alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-heterocycloalkyl og Zn-Ar1 kan være substitueret eller ikke-substitueret; Hvor, når Ar2 er substitueret med -S02NR13R12, R12 og R13 kan danne en cycloalkylring eller heterocycloalkylring, der kan være substitueret eller ikke-substitueret, hvor substitutionen kan være substituenter udvalgt fra alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, hvor cycloalkyl er mættet eller delvist umættet, -COR12, -S02R12, Zn-heterocycloalkyl, hvor heterocycloalkyl er mættet eller delvist umættet, eller Zn-Ar1, hvor alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-heterocycloalkyl og Zn-Ar1 kan være substitueret eller ikke-substitueret; hvor, når Q er -CONR11, Ry i kombination med R11 endvidere er en cycloalkylring eller heterocycloalkylring, der kan være substitueret eller ikke-substitueret med grupper udvalgt fra alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, hvor cycloalkyl er mættet eller delvist umættet, Zn-heterocycloalkyl, hvor heterocycloalkyl er mættet eller delvist umættet, Zn-Ar1, -COR14, eller -S02R14, hvor alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-heterocycloalkyl, Zn-Ar1, -COR14, og -S02R14 kan være substitueret eller ikke-substitueret; og R14 er alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, Zn-cycloalkyl, hvor cycloalkyl er mættet eller delvist umættet, Zn-heterocycloalkyl, hvor heterocycloalkyl er mættet eller delvist umættet, eller Zn-Ar1, hvor alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-heterocycloalkyl og Zn-Ar1 kan være substitueret eller ikke-substitueret, og hvor hver gruppes substituent(er) er udvalgt blandt: halo, alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl, Zn-heterocycloalkyl, Zn-OR, Zn-N02, Zn-CN, Zn-C02R, Zn-(C=0)R, Zn-0(0=0)R, Zn-0-alkyl, Zn-OAr, Zn-SH, Zn-SR, Zn-SOR, Zn-S02R, Zn-S-Ar, Zn-SOAr, Zn-S02Ar, aryl, heteroaryl, Zn-Ar, Zn-(C=0)NR’R”, Zn-NR’R”, Zn-NR(C=0)R, Zn-S02NR’R”, P03H2, S03H2, aminbeskyttelsesgrupper, alkoholbeskyttelsesgrupper, svovlbeskyttelsesgrupper eller syrebeskyttelsesgrupper, hvor: Z er alkylen der har fra 1 til 4 carboner, eller alkenylen eller alkynylen, der hver har fra 2 til 4 carboner, n er nul eller 1, R, R’ og R” er alkyl, allyl, alkenyl, alkynyl, heteroalkyl, heteroallyl, heteroalkenyl, heteroalkynyl, alkoxy, heteroalkoxy, Zn-cycloalkyl eller Zn-heterocycloalkyl, og Ar er aryl eller heteroaryl.
2. Forbindelse ifølge krav 1, hvor W er CH og Y er NR2.
3. Forbindelse ifølge krav 1, hvor G, J, K og T er CRZ.
4. Forbindelse ifølge krav 1, hvor X er NH, S eller O.
5. Forbindelse ifølge krav 1, hvor Rx er CH2 og Q er -NHCO-. yv"'\ y— -t | S ' I ^ 0
6. Forbindelse ifølge krav 5, hvor Ry er isopropyl eller ^—* .
7. Forbindelse ifølge krav 1, hvor Rx er CH2 og Q er -NR8CONH-,
8. Forbindelse ifølge krav 7, hvor Ry er
9. Forbindelse ifølge et hvilket som helst af kravene 1 til 8, hvilken forbindelse er udvalgt fra gruppen bestående af: 1 -(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3[2-(1 -methyl-1 H-indazol-5-yloxy)-pyridin-3-ylmethyl]-urea, 1-[5-cyclopropyl-2-(4-trifluormethylphenyl)-2H-pyrazol-3yl]-3-(5-fluor-2-(1 -methyl-1 H-indazol-5-ylamino)-benzyl]-urea, 1 -(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[2-(1 -cyclobutylmethyl-1 H-indazol-5-ylamino)-5-fluorbenzyl]-urea, 1 -(5-tert-butyl-2-p-chlorphenyl-2H-pyrazol-3-yl)-3[2-(1 -methyl-1 H-indazo-5-ylsulfanyl)-5-fluorbenzyl]-urea, 1 -(5-tert-butyl-2-methy1 -2H-pyrazol-3-yl)-3-{2-[1 -(3-isopropylamino-propyl)-1H-indazol-5-ylamino]-benzyl}-urea, 1 -(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[5-fluor-2-(1 -methyl-1 H-indazol-5-yloxy)-benzyl]urea, 1 [5-tert-butyl-2-(4-chlorphenyl)-2H-pyrazol-3-yl]-3-[5-fluor-2-(1 -methyl-1 H-indazol-5-yloxy)-benzyl]urea, 3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-1 -[5-fluor-2-(1 -methyl-1 H-indazol-5-yloxy)-benzyl]-1-methylurea, 1 -(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[5-fluor-2-(1 -methyl-1 H-indazol-5-yloxy)-benzyl]-1-methylurea, 1 -(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[5-fluor-2-(1 -methyl-1 H-pyrazol[3,4-c]pyridin-5-yloxy)-benzyl]-urea, 2-(5-{2-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl}-ureidomethyl]-4- fluorphenoxy)-indazol-1-yl)-N,N-dimethylacetamid, 1 -(5-tert-butyl-isoxazol-3-yl)-3[5-fluor-2-(1 -isobutyl-1 H-indazol-5-yloxy)-benzyl]-urea, 1 -(3-tert-butyl-isoxazol-5-yl)-3-{5-fluor-2[1 -(2-piperazin-1 -yl-ethyl)-1 H-indazol-5-yloxy]-benzyl}urea, 1 -(3-tert-butyl-isoxazol-5-yl)-3-{2[1 -(2-dimethylaminoethyl)-1 H-indazol-5-yloxyl-5-fluor-benzyl)-urea, 1 -(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3-{5-fluor-2-[1 -(2-hydroxy-2-methylpropyl)-1 H-indazol-5-yloxy]-benzyl}-urea og et farmaceutisk acceptabelt salt deraf.
10. Sammensætning omfattende en forbindelse ifølge krav 1 og et farmaceutisk acceptabelt bærestof.
11. Forbindelse ifølge et hvilket som helst af kravene 1 til 9 til anvendelse i terapi.
12. Forbindelse ifølge et hvilket som helst af kravene 1 til 9 til anvendelse ved behandling eller forebyggelse af en p-38-medieret tilstand.
13. Forbindelse ifølge krav 12, hvor den p-38-medierede tilstand er en inflammatorisk sygdom, autoimmun sygdom, destruktiv knogleforstyrrelse, proliferativ knogleforstyrrelse, infektionssygdom, virussygdom eller neurodegenerativ sygdom.
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US10/378,164 US7135575B2 (en) | 2003-03-03 | 2003-03-03 | P38 inhibitors and methods of use thereof |
US10/688,849 US20040180896A1 (en) | 2003-03-03 | 2003-10-15 | P38 inhibitors and methods of use thereof |
EP04714621A EP1606283B1 (en) | 2003-03-03 | 2004-02-25 | P38 inhibitors and methods of use thereof |
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DK08164861.0T DK1997811T3 (da) | 2003-03-03 | 2004-02-25 | Indazol-, benzoxazol- og pyrozolopyridinderivater som P38-kinasehæmmere |
DK08166014.4T DK2039685T3 (da) | 2003-03-03 | 2004-02-25 | Heterobicycliske forbindelser som P38-inhibitorer |
DK04714621T DK1606283T3 (da) | 2003-03-03 | 2004-02-25 | P38-inhibitorer og fremgangsmåder til anvendelse deraf |
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