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DK2887943T3 - Hidtil ukendte 4,6-disubstituerede aminopyrimidin-derivater - Google Patents

Hidtil ukendte 4,6-disubstituerede aminopyrimidin-derivater Download PDF

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DK2887943T3
DK2887943T3 DK13831626.0T DK13831626T DK2887943T3 DK 2887943 T3 DK2887943 T3 DK 2887943T3 DK 13831626 T DK13831626 T DK 13831626T DK 2887943 T3 DK2887943 T3 DK 2887943T3
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methoxy
pyrimidin
phenyl
ylamino
fluoro
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Franco Lori
György Keri
James Chafouleas
Forni Davide De
Antonio Solinas
László Orfi
Zoltán Greff
Zoltán Varga
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Virostatics Srl
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Claims (2)

1. Forbindelse med formel (I):
(l) hvor X, Y og Z er H, F, eller Cl; Ri er OR, hvor R er hydrogen eller en gruppe valgt fra lige eller forgrenet C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, heterocyclyl, CF3, CCI3, og aryl i position 2, 3 eller 4; R2 er OH, alkoxy, aryloxy, CH2OR (hvor R er H, lineær eller forgrenet aryl, cycloalkyl eller alkyl), CH2NR'R" (hvor R' og R" er uafhængigt H, lineær eller forgrenet aryl, cycloalkyl eller alkyl), CHO, OCOW (hvor W er lineær eller forgrenet aryl eller alkyl eller C-(halogen)3), CONR'R" (hvor R' og R" uafhængigt er H, alkyl, cycloalkyl eller aryl), COOR (hvor R er H, alkyl, cycloalkyl eller aryl), CH2NHSO2R (hvor R er H, alkyl, cycloalkyl eller aryl), Cl, Br, F, CH2-/V-benzimidazol, CONHNR'R" (hvor R' og R" uafhængigt er H, alkyl, cycloalkyl eller aryl), NRCOOR' (hvor R og R' er uafhængigt H, alkyl, cycloalkyl eller aryl), NH2, NR'R" (hvor R' og R" uafhængigt er alkyl, cycloalkyl eller aryl), NHCOR (hvor R er H, alkyl, cycloalkyl eller aryl), nitro, OCH2CH2-heterocyclyl, OCOR (hvor R er H, alkyl, cycloalkyl eller aryl), OCONR'R" (hvor R' og R" er uafhængigt H, alkyl, cycloalkyl eller aryl), OCOOR (hvor R er H, alkyl, cycloalkyl eller aryl), NHCOOCH2C-hal03, NRCONR'R" (hvor R, R' og R" uafhængigt er H, alkyl, cycloalkyl eller aryl), NHSO2R (hvor R er H, alkyl, cycloalkyl eller aryl), NHSC^NR'R" (hvor R' og R" uafhængigt er H, alkyl, cycloalkyl eller aryl),
og R3 er OH, alkoxy, aryloxy, NR'R" (hvor R' og R" er H), NHCOR (hvor R er H, alkyl, cycloalkyl eller aryl), og CONR'R" (hvor R' og R" uafhængigt er H, alkyl, cycloalkyl eller aryl).
2. Forbindelse ifølge krav 1, hvor Ri er OR, hvor R er H, methyl, isopropyl eller ethyl.
3. Forbindelse ifølge krav 1, hvor Ri er 2'-OR, hvor R er H, methyl, ethyl eller isopropyl.
4. Forbindelse ifølge krav 1, hvor Z er H eller F.
5. Forbindelse ifølge krav 1, hvor R2 er valgt fra gruppen bestående af OH, lineær eller forgrenet alkoxy, CH2OR (hvor R er alkyl), NH2, CH2NH2, OCOC(CH3)3, CONH2, Cl, Br, CH2-A/-benzimidazol, NHSO2R (hvor R er alkyl eller aryl) og NHS02NR'R" (hvor R' og R" uafhængigt er H, alkyl, eller aryl), OCH2CH2-heterocyclyl, OCOR (hvor R er H, alkyl, cycloalkyl eller aryl), OCONR'R" (hvor R' og R" er uafhængigt H, alkyl, cycloalkyl eller aryl).
6. Forbindelse ifølge krav 1, hvor R3 er OH, lineær eller forgrenet alkoxy, NR'R" (hvor R' og R" er H), CONR'R" (hvor R' og R" uafhængigt er H, alkyl, cycloalkyl eller aryl).
7. Forbindelse ifølge krav 1, hvor R2 er valgt fra gruppen bestående af OH, lineær eller forgrenet alkoxy, CONH2, OCOC(CH3)3, Cl, CH2-/V-benzimidazol og R3 er valgt fra gruppen bestående af alkoxy.
8. Forbindelse ifølge krav 1, hvor X, Y og Z er H eller F, R2 er lineær eller forgrenet alkoxy, CONH2, OCOC(CH3)3, Cl, CH2-/V-benzimidazol og R3 er alkoxy.
9. Forbindelse ifølge krav 1, hvor X, Y og Z er H eller F, Ri er methoxy eller ethoxy, R2 er lineær eller forgrenet alkoxy, CONH2, Cl, Br, CH2-/V-benzimidazol og R3 er alkoxy.
10. Forbindelse ifølge krav 1, hvor X og Y er 4'-F, 5'-F eller H og Z er 2'-F eller H, Ri er 2'-0R, hvor R er H, methyl, ethyl, eller isopropyl, R2 er lineær eller forgrenet alkoxy, CONH2, Cl, Br, CH2-/V-benzimidazol og R3 er OR' (hvor R' er alkyl).
11. Farmaceutisk sammensætning omfattende en farmaceutisk acceptabel excipiens, fortynder eller bærer og en terapeutisk effektiv mængde af en forbindelse ifølge et hvilket som helst af kravene 1 til 10.
12. Forbindelse ifølge et hvilket som helst af kravene 1 til 10 valgt fra:
2-Methoxy-N4-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-benzen-l,4-diamin (Eksempel 59); Methyl 2-Methoxy-5-(6-(2-methoxy-phenyl)-pyrimidin-4-ylamino]-benzoat (Eksempel 30); N1-[6-(4-Fluor-2-methoxy-phenyl)-pyrimidin-4-yl]-4-methoxybenzen-l,3-diamin (Eksempel 64);
4-Fluor-6-methoxy-N3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-benzen-l,3-diamin (Eksempel 92);
4- Fluor-5-[6-(5-fluor-2-methoxy-phenyl)-pyrimidin-4-ylamino]-2-methoxy-benzamid (Eksempel 144); 2-methoxy-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)phenylpivalat (Eksempel 26); 5- [6-(4-Fluor-2-methoxy-phenyl)-pyrimidin-4-ylamino]-2-methoxy-phenol (Eksempel 123); /V-(3-(benzyloxy)-4-methoxyphenyl)-6-(2-methoxyphenyl)-pyrimidin-4-amin (Eksempel 36); A/-(3-fluor-4-methoxyphenyl)-6-(2-methoxyphenyl)pyrimidin-4-amin (Eksempel 22); 2-methoxy-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)-phenol (Eksempel 32); 4-methoxy-N1-(6-(2-methoxyphenyl)pyrimidin-4-yl)benzen-l,3-diamin (Eksempel 41); 2-methoxy-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)benzamid (Eksempel 45); {2-Methoxy-5-[6-(2-methoxy-phenyl)-pyrimidin-4-ylamino]-phenyl>-carbaminsyre-methylester (Eksempel 51); (2-methoxy-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)-phenyl)(methylsulfamoyl)amin (Eksempel 10); /V-benzyl-2-methoxy-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)benzamid (Eksempel 23); (2-methoxy-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)-phenyl)methanol (Eksempel 24); 2-methoxy-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)-/V-methylbenzamid (Eksempel 25); /V-(4-methoxy-3-nitrophenyl)-6-(2-methoxyphenyl)pyrimidin-4-amin (Eksempel 11); N1-[6-(2-Isopropoxy-phenyl)-pyrimidin-4-yl]-4-methoxybenzen-l,3-diamin (Eksempel 79); /V-(3-((dimethylamino)methyl)-4-methoxyphenyl)-6-(2-methoxyphenyl)pyrimidin-4-amin (Eksempel 35); /V-(4-methoxy-3-((phenylamino)methyl)phenyl)-6-(2-methoxyphenyl)pyrimidin-4-amin (Eksempel 34); 2-(2-methoxy-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)-benzyl)isoindolin-l,3-dion (Eksempel 3);
4- Fluor-5-[6-(4-fluor-2-methoxy-phenyl)-pyrimidin-4-ylamino]-2-methoxy-benzamid (Eksempel 146); 5- [6-(4-Fluor-2-methoxy-phenyl)-pyrimidin-4-ylamino]-2-methoxy-benzamid (Eksempel 128);
4- Fluor-2-methoxy-5-[6-(2-methoxy-phenyl)-pyrimidin-4-ylamino]-benzamid (Eksempel 143); 5- [6-(2-Ethoxy-phenyl)-pyrimidin-4-ylamino]-4-fluor-2-methoxy-benzamid (Eksempel 145); 5-[6-(2-Ethoxy-4-fluor-phenyl)-pyrimidin-4-ylamino]-4-fluor-2-methoxy-benzamid (Eksempel 147); 4-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)-2-nitrophenol (Eksempel 12); N-(3-((benzylamino)methyl)-4-methoxyphenyl)-6-(2-methoxyphenyl)pyrimidin-4-amin (Eksempel 1); N-(3-(aminomethyl)-4-methoxyphenyl)-6-(2-methoxyphenyl)-pyrimidin-4-amin (Eksempel 43);
3-Fluor-5-[6-(4-fluor-2-methoxy-phenyl)-pyrimidin-4-ylamino]-2-methoxy-benzamid (Eksempel 138); og
3-Fluor-5-[6-(5-fluor-2-methoxy-phenyl)-pyrimidin-4-ylamino]-2-methoxy-benzamid (Eksempel 140).
13. Forbindelse valgt fra
2-Dimethylamino-5-[6-(4-fluor-2-methoxy-phenyl)-pyrimidin-4-ylamino]-benzamid (Eksempel 113); 2-(2-Chlor-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)benzyl)isoindolin-l,3-dion (Eksempel 20); ethyl 2-chlor-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)benzoat (Eksempel 14);
2-Fluor-N4-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-Nl,Nl-dimethyl-benzen-l,4-diamin (Eksempel 106);
2-Dimethylamino-5-[6-(2-methoxy-phenyl)-pyrimidin-4-ylamino]-phenol (Eksempel 108);
2-Dimethylamino-5-[6-(2-methoxy-phenyl)-pyrimidin-4-ylamino]-benzamid (Eksempel 109); ethyl5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)-2-morpholinobenzoat (Eksempel 18); 2-chlor-5-(6-(2-methoxyphenyl)pyrimidin-4-ylamino)benzamid (Eksempel 44); og N-(3-((lH-benzo[d]imidazol-l-yl)methyl)-4-(4-methylpiperazin-l-yl)phenyl)-6-(2-methoxyphenyl)pyrimidin-4-amin (Eksempel 2).
DK13831626.0T 2012-08-23 2013-08-23 Hidtil ukendte 4,6-disubstituerede aminopyrimidin-derivater DK2887943T3 (da)

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US201261692641P 2012-08-23 2012-08-23
PCT/US2013/056347 WO2014031937A1 (en) 2012-08-23 2013-08-23 Novel 4,6-disubstituted aminopyrimidine derivatives

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EP (1) EP2887943B1 (da)
JP (2) JP6639231B2 (da)
KR (1) KR102209229B1 (da)
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CN109761909B (zh) * 2019-01-25 2022-08-26 中国药科大学 N-(4-(嘧啶-4-氨基)苯基)磺酰胺类抑制剂或其可药用的盐、其制备方法及用途
IT201900004737A1 (it) 2019-03-29 2020-09-29 Virostatics Srl Composti aventi attività enzimatica anti-CDK4/6 e anti-CDK9 per l’inibizione della proliferazione del cancro e relativi metodi di screening per la loro identificazione.
CN111269215B (zh) * 2020-04-01 2021-10-26 中科利健制药(广州)有限公司 含氮杂环有机化合物及其制备方法和应用
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