EA017952B1 - ПИРРОЛО[2,3-d]ПИРИДИНЫ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ ТИРОЗИНКИНАЗЫ - Google Patents

Info

Publication number

EA017952B1

EA017952B1 EA201001242A EA201001242A EA017952B1 EA 017952 B1 EA017952 B1 EA 017952B1 EA 201001242 A EA201001242 A EA 201001242A EA 201001242 A EA201001242 A EA 201001242A EA 017952 B1 EA017952 B1 EA 017952B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pyrimidin

pyrrolo

morpholin

compound

phenyl

Prior art date

2008-02-06

Links

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• 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 8
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 3
• RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 876
• 238000000034 method Methods 0.000 claims abstract description 579
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• 230000001404 mediated effect Effects 0.000 claims abstract description 17
• 238000002360 preparation method Methods 0.000 claims abstract description 14
• -1 3,5-dimethylpiperazin-1-yl Chemical group 0.000 claims description 793
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 264
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 234
• 150000001412 amines Chemical class 0.000 claims description 216
• 238000006243 chemical reaction Methods 0.000 claims description 57
• 125000001424 substituent group Chemical group 0.000 claims description 49
• GSENCEDSCQYPIL-UHFFFAOYSA-N morpholin-4-ylmethanone Chemical compound O=[C]N1CCOCC1 GSENCEDSCQYPIL-UHFFFAOYSA-N 0.000 claims description 35
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 30
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 30
• 238000011282 treatment Methods 0.000 claims description 28
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 22
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 22
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
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• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 5
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• VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 2
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
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• KKZWWWBLZNYERB-UHFFFAOYSA-N [2,6-difluoro-4-[2-(pyridin-3-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=NC=CC=4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 KKZWWWBLZNYERB-UHFFFAOYSA-N 0.000 claims 1
• GZVSQRIGTIEXJZ-UHFFFAOYSA-N [2,6-difluoro-4-[2-(pyridin-4-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CN=CC=4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 GZVSQRIGTIEXJZ-UHFFFAOYSA-N 0.000 claims 1
• CGCHXCDIDUYGFK-UHFFFAOYSA-N [2-fluoro-4-[2-(pyridin-3-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=NC=CC=4)=NC=C3C=C2)=CC=C1C(=O)N1CCOCC1 CGCHXCDIDUYGFK-UHFFFAOYSA-N 0.000 claims 1
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• 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
• 125000004212 difluorophenyl group Chemical group 0.000 claims 1
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• 230000008569 process Effects 0.000 abstract description 3
• 238000004128 high performance liquid chromatography Methods 0.000 description 517
• 238000004809 thin layer chromatography Methods 0.000 description 143
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 131
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