KR100669578B1 - 2-(피리딘-2-일아미노)-피리도[2,3-ｄ]피리미딘-7-온 - Google Patents

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Publication number

KR100669578B1

KR100669578B1 KR1020047011276A KR20047011276A KR100669578B1 KR 100669578 B1 KR100669578 B1 KR 100669578B1 KR 1020047011276 A KR1020047011276 A KR 1020047011276A KR 20047011276 A KR20047011276 A KR 20047011276A KR 100669578 B1 KR100669578 B1 KR 100669578B1

Authority

KR

South Korea

Prior art keywords

pyrido

cyclopentyl

ylamino

pyridin

pyrimidin

Prior art date

2002-01-22

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• DDZFNEVGSZKHPR-UHFFFAOYSA-N 2-(pyridin-2-ylamino)-6h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C2=NC(=O)CC=C2C=NC=1NC1=CC=CC=N1 DDZFNEVGSZKHPR-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 119
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
• 201000010099 disease Diseases 0.000 claims abstract description 27
• -1 aryl-C 1 -C 6 alkyl Chemical group 0.000 claims description 159
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 81
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
• 229910052757 nitrogen Chemical group 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 45
• 206010028980 Neoplasm Diseases 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• 201000011510 cancer Diseases 0.000 claims description 31
• 229910052760 oxygen Inorganic materials 0.000 claims description 31
• 238000000034 method Methods 0.000 claims description 29
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001301 oxygen Substances 0.000 claims description 25
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
• 239000011593 sulfur Chemical group 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 150000002431 hydrogen Chemical class 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 210000004027 cell Anatomy 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
• 125000002837 carbocyclic group Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 150000002825 nitriles Chemical class 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 9
• 150000001721 carbon Chemical group 0.000 claims description 9
• QZDZRDATWGQUSE-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-(pyridin-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3N=CC=CC=3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 QZDZRDATWGQUSE-UHFFFAOYSA-N 0.000 claims description 8
• RNSUPAGDKUJPOH-UHFFFAOYSA-N 2-[[5-[bis(2-methoxyethyl)amino]pyridin-2-yl]amino]-6-bromo-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CC(N(CCOC)CCOC)=CC=C1NC1=NC=C(C(C)=C(Br)C(=O)N2C3CCCC3)C2=N1 RNSUPAGDKUJPOH-UHFFFAOYSA-N 0.000 claims description 7
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 7
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 7
• 208000031481 Pathologic Constriction Diseases 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• 230000036262 stenosis Effects 0.000 claims description 7
• 208000037804 stenosis Diseases 0.000 claims description 7
• RNDSKWSXUGROBX-UHFFFAOYSA-N 6-acetyl-2-[[5-[bis(2-methoxyethyl)amino]pyridin-2-yl]amino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CC(N(CCOC)CCOC)=CC=C1NC1=NC=C(C(C)=C(C(C)=O)C(=O)N2C3CCCC3)C2=N1 RNDSKWSXUGROBX-UHFFFAOYSA-N 0.000 claims description 6
• CHQDKNRHNGRBFW-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[(5-morpholin-4-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CCOCC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 CHQDKNRHNGRBFW-UHFFFAOYSA-N 0.000 claims description 6
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
• 206010009944 Colon cancer Diseases 0.000 claims description 6
• 208000003445 Mouth Neoplasms Diseases 0.000 claims description 6
• 208000009565 Pharyngeal Neoplasms Diseases 0.000 claims description 6
• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 6
• 208000015181 infectious disease Diseases 0.000 claims description 6
• 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims description 6
• 206010038038 rectal cancer Diseases 0.000 claims description 6
• 201000001275 rectum cancer Diseases 0.000 claims description 6
• LPIVOYTWXHJHMK-UHFFFAOYSA-N tert-butyl 4-[6-[(6-bromo-8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]pyridin-3-yl]-2,2-dimethylpiperazine-1-carboxylate Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CC(C)(C)N(C(=O)OC(C)(C)C)CC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 LPIVOYTWXHJHMK-UHFFFAOYSA-N 0.000 claims description 6
• YZPPSKASXKNBBK-UHFFFAOYSA-N tert-butyl 4-[6-[(6-bromo-8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]pyridin-3-yl]-2,6-dimethylpiperazine-1-carboxylate Chemical compound C1C(C)N(C(=O)OC(C)(C)C)C(C)CN1C(C=N1)=CC=C1NC1=NC=C(C(C)=C(Br)C(=O)N2C3CCCC3)C2=N1 YZPPSKASXKNBBK-UHFFFAOYSA-N 0.000 claims description 6
• ZPESXJSLZIYESZ-UHFFFAOYSA-N tert-butyl 4-[6-[[8-cyclopentyl-6-(1-ethoxyethenyl)-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]-2,2-dimethylpiperazine-1-carboxylate Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=C)OCC)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCN(C(=O)OC(C)(C)C)C(C)(C)C1 ZPESXJSLZIYESZ-UHFFFAOYSA-N 0.000 claims description 6
• ZZIARAVQPQVMHU-UHFFFAOYSA-N tert-butyl 4-[6-[[8-cyclopentyl-6-(2-methoxyethoxymethyl)-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylate Chemical compound N1=C2N(C3CCCC3)C(=O)C(COCCOC)=CC2=CN=C1NC(N=C1)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 ZZIARAVQPQVMHU-UHFFFAOYSA-N 0.000 claims description 6
• HOSSGPJLIMSTBP-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-5-methyl-2-[(5-piperidin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCCCC1 HOSSGPJLIMSTBP-UHFFFAOYSA-N 0.000 claims description 5
• PBSZUBKCQUPZFE-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-5-methyl-2-[[5-(4-methylpiperazin-1-yl)pyridin-2-yl]amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=N1)=CC=C1NC1=NC=C(C(C)=C(C(C)=O)C(=O)N2C3CCCC3)C2=N1 PBSZUBKCQUPZFE-UHFFFAOYSA-N 0.000 claims description 5
• LNWBFIONGCLDNM-UHFFFAOYSA-N 6-amino-8-cyclopentyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.N1=C2N(C3CCCC3)C(=O)C(N)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 LNWBFIONGCLDNM-UHFFFAOYSA-N 0.000 claims description 5
• NTXLAYBXFAYPPZ-UHFFFAOYSA-N 6-benzyl-8-cyclopentyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.C=1C2=CN=C(NC=3N=CC(=CC=3)N3CCNCC3)N=C2N(C2CCCC2)C(=O)C=1CC1=CC=CC=C1 NTXLAYBXFAYPPZ-UHFFFAOYSA-N 0.000 claims description 5
• JPJBKLUESOYNLD-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-(pyridin-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(Br)=CC2=CN=C1NC1=CC=CC=N1 JPJBKLUESOYNLD-UHFFFAOYSA-N 0.000 claims description 5
• NCQPMBZTTMDTHE-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.N1=C2N(C3CCCC3)C(=O)C(Br)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 NCQPMBZTTMDTHE-UHFFFAOYSA-N 0.000 claims description 5
• POJKMTSCTDNKEZ-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(C)=NC=C2C=C(Br)C(=O)N1C1CCCC1 POJKMTSCTDNKEZ-UHFFFAOYSA-N 0.000 claims description 5
• DZCHDINWDGTTBZ-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 DZCHDINWDGTTBZ-UHFFFAOYSA-N 0.000 claims description 5
• DRPKQYAJUXMOND-UHFFFAOYSA-N 8-cyclopentyl-2-(pyridin-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=N1 DRPKQYAJUXMOND-UHFFFAOYSA-N 0.000 claims description 5
• DHBOSQDNEFMAIS-UHFFFAOYSA-N 8-cyclopentyl-2-[[5-(2,6-dimethylmorpholin-4-yl)pyridin-2-yl]amino]-6-(1-ethoxyethenyl)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=C)OCC)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CC(C)OC(C)C1 DHBOSQDNEFMAIS-UHFFFAOYSA-N 0.000 claims description 5
• GRCVSTKNCMOLAR-UHFFFAOYSA-N 8-cyclopentyl-6-(1-ethoxyethenyl)-5-methyl-2-[(5-morpholin-4-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=C)OCC)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCOCC1 GRCVSTKNCMOLAR-UHFFFAOYSA-N 0.000 claims description 5
• ZJZFBJFOMYHRTE-UHFFFAOYSA-N 8-cyclopentyl-6-(2-methylpropoxy)-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.N1=C2N(C3CCCC3)C(=O)C(OCC(C)C)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 ZJZFBJFOMYHRTE-UHFFFAOYSA-N 0.000 claims description 5
• PBWYPNJVIZCRDR-UHFFFAOYSA-N 8-cyclopentyl-6-(hydroxymethyl)-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.N1=C2N(C3CCCC3)C(=O)C(CO)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 PBWYPNJVIZCRDR-UHFFFAOYSA-N 0.000 claims description 5
• BWQCRPSZHRGYAS-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.N1=C2N(C3CCCC3)C(=O)C(F)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 BWQCRPSZHRGYAS-UHFFFAOYSA-N 0.000 claims description 5
• UQKVGYXAXJDYHU-UHFFFAOYSA-N 8-cyclopentyl-6-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.N1=C2N(C3CCCC3)C(=O)C(C)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 UQKVGYXAXJDYHU-UHFFFAOYSA-N 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• 206010034811 Pharyngeal cancer Diseases 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 5
• 229960001171 acetohydroxamic acid Drugs 0.000 claims description 5
• 150000001450 anions Chemical class 0.000 claims description 5
• OIBIBKOKHRSMAB-UHFFFAOYSA-N ethyl 8-cyclopentyl-5-methyl-2-[[5-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]pyridin-2-yl]amino]-7-oxopyrido[2,3-d]pyrimidine-6-carboxylate Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)OCC)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 OIBIBKOKHRSMAB-UHFFFAOYSA-N 0.000 claims description 5
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 201000005202 lung cancer Diseases 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• AHJRHEGDXFFMBM-UHFFFAOYSA-N palbociclib Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 AHJRHEGDXFFMBM-UHFFFAOYSA-N 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• HQNWVBFZDVJCAW-UHFFFAOYSA-N tert-butyl 4-[6-[(6-bromo-8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]pyridin-3-yl]azepane-1-carboxylate Chemical compound C12=NC(NC=3N=CC(=CC=3)C3CCN(CCC3)C(=O)OC(C)(C)C)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 HQNWVBFZDVJCAW-UHFFFAOYSA-N 0.000 claims description 5
• ZFQGPCBCGFJESP-UHFFFAOYSA-N tert-butyl 4-[6-[(8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]pyridin-3-yl]piperazine-1-carboxylate Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CCN(CC3)C(=O)OC(C)(C)C)=NC=C2C(C)=CC(=O)N1C1CCCC1 ZFQGPCBCGFJESP-UHFFFAOYSA-N 0.000 claims description 5
• NDGREAQECAQCJB-UHFFFAOYSA-N tert-butyl 4-[6-[[8-cyclopentyl-6-(2-ethoxyethoxy)-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylate Chemical compound N1=C2N(C3CCCC3)C(=O)C(OCCOCC)=CC2=CN=C1NC(N=C1)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 NDGREAQECAQCJB-UHFFFAOYSA-N 0.000 claims description 5
• VOEKVKVNSXNIOW-UHFFFAOYSA-N tert-butyl 4-[6-[[8-cyclopentyl-6-(2-ethoxyethyl)-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylate Chemical compound N1=C2N(C3CCCC3)C(=O)C(CCOCC)=CC2=CN=C1NC(N=C1)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 VOEKVKVNSXNIOW-UHFFFAOYSA-N 0.000 claims description 5
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
• NVURUIMJTOVZJR-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-2-[[5-(2,6-dimethylmorpholin-4-yl)pyridin-2-yl]amino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)OC(C)CN1C(C=N1)=CC=C1NC1=NC=C(C(C)=C(C(C)=O)C(=O)N2C3CCCC3)C2=N1 NVURUIMJTOVZJR-UHFFFAOYSA-N 0.000 claims description 4
• JDAYPETZCPTRRN-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-2-[[5-(2-methoxyethoxy)pyridin-2-yl]amino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CC(OCCOC)=CC=C1NC1=NC=C(C(C)=C(C(C)=O)C(=O)N2C3CCCC3)C2=N1 JDAYPETZCPTRRN-UHFFFAOYSA-N 0.000 claims description 4
• WNTYNFHZYYRFOF-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-5-methyl-2-(pyridin-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC1=CC=CC=N1 WNTYNFHZYYRFOF-UHFFFAOYSA-N 0.000 claims description 4
• GGNIULHSXFVFEY-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-5-methyl-2-[(5-morpholin-4-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCOCC1 GGNIULHSXFVFEY-UHFFFAOYSA-N 0.000 claims description 4
• MZBKJNDTXYIZDF-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-5-methyl-2-[(5-pyrrolidin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCCC1 MZBKJNDTXYIZDF-UHFFFAOYSA-N 0.000 claims description 4
• WGOXOVKLYPJIKG-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[(5-pyrrolidin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(Br)=CC2=CN=C1NC(N=C1)=CC=C1N1CCCC1 WGOXOVKLYPJIKG-UHFFFAOYSA-N 0.000 claims description 4
• OWKQHMMRJQSCOI-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[[5-(2,6-dimethylmorpholin-4-yl)pyridin-2-yl]amino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)OC(C)CN1C(C=N1)=CC=C1NC1=NC=C(C(C)=C(Br)C(=O)N2C3CCCC3)C2=N1 OWKQHMMRJQSCOI-UHFFFAOYSA-N 0.000 claims description 4
• JQDVILMFUIXCRM-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[[5-(2-methoxyethoxy)pyridin-2-yl]amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CC(OCCOC)=CC=C1NC1=NC=C(C=C(Br)C(=O)N2C3CCCC3)C2=N1 JQDVILMFUIXCRM-UHFFFAOYSA-N 0.000 claims description 4
• ZJVMZDYQLYDXNY-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylsulfonylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3N=CC(=CC=3)S(=O)(=O)N3CCNCC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 ZJVMZDYQLYDXNY-UHFFFAOYSA-N 0.000 claims description 4
• HOXDMBXWILKORE-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 HOXDMBXWILKORE-UHFFFAOYSA-N 0.000 claims description 4
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• PGDFNFQEYKHGHT-UHFFFAOYSA-N 2-[[5-(3-aminopyrrolidine-1-carbonyl)pyridin-2-yl]amino]-8-cyclopentyl-6-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(CC)=CC2=CN=C1NC(N=C1)=CC=C1C(=O)N1CCC(N)C1 PGDFNFQEYKHGHT-UHFFFAOYSA-N 0.000 claims description 2
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• QHNTYPMGYAIFOW-UHFFFAOYSA-N 2-[[5-(azetidin-1-yl)pyridin-2-yl]amino]-6-benzyl-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C2=CN=C(NC=3N=CC(=CC=3)N3CCC3)N=C2N(C2CCCC2)C(=O)C=1CC1=CC=CC=C1 QHNTYPMGYAIFOW-UHFFFAOYSA-N 0.000 claims description 2
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• SQZKMAZDNSDTJA-UHFFFAOYSA-N 2-[[5-(azetidin-1-yl)pyridin-2-yl]amino]-8-cyclopentyl-6-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(CC)=CC2=CN=C1NC(N=C1)=CC=C1N1CCC1 SQZKMAZDNSDTJA-UHFFFAOYSA-N 0.000 claims description 2
• HYFURHDDUDBDNG-UHFFFAOYSA-N 2-[[5-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl]pyridin-2-yl]amino]-6-benzyl-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C(C)(N)C)CCN1C(C=N1)=CC=C1NC1=NC=C(C=C(CC=2C=CC=CC=2)C(=O)N2C3CCCC3)C2=N1 HYFURHDDUDBDNG-UHFFFAOYSA-N 0.000 claims description 2
• RUOXYZRWIGHCEO-UHFFFAOYSA-N 2-[[5-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl]pyridin-2-yl]amino]-8-cyclopentyl-6-(hydroxymethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C(C)(N)C)CCN1C(C=N1)=CC=C1NC1=NC=C(C=C(CO)C(=O)N2C3CCCC3)C2=N1 RUOXYZRWIGHCEO-UHFFFAOYSA-N 0.000 claims description 2
• AJTLUUIVYUJUMP-UHFFFAOYSA-N 2-[[5-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl]pyridin-2-yl]amino]-8-cyclopentyl-6-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(CC)=CC2=CN=C1NC(N=C1)=CC=C1N1CCC(C(C)(C)N)C1 AJTLUUIVYUJUMP-UHFFFAOYSA-N 0.000 claims description 2
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• 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
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