OA12755A - 2-(pyridin-2-ylamino)-pyridoÄ2,3dÜpyrimidin-7-ones. - Google Patents

Info

Publication number

OA12755A

OA12755A OA1200400189A OA1200400189A OA12755A OA 12755 A OA12755 A OA 12755A OA 1200400189 A OA1200400189 A OA 1200400189A OA 1200400189 A OA1200400189 A OA 1200400189A OA 12755 A OA12755 A OA 12755A

Authority

OA

OAPI

Prior art keywords

pyrido

pyridin

pyrimidin

ylamino

cyclopentyl

Prior art date

2002-01-22

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• 150000001875 compounds Chemical class 0.000 claims abstract description 108
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 82
• -1 trifluoromethylalkyl Chemical group 0.000 claims description 78
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
• 125000000217 alkyl group Chemical group 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
• 239000002253 acid Substances 0.000 claims description 31
• 239000001257 hydrogen Substances 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 27
• 229920002554 vinyl polymer Polymers 0.000 claims description 27
• 150000002148 esters Chemical class 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 208000035475 disorder Diseases 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 206010028980 Neoplasm Diseases 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 125000002837 carbocyclic group Chemical group 0.000 claims description 13
• 201000010099 disease Diseases 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• 229910020008 S(O) Inorganic materials 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
• 150000002825 nitriles Chemical class 0.000 claims description 12
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
• WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 claims description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 239000011593 sulfur Substances 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
• 239000000651 prodrug Substances 0.000 claims description 10
• 229940002612 prodrug Drugs 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 208000009956 adenocarcinoma Diseases 0.000 claims description 9
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
• 150000001408 amides Chemical class 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
• 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 7
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 6
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 210000003800 pharynx Anatomy 0.000 claims description 6
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 230000002159 abnormal effect Effects 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• 150000001450 anions Chemical class 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 210000000481 breast Anatomy 0.000 claims description 4
• 241001493065 dsRNA viruses Species 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 210000002307 prostate Anatomy 0.000 claims description 4
• 210000003491 skin Anatomy 0.000 claims description 4
• 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 3
• LQPZBOPWZYJOPA-UHFFFAOYSA-N 4-[6-[[8-cyclopentyl-6-(methoxymethyl)-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylic acid Chemical compound N1=C2N(C3CCCC3)C(=O)C(COC)=CC2=CN=C1NC(N=C1)=CC=C1N1CCN(C(O)=O)CC1 LQPZBOPWZYJOPA-UHFFFAOYSA-N 0.000 claims description 3
• USXVSXDTKIDDDT-UHFFFAOYSA-N 8-cyclopentyl-6-(2-methoxyethoxymethyl)-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(COCCOC)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 USXVSXDTKIDDDT-UHFFFAOYSA-N 0.000 claims description 3
• TUHDWYREOHGIHM-UHFFFAOYSA-N 8-cyclopropyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC3)C(=O)C=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 TUHDWYREOHGIHM-UHFFFAOYSA-N 0.000 claims description 3
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• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 201000009030 Carcinoma Diseases 0.000 claims description 3
• 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims description 3
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
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• 206010017533 Fungal infection Diseases 0.000 claims description 3
• 206010073069 Hepatic cancer Diseases 0.000 claims description 3
• 208000017604 Hodgkin disease Diseases 0.000 claims description 3
• XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 3
• 206010023347 Keratoacanthoma Diseases 0.000 claims description 3
• 208000031888 Mycoses Diseases 0.000 claims description 3
• 206010029260 Neuroblastoma Diseases 0.000 claims description 3
• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 201000010208 Seminoma Diseases 0.000 claims description 3
• 206010052779 Transplant rejections Diseases 0.000 claims description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
• 206010057469 Vascular stenosis Diseases 0.000 claims description 3
• 201000001531 bladder carcinoma Diseases 0.000 claims description 3
• 210000000988 bone and bone Anatomy 0.000 claims description 3
• 210000003169 central nervous system Anatomy 0.000 claims description 3
• 210000003679 cervix uteri Anatomy 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
• CKAATXLOPOIZQJ-UHFFFAOYSA-N ethyl 8-cyclopentyl-7-oxo-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidine-6-carboxylate;hydrochloride Chemical compound Cl.N1=C2N(C3CCCC3)C(=O)C(C(=O)OCC)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 CKAATXLOPOIZQJ-UHFFFAOYSA-N 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
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• 208000003849 large cell carcinoma Diseases 0.000 claims description 3
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• 210000004072 lung Anatomy 0.000 claims description 3
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• 210000000214 mouth Anatomy 0.000 claims description 3
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• 210000002464 muscle smooth vascular Anatomy 0.000 claims description 3
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• 210000000664 rectum Anatomy 0.000 claims description 3
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• 210000002784 stomach Anatomy 0.000 claims description 3
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• 210000001685 thyroid gland Anatomy 0.000 claims description 3
• 210000002105 tongue Anatomy 0.000 claims description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 3
• 208000010576 undifferentiated carcinoma Diseases 0.000 claims description 3
• 241001529453 unidentified herpesvirus Species 0.000 claims description 3
• 208000010570 urinary bladder carcinoma Diseases 0.000 claims description 3
• QHXAANLQXKLJSI-UHFFFAOYSA-N 2-[(5-piperazin-1-ylpyridin-2-yl)amino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C)C2=NC=1NC(N=C1)=CC=C1N1CCNCC1 QHXAANLQXKLJSI-UHFFFAOYSA-N 0.000 claims description 2
• DGXNULHJVNJWJP-UHFFFAOYSA-N 2-[[5-(3-aminopyrrolidin-1-yl)pyridin-2-yl]amino]-6-bromo-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(N)CCN1C(C=N1)=CC=C1NC1=NC=C(C=C(Br)C(=O)N2C3CCCC3)C2=N1 DGXNULHJVNJWJP-UHFFFAOYSA-N 0.000 claims description 2
• GDHUHDALUPEYNQ-UHFFFAOYSA-N 2-[[5-[bis(2-hydroxyethyl)amino]pyridin-2-yl]amino]-6-bromo-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CC(N(CCO)CCO)=CC=C1NC1=NC=C(C=C(Br)C(=O)N2C3CCCC3)C2=N1 GDHUHDALUPEYNQ-UHFFFAOYSA-N 0.000 claims description 2
• FUPSONGCEPFMNO-UHFFFAOYSA-N 2-[[5-[bis(2-methoxyethyl)amino]pyridin-2-yl]amino]-6-bromo-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CC(N(CCOC)CCOC)=CC=C1NC1=NC=C(C=C(Br)C(=O)N2C3CCCC3)C2=N1 FUPSONGCEPFMNO-UHFFFAOYSA-N 0.000 claims description 2
• CSLVCGOGMKYULP-UHFFFAOYSA-N 4-[6-[(6-bromo-8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]pyridin-3-yl]-2,2-dimethylpiperazine-1-carboxylic acid Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CC(C)(C)N(C(O)=O)CC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 CSLVCGOGMKYULP-UHFFFAOYSA-N 0.000 claims description 2
• GOKQANFHKKJYJK-UHFFFAOYSA-N 4-[6-[[8-cyclopentyl-6-(2-methoxyethoxymethyl)-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylic acid Chemical compound N1=C2N(C3CCCC3)C(=O)C(COCCOC)=CC2=CN=C1NC(N=C1)=CC=C1N1CCN(C(O)=O)CC1 GOKQANFHKKJYJK-UHFFFAOYSA-N 0.000 claims description 2
• XVWOBTDIUVVUQN-UHFFFAOYSA-N 6-acetyl-2-[[5-(3,4-dihydroxypyrrolidin-1-yl)pyridin-2-yl]amino]-8-(methoxymethyl)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=C(C(C)=O)C(=O)N(COC)C2=NC=1NC(N=C1)=CC=C1N1CC(O)C(O)C1 XVWOBTDIUVVUQN-UHFFFAOYSA-N 0.000 claims description 2
• TVIIOMIQYPDRNN-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-2-[[5-(dimethylamino)pyridin-2-yl]amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CC(N(C)C)=CC=C1NC1=NC=C(C=C(C(C)=O)C(=O)N2C3CCCC3)C2=N1 TVIIOMIQYPDRNN-UHFFFAOYSA-N 0.000 claims description 2
• CTQWHSWXTOSBOZ-UHFFFAOYSA-N 6-amino-2-[[5-(azepan-1-yl)pyridin-2-yl]amino]-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(N)=CC2=CN=C1NC(N=C1)=CC=C1N1CCCCCC1 CTQWHSWXTOSBOZ-UHFFFAOYSA-N 0.000 claims description 2
• WXQRJGNEEAQTOZ-UHFFFAOYSA-N 6-amino-2-[[5-(azetidin-1-yl)pyridin-2-yl]amino]-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(N)=CC2=CN=C1NC(N=C1)=CC=C1N1CCC1 WXQRJGNEEAQTOZ-UHFFFAOYSA-N 0.000 claims description 2
• UOMYGSOEHPHNDW-UHFFFAOYSA-N 6-amino-2-[[5-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl]pyridin-2-yl]amino]-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C(C)(N)C)CCN1C(C=N1)=CC=C1NC1=NC=C(C=C(N)C(=O)N2C3CCCC3)C2=N1 UOMYGSOEHPHNDW-UHFFFAOYSA-N 0.000 claims description 2
• MLWBUGTZSYZSKA-UHFFFAOYSA-N 6-benzyl-8-cyclopentyl-2-[(5-pyrrolidin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C2=CN=C(NC=3N=CC(=CC=3)N3CCCC3)N=C2N(C2CCCC2)C(=O)C=1CC1=CC=CC=C1 MLWBUGTZSYZSKA-UHFFFAOYSA-N 0.000 claims description 2
• PGAVCQQDFMARHD-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[(5-phenylpyridin-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=C1C1=CC=CC=C1 PGAVCQQDFMARHD-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• ZTDQCLRXMQBMCJ-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[[5-(3,5-dimethylpiperazine-1-carbonyl)pyridin-2-yl]amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)NC(C)CN1C(=O)C(C=N1)=CC=C1NC1=NC=C(C=C(Br)C(=O)N2C3CCCC3)C2=N1 ZTDQCLRXMQBMCJ-UHFFFAOYSA-N 0.000 claims description 2
• FUCCMUBSBLDUQL-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-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(Br)C(=O)N2C3CCCC3)C2=N1 FUCCMUBSBLDUQL-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• IEQUHIKSZOVGIM-UHFFFAOYSA-N 8-cyclopentyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 IEQUHIKSZOVGIM-UHFFFAOYSA-N 0.000 claims description 2
• MJZOPCRPMSQOEJ-UHFFFAOYSA-N 8-cyclopentyl-2-[[5-(3,5-dimethylpiperazine-1-carbonyl)pyridin-2-yl]amino]-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)N1CC(C)NC(C)C1 MJZOPCRPMSQOEJ-UHFFFAOYSA-N 0.000 claims description 2
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• RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 2
• 229960001171 acetohydroxamic acid Drugs 0.000 claims description 2
• 210000000133 brain stem Anatomy 0.000 claims description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 210000002429 large intestine Anatomy 0.000 claims description 2
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• 150000002431 hydrogen Chemical class 0.000 claims 6
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• 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 2
• HCHPAUZGDOEZFK-UHFFFAOYSA-N 1-[6-[(6-benzyl-8-cyclopentyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]pyridin-3-yl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCCN1C(C=N1)=CC=C1NC1=NC=C(C=C(CC=2C=CC=CC=2)C(=O)N2C3CCCC3)C2=N1 HCHPAUZGDOEZFK-UHFFFAOYSA-N 0.000 claims 1
• ULKGZICJKDSXKY-UHFFFAOYSA-N 2-[(5-anilinopyridin-2-yl)amino]-6-bromo-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(Br)=CC2=CN=C1NC(N=C1)=CC=C1NC1=CC=CC=C1 ULKGZICJKDSXKY-UHFFFAOYSA-N 0.000 claims 1
• FEXBSYZCPACDNP-UHFFFAOYSA-N 2-[[5-(3-aminopyrrolidine-1-carbonyl)pyridin-2-yl]amino]-6-bromo-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(N)CCN1C(=O)C(C=N1)=CC=C1NC1=NC=C(C=C(Br)C(=O)N2C3CCCC3)C2=N1 FEXBSYZCPACDNP-UHFFFAOYSA-N 0.000 claims 1
• KRWHAQTXQAMXTB-UHFFFAOYSA-N 2-[[5-(azepan-1-yl)pyridin-2-yl]amino]-6-bromo-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(Br)=CC2=CN=C1NC(N=C1)=CC=C1N1CCCCCC1 KRWHAQTXQAMXTB-UHFFFAOYSA-N 0.000 claims 1
• 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 1
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