JP5643110B2 - ピロロピリミジン類およびピロロピリジン類 - Google Patents

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Publication number

JP5643110B2

JP5643110B2 JP2010541794A JP2010541794A JP5643110B2 JP 5643110 B2 JP5643110 B2 JP 5643110B2 JP 2010541794 A JP2010541794 A JP 2010541794A JP 2010541794 A JP2010541794 A JP 2010541794A JP 5643110 B2 JP5643110 B2 JP 5643110B2

Authority

JP

Japan

Prior art keywords

pyridin

methyl

phenyl

pyrrolo

alkyl

Prior art date

2008-01-11

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 - Fee Related

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• 150000005255 pyrrolopyridines Chemical class 0.000 title 1
• 150000004944 pyrrolopyrimidines Chemical class 0.000 title 1
• -1 hydroxy, carboxy Chemical group 0.000 claims description 429
• 150000001875 compounds Chemical class 0.000 claims description 174
• 150000003839 salts Chemical group 0.000 claims description 65
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 40
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
• 229910052799 carbon Inorganic materials 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000004043 oxo group Chemical group O=* 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 14
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• MXCNQDNBZSXROM-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridine-3-carboxamide Chemical compound CN(C)CCCNC(=O)C1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 MXCNQDNBZSXROM-UHFFFAOYSA-N 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 150000001408 amides Chemical class 0.000 claims description 8
• SCHKFZAJUXSFRW-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-pyridin-3-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=NC=CC=3)N=2)=N1 SCHKFZAJUXSFRW-UHFFFAOYSA-N 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• MTDLDOSLLNBXFQ-UHFFFAOYSA-N 4-(5-bromopyridin-3-yl)-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(Br)C=NC=3)N=2)=N1 MTDLDOSLLNBXFQ-UHFFFAOYSA-N 0.000 claims description 5
• GEZBFRYAHDIKJC-UHFFFAOYSA-N 4-[5-[3-(4-methylpiperazin-1-yl)prop-1-ynyl]pyridin-3-yl]-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CN(C)CCN1CC#CC1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 GEZBFRYAHDIKJC-UHFFFAOYSA-N 0.000 claims description 5
• 125000003368 amide group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000003118 aryl group Chemical group 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 claims description 3
• QCRHVPBKVXLXAP-UHFFFAOYSA-N methyl 2-[[3-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methylamino]acetate Chemical compound COC(=O)CNCC1=CC=CC(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 QCRHVPBKVXLXAP-UHFFFAOYSA-N 0.000 claims description 3
• SYJFZTDWCDUBEA-UHFFFAOYSA-N n-ethyl-5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridine-3-carboxamide Chemical compound CCNC(=O)C1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 SYJFZTDWCDUBEA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 3
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 3
• LXFOUHUCGLAACZ-RUZDIDTESA-N (3r)-n,n-dimethyl-1-[[4-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methyl]pyrrolidin-3-amine Chemical compound C1[C@H](N(C)C)CCN1CC1=CC=C(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)C=C1 LXFOUHUCGLAACZ-RUZDIDTESA-N 0.000 claims description 2
• LXFOUHUCGLAACZ-VWLOTQADSA-N (3s)-n,n-dimethyl-1-[[4-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methyl]pyrrolidin-3-amine Chemical compound C1[C@@H](N(C)C)CCN1CC1=CC=C(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)C=C1 LXFOUHUCGLAACZ-VWLOTQADSA-N 0.000 claims description 2
• IUHKCKCHJIPNLZ-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[3-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 IUHKCKCHJIPNLZ-UHFFFAOYSA-N 0.000 claims description 2
• XRZAJUASIZMKJA-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[5-(2-pyridin-2-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyridin-3-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=CC=CC=2)C=C1 XRZAJUASIZMKJA-UHFFFAOYSA-N 0.000 claims description 2
• HUDVSUWRPXEPQG-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)C=C1 HUDVSUWRPXEPQG-UHFFFAOYSA-N 0.000 claims description 2
• BYYVXSJCSCCLEE-UHFFFAOYSA-N 1-[4-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]ethanamine Chemical compound C1=CC(C(N)C)=CC=C1C1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 BYYVXSJCSCCLEE-UHFFFAOYSA-N 0.000 claims description 2
• PYHAVULIUAHIMD-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-(5-phenylpyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC=CC=3)N=2)=N1 PYHAVULIUAHIMD-UHFFFAOYSA-N 0.000 claims description 2
• MPYFLSGEPMMEGV-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-[5-(3-piperazin-2-ylphenyl)pyridin-3-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=C(C=CC=3)C3NCCNC3)N=2)=N1 MPYFLSGEPMMEGV-UHFFFAOYSA-N 0.000 claims description 2
• QRGPLIHBZDOWQY-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-[5-(3-pyrrolidin-1-ylphenyl)pyridin-3-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=C(C=CC=3)N3CCCC3)N=2)=N1 QRGPLIHBZDOWQY-UHFFFAOYSA-N 0.000 claims description 2
• HRLDJGYLFZPGCT-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-[5-(3-pyrrolidin-2-ylphenyl)pyridin-3-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=C(C=CC=3)C3NCCC3)N=2)=N1 HRLDJGYLFZPGCT-UHFFFAOYSA-N 0.000 claims description 2
• NEJLMEBMYFJVAB-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-[5-(4-piperazin-2-ylphenyl)pyridin-3-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(=CC=3)C3NCCNC3)N=2)=N1 NEJLMEBMYFJVAB-UHFFFAOYSA-N 0.000 claims description 2
• AYADTPBBVYKLCC-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-[5-(4-piperidin-1-ylphenyl)pyridin-3-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(=CC=3)N3CCCCC3)N=2)=N1 AYADTPBBVYKLCC-UHFFFAOYSA-N 0.000 claims description 2
• RFJRMCAMYRCLTG-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-[5-[3-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]pyridin-3-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CN(C(C)C)CCN1CC1=CC=CC(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 RFJRMCAMYRCLTG-UHFFFAOYSA-N 0.000 claims description 2
• URGBVACVJQIZQQ-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-[5-[4-(4-propan-2-ylpiperazin-1-yl)phenyl]pyridin-3-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CN(C(C)C)CCN1C1=CC=C(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)C=C1 URGBVACVJQIZQQ-UHFFFAOYSA-N 0.000 claims description 2
• NDTDKLFOJIHKRT-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-4-[5-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]pyridin-3-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CN(C(C)C)CCN1CC1=CC=C(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)C=C1 NDTDKLFOJIHKRT-UHFFFAOYSA-N 0.000 claims description 2
• GXPIGLBXXCBLJE-UHFFFAOYSA-N 2-[3-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]propan-2-amine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=C(C=CC=3)C(C)(C)N)N=2)=N1 GXPIGLBXXCBLJE-UHFFFAOYSA-N 0.000 claims description 2
• MOBBOEPUEXEXSB-UHFFFAOYSA-N 2-[4-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]propan-2-amine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(=CC=3)C(C)(C)N)N=2)=N1 MOBBOEPUEXEXSB-UHFFFAOYSA-N 0.000 claims description 2
• KREWTGVYWDJLSU-UHFFFAOYSA-N 2-[[3-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methylamino]acetic acid Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=C(CNCC(O)=O)C=CC=3)N=2)=N1 KREWTGVYWDJLSU-UHFFFAOYSA-N 0.000 claims description 2
• JROXKCZQHDIMLB-UHFFFAOYSA-N 2-[[3-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methylamino]ethanol Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=C(CNCCO)C=CC=3)N=2)=N1 JROXKCZQHDIMLB-UHFFFAOYSA-N 0.000 claims description 2
• PIMASRUZLJHZPG-UHFFFAOYSA-N 2-[[4-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methylamino]acetic acid Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CNCC(O)=O)=CC=3)N=2)=N1 PIMASRUZLJHZPG-UHFFFAOYSA-N 0.000 claims description 2
• LTKBZHFFIZWAGM-UHFFFAOYSA-N 2-[[4-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methylamino]ethanol Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CNCCO)=CC=3)N=2)=N1 LTKBZHFFIZWAGM-UHFFFAOYSA-N 0.000 claims description 2
• HYDOTRODUPBFON-UHFFFAOYSA-N 2-[methyl-[[3-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methyl]amino]ethanol Chemical compound OCCN(C)CC1=CC=CC(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 HYDOTRODUPBFON-UHFFFAOYSA-N 0.000 claims description 2
• BAUSZGZXLWQTSV-UHFFFAOYSA-N 3-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]quinoline Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C4C=CC=CC4=NC=3)N=2)=N1 BAUSZGZXLWQTSV-UHFFFAOYSA-N 0.000 claims description 2
• YILCKKXTQRISFS-UHFFFAOYSA-N 3-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenol Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=C(O)C=CC=3)N=2)=N1 YILCKKXTQRISFS-UHFFFAOYSA-N 0.000 claims description 2
• IGHNQSOWQXRDPP-UHFFFAOYSA-N 3-amino-n-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]propanamide Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(NC(=O)CCN)C=NC=3)N=2)=N1 IGHNQSOWQXRDPP-UHFFFAOYSA-N 0.000 claims description 2
• DEMONGQTHRCUTI-UHFFFAOYSA-N 3-hydroxy-n-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]propanamide Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(NC(=O)CCO)C=NC=3)N=2)=N1 DEMONGQTHRCUTI-UHFFFAOYSA-N 0.000 claims description 2
• KZYCBVMCFDXQCH-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C(=CC=NC=3)C)N=2)=N1 KZYCBVMCFDXQCH-UHFFFAOYSA-N 0.000 claims description 2
• IVMDEMYMESGWMX-UHFFFAOYSA-N 4-(5-bromopyridin-3-yl)-2-pyridin-2-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound BrC1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=CC=CC=2)=C1 IVMDEMYMESGWMX-UHFFFAOYSA-N 0.000 claims description 2
• LGRXCUGDUKYTII-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 LGRXCUGDUKYTII-UHFFFAOYSA-N 0.000 claims description 2
• FICRHWLCCPXOAU-UHFFFAOYSA-N 4-(5-methylpyridin-3-yl)-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 FICRHWLCCPXOAU-UHFFFAOYSA-N 0.000 claims description 2
• XHTJVHNAENKMKQ-UHFFFAOYSA-N 4-(dimethylamino)-n-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]butanamide Chemical compound CN(C)CCCC(=O)NC1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 XHTJVHNAENKMKQ-UHFFFAOYSA-N 0.000 claims description 2
• IFQFBXRUWMZDFF-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]isoquinoline Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C4=CC=CC=C4C=NC=3)N=2)=N1 IFQFBXRUWMZDFF-UHFFFAOYSA-N 0.000 claims description 2
• GKICBBLOQKIKCQ-UHFFFAOYSA-N 4-[5-(1-methylpyrazol-4-yl)pyridin-3-yl]-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C3=CN(C)N=C3)N=2)=N1 GKICBBLOQKIKCQ-UHFFFAOYSA-N 0.000 claims description 2
• VLEUJJOIFNNCLV-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)pyridin-3-yl]-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C(=CC=CC=3)F)N=2)=N1 VLEUJJOIFNNCLV-UHFFFAOYSA-N 0.000 claims description 2
• RQTZAECQLIPPMK-UHFFFAOYSA-N 4-[5-(2-methoxyphenyl)pyridin-3-yl]-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=CC=C1C1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 RQTZAECQLIPPMK-UHFFFAOYSA-N 0.000 claims description 2
• OAOCGQNMPOSYNM-UHFFFAOYSA-N 4-[5-(2-methylphenyl)pyridin-3-yl]-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C(=CC=CC=3)C)N=2)=N1 OAOCGQNMPOSYNM-UHFFFAOYSA-N 0.000 claims description 2
• MFHMMVSFBXFYOD-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)pyridin-3-yl]-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=CC(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 MFHMMVSFBXFYOD-UHFFFAOYSA-N 0.000 claims description 2
• YSKLBQRYOILDLL-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)pyridin-3-yl]-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(F)=CC=3)N=2)=N1 YSKLBQRYOILDLL-UHFFFAOYSA-N 0.000 claims description 2
• BDEVKFCRUCIJNB-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)pyridin-3-yl]-2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 BDEVKFCRUCIJNB-UHFFFAOYSA-N 0.000 claims description 2
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• FLPPSAHXWAZNJC-UHFFFAOYSA-N methyl 2-[[4-(5-bromopyridin-3-yl)phenyl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate Chemical compound C1=CC(CN(CC(=O)OC)C(=O)OC(C)(C)C)=CC=C1C1=CN=CC(Br)=C1 FLPPSAHXWAZNJC-UHFFFAOYSA-N 0.000 description 2
• LDMCBYMOECQAOV-UHFFFAOYSA-N methyl 2-[[4-(5-bromopyridin-3-yl)phenyl]methyl-methylamino]acetate Chemical compound C1=CC(CN(C)CC(=O)OC)=CC=C1C1=CN=CC(Br)=C1 LDMCBYMOECQAOV-UHFFFAOYSA-N 0.000 description 2
• KGADXMWLVNOSLW-UHFFFAOYSA-N methyl 2-[[4-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methylamino]acetate Chemical compound C1=CC(CNCC(=O)OC)=CC=C1C1=CN=CC(C=2C=3C=CNC=3N=C(N=2)C=2N=C(C)C=CC=2)=C1 KGADXMWLVNOSLW-UHFFFAOYSA-N 0.000 description 2
• DODOVYXGBUMKCM-UHFFFAOYSA-N methyl 3-[4-(5-bromopyridin-3-yl)phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CN=CC(Br)=C1 DODOVYXGBUMKCM-UHFFFAOYSA-N 0.000 description 2
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