JP2011509279A5 - - Google Patents
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- JP2011509279A5 JP2011509279A5 JP2010541794A JP2010541794A JP2011509279A5 JP 2011509279 A5 JP2011509279 A5 JP 2011509279A5 JP 2010541794 A JP2010541794 A JP 2010541794A JP 2010541794 A JP2010541794 A JP 2010541794A JP 2011509279 A5 JP2011509279 A5 JP 2011509279A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- methyl
- pyrrolo
- phenyl
- alkyl
- Prior art date
- 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.)
- Granted
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- -1 hydroxy, carboxy Chemical group 0.000 claims 229
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 30
- 125000001475 halogen functional group Chemical group 0.000 claims 18
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- 239000012453 solvate Substances 0.000 claims 14
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 13
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 210000000988 bone and bone Anatomy 0.000 claims 5
- 125000004193 piperazinyl group Chemical group 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical group 0.000 claims 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- 206010006956 Calcium deficiency Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- XONWJRHRGYJPBA-UHFFFAOYSA-N [4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]methanamine Chemical class CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CN)=CC=3)C=2)=N1 XONWJRHRGYJPBA-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 125000006038 hexenyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 230000011164 ossification Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 2
- 230000000638 stimulation Effects 0.000 claims 2
- 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 2
- KILIYQSGUAKAHL-QGZVFWFLSA-N (1r)-1-[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]ethanamine Chemical compound C1=CC([C@H](N)C)=CC=C1C1=CN=CC(C=2C=3C=CNC=3N=C(C=2)C=2N=C(C)C=CC=2)=C1 KILIYQSGUAKAHL-QGZVFWFLSA-N 0.000 claims 1
- KILIYQSGUAKAHL-KRWDZBQOSA-N (1s)-1-[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]ethanamine Chemical compound C1=CC([C@@H](N)C)=CC=C1C1=CN=CC(C=2C=3C=CNC=3N=C(C=2)C=2N=C(C)C=CC=2)=C1 KILIYQSGUAKAHL-KRWDZBQOSA-N 0.000 claims 1
- GXVMKMKFKPPUNO-SANMLTNESA-N (3s)-n,n-dimethyl-1-[[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-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(C=2)C=2N=C(C)C=CC=2)C=C1 GXVMKMKFKPPUNO-SANMLTNESA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- CMCLWFVUQYCJJS-UHFFFAOYSA-N 1-[[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]methyl]azetidin-3-ol Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CN4CC(O)C4)=CC=3)C=2)=N1 CMCLWFVUQYCJJS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- FFPRTDNOWIKLBA-UHFFFAOYSA-N 2-[2-methyl-4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-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)C(=CC=3)C(C)(C)N)C=2)=N1 FFPRTDNOWIKLBA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KKEFAVBQMOOGBH-UHFFFAOYSA-N 2-[3-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]acetic acid Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=C(CC(O)=O)C=CC=3)C=2)=N1 KKEFAVBQMOOGBH-UHFFFAOYSA-N 0.000 claims 1
- FIPZROHBLDNPTC-UHFFFAOYSA-N 2-[3-methyl-4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-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)C)C=2)=N1 FIPZROHBLDNPTC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- OFCTUOWIXHEUBZ-UHFFFAOYSA-N 2-[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]acetic acid Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CC(O)=O)=CC=3)C=2)=N1 OFCTUOWIXHEUBZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- BXZSGRJWIZKRIB-UHFFFAOYSA-N 2-[[3-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-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)C=2)=N1 BXZSGRJWIZKRIB-UHFFFAOYSA-N 0.000 claims 1
- XMJGNVJNEQFAAH-UHFFFAOYSA-N 2-[[3-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-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)C=2)=N1 XMJGNVJNEQFAAH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- ZVMPMYPIRLXSEW-UHFFFAOYSA-N 2-[[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-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)C=2)=N1 ZVMPMYPIRLXSEW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- DVOCDGDCDMUDER-UHFFFAOYSA-N 2-[methyl-[[3-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]methyl]amino]acetic acid Chemical compound OC(=O)CN(C)CC1=CC=CC(C=2C=C(C=NC=2)C=2C=3C=CNC=3N=C(C=2)C=2N=C(C)C=CC=2)=C1 DVOCDGDCDMUDER-UHFFFAOYSA-N 0.000 claims 1
- IIXKGKWUCCUOTF-UHFFFAOYSA-N 2-[methyl-[[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]methyl]amino]acetic acid Chemical compound C1=CC(CN(CC(O)=O)C)=CC=C1C1=CN=CC(C=2C=3C=CNC=3N=C(C=2)C=2N=C(C)C=CC=2)=C1 IIXKGKWUCCUOTF-UHFFFAOYSA-N 0.000 claims 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- DUIPAMHVKRFBED-UHFFFAOYSA-N 2-pyridin-2-yl-4-pyridin-3-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=C2NC=CC2=C(C=2C=NC=CC=2)N=C1C1=CC=CC=N1 DUIPAMHVKRFBED-UHFFFAOYSA-N 0.000 claims 1
- DPASXGNZPSLEBK-UHFFFAOYSA-N 2-pyrrolidin-1-ylpyridin-3-amine Chemical compound NC1=CC=CN=C1N1CCCC1 DPASXGNZPSLEBK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HYCCLCZIAPOJGJ-UHFFFAOYSA-N 3-[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]propanoic acid Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CCC(O)=O)=CC=3)C=2)=N1 HYCCLCZIAPOJGJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- REFHIBRQXDTUTD-UHFFFAOYSA-N 3-[[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]methylamino]propan-1-ol Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CNCCCO)=CC=3)C=2)=N1 REFHIBRQXDTUTD-UHFFFAOYSA-N 0.000 claims 1
- REHLMBWOMDJPSA-UHFFFAOYSA-N 3-[[4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]methylamino]propanoic acid Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CNCCC(O)=O)=CC=3)C=2)=N1 REHLMBWOMDJPSA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
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- STYXKLQEDTXSMF-UHFFFAOYSA-N [4-[5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]phenyl]methanol Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CO)=CC=3)N=2)=N1 STYXKLQEDTXSMF-UHFFFAOYSA-N 0.000 claims 1
- YWAJAWHYUCEJME-UHFFFAOYSA-N [4-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]phenyl]methanol Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(C=NC=3)C=3C=CC(CO)=CC=3)C=2)=N1 YWAJAWHYUCEJME-UHFFFAOYSA-N 0.000 claims 1
- QOCNILQZUNXLLW-UHFFFAOYSA-N [5-[2-(6-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyridin-3-yl]methanol Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(CO)C=NC=3)N=2)=N1 QOCNILQZUNXLLW-UHFFFAOYSA-N 0.000 claims 1
- JRUPUVSUHYFWEW-UHFFFAOYSA-N [5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyridin-3-yl]methanol Chemical compound CC1=CC=CC(C=2N=C3NC=CC3=C(C=3C=C(CO)C=NC=3)C=2)=N1 JRUPUVSUHYFWEW-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
- GKWLRXGCXNXMLP-UHFFFAOYSA-N methyl 2-[[3-[5-[6-(6-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-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(C=2)C=2N=C(C)C=CC=2)=C1 GKWLRXGCXNXMLP-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
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-
2009
- 2009-01-08 AR ARP090100050A patent/AR070127A1/es not_active Application Discontinuation
- 2009-01-09 TW TW098100815A patent/TW200934781A/zh unknown
- 2009-01-09 WO PCT/EP2009/050225 patent/WO2009087225A2/en not_active Ceased
- 2009-01-09 KR KR1020107017744A patent/KR20100116606A/ko not_active Withdrawn
- 2009-01-09 BR BRPI0907231A patent/BRPI0907231A2/pt not_active IP Right Cessation
- 2009-01-09 AU AU2009203694A patent/AU2009203694B2/en not_active Ceased
- 2009-01-09 MX MX2010007605A patent/MX2010007605A/es active IP Right Grant
- 2009-01-09 EP EP20090700871 patent/EP2242756A2/en not_active Withdrawn
- 2009-01-09 CN CN200980108446.3A patent/CN101970435B/zh not_active Expired - Fee Related
- 2009-01-09 US US12/351,438 patent/US8314112B2/en not_active Expired - Fee Related
- 2009-01-09 CA CA2711845A patent/CA2711845A1/en not_active Abandoned
- 2009-01-09 EA EA201001126A patent/EA201001126A1/ru unknown
- 2009-01-09 PE PE2009000024A patent/PE20091306A1/es not_active Application Discontinuation
- 2009-01-09 JP JP2010541794A patent/JP5643110B2/ja not_active Expired - Fee Related
- 2009-01-09 CL CL2009000028A patent/CL2009000028A1/es unknown
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2010
- 2010-06-30 MA MA32971A patent/MA31952B1/fr unknown
- 2010-06-30 ZA ZA2010/04602A patent/ZA201004602B/en unknown
- 2010-06-30 TN TN2010000305A patent/TN2010000305A1/fr unknown
- 2010-07-02 CR CR11554A patent/CR11554A/es not_active Application Discontinuation
- 2010-07-05 IL IL206819A patent/IL206819A0/en unknown
- 2010-07-09 EC EC2010010335A patent/ECSP10010335A/es unknown
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