JP2009523812A5 - - Google Patents
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- JP2009523812A5 JP2009523812A5 JP2008551416A JP2008551416A JP2009523812A5 JP 2009523812 A5 JP2009523812 A5 JP 2009523812A5 JP 2008551416 A JP2008551416 A JP 2008551416A JP 2008551416 A JP2008551416 A JP 2008551416A JP 2009523812 A5 JP2009523812 A5 JP 2009523812A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- pyridin
- alkyl
- benzyl
- phenyl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 91
- 125000000304 alkynyl group Chemical group 0.000 claims 50
- 125000003342 alkenyl group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000004414 alkyl thio group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- -1 R 22a Chemical compound 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims 2
- 206010014733 Endometrial cancer Diseases 0.000 claims 2
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 239000012830 cancer therapeutic Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- LSAAIXBCZXQBIF-AWEZNQCLSA-N (2s)-3,3-dimethyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]butan-2-amine Chemical compound C1=CC(CN[C@@H](C)C(C)(C)C)=CC=C1C1=CC=NC2=C1C=CN2 LSAAIXBCZXQBIF-AWEZNQCLSA-N 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- MXHDTPHQKKJTFP-ONEGZZNKSA-N (e)-4-[4-(3-acetyl-1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]but-3-en-2-one Chemical compound C1=CC(/C=C/C(=O)C)=CC=C1C1=CC=NC2=C1C(C(C)=O)=CN2 MXHDTPHQKKJTFP-ONEGZZNKSA-N 0.000 claims 1
- RIBOCHYWSQMSPG-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound FC1=CC=CC=C1NC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 RIBOCHYWSQMSPG-UHFFFAOYSA-N 0.000 claims 1
- JBOWFZLIHYJIJV-UHFFFAOYSA-N 1-(2-fluorophenyl)-n-[[5-(1h-pyrrolo[2,3-b]pyridin-4-yl)thiophen-2-yl]methyl]methanamine Chemical compound FC1=CC=CC=C1CNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)S1 JBOWFZLIHYJIJV-UHFFFAOYSA-N 0.000 claims 1
- XCZIUZRMJVRXAO-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound FC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 XCZIUZRMJVRXAO-UHFFFAOYSA-N 0.000 claims 1
- SHYZHDIDMSOIML-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 SHYZHDIDMSOIML-UHFFFAOYSA-N 0.000 claims 1
- WHYZTAZVBTUCOH-UHFFFAOYSA-N 1-(4-methylphenyl)-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]methanamine Chemical compound C1=CC(C)=CC=C1CNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 WHYZTAZVBTUCOH-UHFFFAOYSA-N 0.000 claims 1
- HVTOEFSLOQHZTL-UHFFFAOYSA-N 1-(4-naphthalen-2-yl-1h-pyrrolo[2,3-b]pyridin-3-yl)ethanone Chemical compound C1=CC=CC2=CC(C=3C=CN=C4NC=C(C=34)C(=O)C)=CC=C21 HVTOEFSLOQHZTL-UHFFFAOYSA-N 0.000 claims 1
- FKGARMNFEGUUFP-UHFFFAOYSA-N 1-(4-phenyl-1h-pyrrolo[2,3-b]pyridin-3-yl)ethanone Chemical compound C=12C(C(=O)C)=CNC2=NC=CC=1C1=CC=CC=C1 FKGARMNFEGUUFP-UHFFFAOYSA-N 0.000 claims 1
- WWYLDLGCYXVKMB-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound FC1=CC=CC=C1CNC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 WWYLDLGCYXVKMB-UHFFFAOYSA-N 0.000 claims 1
- QBRLCNKHXUBHAE-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound FC1=CC=CC(CNC(=O)NC=2C=CC(=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 QBRLCNKHXUBHAE-UHFFFAOYSA-N 0.000 claims 1
- HRYWBCMSSNOADX-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound C1=CC(F)=CC=C1CNC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 HRYWBCMSSNOADX-UHFFFAOYSA-N 0.000 claims 1
- YPFPNZZYSFPALS-UHFFFAOYSA-N 1-[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 YPFPNZZYSFPALS-UHFFFAOYSA-N 0.000 claims 1
- NMSLZKLSGJOACM-UHFFFAOYSA-N 1-[3-[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]phenyl]ethanol Chemical compound CC(O)C1=CC=CC(NCC=2C=C(C=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 NMSLZKLSGJOACM-UHFFFAOYSA-N 0.000 claims 1
- DHOBCFVLDNCPTP-UHFFFAOYSA-N 1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]-n-(thiophen-2-ylmethyl)methanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNCC1=CC=CS1 DHOBCFVLDNCPTP-UHFFFAOYSA-N 0.000 claims 1
- GAWDCFGDCVYXBM-UHFFFAOYSA-N 1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]-n-[[4-(trifluoromethyl)phenyl]methyl]methanamine Chemical compound C1=CC(C(F)(F)F)=CC=C1CNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 GAWDCFGDCVYXBM-UHFFFAOYSA-N 0.000 claims 1
- LLUCABACISDVEJ-UHFFFAOYSA-N 1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=CC=NC2=C1C=CN2 LLUCABACISDVEJ-UHFFFAOYSA-N 0.000 claims 1
- DKMSFKYTBAROMV-UHFFFAOYSA-N 1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=NC2=C1C=CN2 DKMSFKYTBAROMV-UHFFFAOYSA-N 0.000 claims 1
- IFKSPAFRVINCAT-UHFFFAOYSA-N 1-[4-(3-acetyl-1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]ethanone Chemical compound C=12C(C(=O)C)=CNC2=NC=CC=1C1=CC=C(C(C)=O)C=C1 IFKSPAFRVINCAT-UHFFFAOYSA-N 0.000 claims 1
- HUXNFPXNPZRJJH-UHFFFAOYSA-N 1-[4-(3-bromo-1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=NC2=C1C(Br)=CN2 HUXNFPXNPZRJJH-UHFFFAOYSA-N 0.000 claims 1
- HSZBXOYNPSAUKY-UHFFFAOYSA-N 1-[4-(3-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=NC2=C1C(Cl)=CN2 HSZBXOYNPSAUKY-UHFFFAOYSA-N 0.000 claims 1
- KAPNVDSMXCLCAD-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)-1h-pyrrolo[2,3-b]pyridin-3-yl]ethanone Chemical compound C=12C(C(=O)C)=CNC2=NC=CC=1C1=CC=CC(F)=C1 KAPNVDSMXCLCAD-UHFFFAOYSA-N 0.000 claims 1
- CISPXNYVLLQSNH-UHFFFAOYSA-N 1-[5-(1h-pyrrolo[2,3-b]pyridin-4-yl)thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC=C1C1=CC=NC2=C1C=CN2 CISPXNYVLLQSNH-UHFFFAOYSA-N 0.000 claims 1
- LCVHPHMVSRORGH-UHFFFAOYSA-N 1-[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1CC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 LCVHPHMVSRORGH-UHFFFAOYSA-N 0.000 claims 1
- XYBBXNCSGCKWCF-UHFFFAOYSA-N 1-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]piperidin-3-ol Chemical compound C1C(O)CCCN1CC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 XYBBXNCSGCKWCF-UHFFFAOYSA-N 0.000 claims 1
- MSAXTWFJXYJJPF-UHFFFAOYSA-N 1-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 MSAXTWFJXYJJPF-UHFFFAOYSA-N 0.000 claims 1
- CGNCOVJZQRWUQN-UHFFFAOYSA-N 1-benzyl-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1NC(=O)NCC1=CC=CC=C1 CGNCOVJZQRWUQN-UHFFFAOYSA-N 0.000 claims 1
- LEADQZKZEFERGP-UHFFFAOYSA-N 1-phenyl-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]urea Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1NC(=O)NC1=CC=CC=C1 LEADQZKZEFERGP-UHFFFAOYSA-N 0.000 claims 1
- BOICEQGQSYCYMH-UHFFFAOYSA-N 1-phenyl-n-[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=CC=1CNC(C)C1=CC=CC=C1 BOICEQGQSYCYMH-UHFFFAOYSA-N 0.000 claims 1
- MSYBXEOBAGBLFM-UHFFFAOYSA-N 1-phenyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNC(C)C1=CC=CC=C1 MSYBXEOBAGBLFM-UHFFFAOYSA-N 0.000 claims 1
- AOALFLLKUJAMFJ-UHFFFAOYSA-N 1-phenyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]methanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNCC1=CC=CC=C1 AOALFLLKUJAMFJ-UHFFFAOYSA-N 0.000 claims 1
- LVRUNIIPCOTYHD-UHFFFAOYSA-N 2-(2-fluorophenyl)-n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound FC1=CC=CC=C1CC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 LVRUNIIPCOTYHD-UHFFFAOYSA-N 0.000 claims 1
- SXIWZYNHPANAFR-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound FC1=CC=CC(CC(=O)NC=2C=CC(=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 SXIWZYNHPANAFR-UHFFFAOYSA-N 0.000 claims 1
- NHHCELHSUFIGDY-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 NHHCELHSUFIGDY-UHFFFAOYSA-N 0.000 claims 1
- NMSIBJORXPUOKW-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C1=CC(F)=CC=C1CCNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 NMSIBJORXPUOKW-UHFFFAOYSA-N 0.000 claims 1
- VZLDENCJUJTIHH-UHFFFAOYSA-N 2-(diethylamino)ethyl 4-[[5-(1h-pyrrolo[2,3-b]pyridin-4-yl)thiophen-2-yl]methylamino]benzoate Chemical compound C1=CC(C(=O)OCCN(CC)CC)=CC=C1NCC1=CC=C(C=2C=3C=CNC=3N=CC=2)S1 VZLDENCJUJTIHH-UHFFFAOYSA-N 0.000 claims 1
- ZNUDSRAYSAUSTH-UHFFFAOYSA-N 2-[4-[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1CC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 ZNUDSRAYSAUSTH-UHFFFAOYSA-N 0.000 claims 1
- YUVNZXDNPNDKBN-UHFFFAOYSA-N 2-[4-[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]phenyl]ethanol Chemical compound C1=CC(CCO)=CC=C1NCC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 YUVNZXDNPNDKBN-UHFFFAOYSA-N 0.000 claims 1
- GUMSTTBZAFRUKD-UHFFFAOYSA-N 2-[4-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1CC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 GUMSTTBZAFRUKD-UHFFFAOYSA-N 0.000 claims 1
- YVHWYZNRVTVJDU-UHFFFAOYSA-N 2-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]-3,4-dihydro-1h-isoquinoline Chemical compound C1CC2=CC=CC=C2CN1CC(C=C1)=CC=C1C1=CC=NC2=C1C=CN2 YVHWYZNRVTVJDU-UHFFFAOYSA-N 0.000 claims 1
- LNGQWTMTMCADTF-UHFFFAOYSA-N 2-[[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]methyl]cyclohexan-1-ol Chemical compound OC1CCCCC1CNCC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 LNGQWTMTMCADTF-UHFFFAOYSA-N 0.000 claims 1
- UQRXSSFJRSKQRP-UHFFFAOYSA-N 2-[[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]methyl]cyclohexan-1-ol Chemical compound OC1CCCCC1CNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 UQRXSSFJRSKQRP-UHFFFAOYSA-N 0.000 claims 1
- QRDPXMWBRFYGCJ-UHFFFAOYSA-N 2-[butyl-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]amino]ethanol Chemical compound C1=CC(CN(CCO)CCCC)=CC=C1C1=CC=NC2=C1C=CN2 QRDPXMWBRFYGCJ-UHFFFAOYSA-N 0.000 claims 1
- BNRZNIOJUKNFIO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C1=CC(CN(CCOC)CCOC)=CC=C1C1=CC=NC2=C1C=CN2 BNRZNIOJUKNFIO-UHFFFAOYSA-N 0.000 claims 1
- ARECOFLAJIWPKR-UHFFFAOYSA-N 2-methoxy-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C1=CC(CNCCOC)=CC=C1C1=CC=NC2=C1C=CN2 ARECOFLAJIWPKR-UHFFFAOYSA-N 0.000 claims 1
- CDPVVKRHEHNESI-UHFFFAOYSA-N 2-methyl-3-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]phenol Chemical compound CC1=C(O)C=CC=C1NCC1=CC=C(C=2C=3C=CNC=3N=CC=2)C=C1 CDPVVKRHEHNESI-UHFFFAOYSA-N 0.000 claims 1
- XDQIWAHXYZZLKB-UHFFFAOYSA-N 2-phenyl-n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1NC(=O)CC1=CC=CC=C1 XDQIWAHXYZZLKB-UHFFFAOYSA-N 0.000 claims 1
- RGBVBBZZZQWGOJ-UHFFFAOYSA-N 2-phenyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]acetamide Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNC(=O)CC1=CC=CC=C1 RGBVBBZZZQWGOJ-UHFFFAOYSA-N 0.000 claims 1
- AOGGPHNNNOAVJW-UHFFFAOYSA-N 2-phenyl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]propan-2-amine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNC(C)(C)C1=CC=CC=C1 AOGGPHNNNOAVJW-UHFFFAOYSA-N 0.000 claims 1
- BKCYYMMFJAYTHP-UHFFFAOYSA-N 2-pyridin-2-yl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNCCC1=CC=CC=N1 BKCYYMMFJAYTHP-UHFFFAOYSA-N 0.000 claims 1
- VOPHLJYKEMJYCJ-UHFFFAOYSA-N 2-pyrrolidin-1-yl-n-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]ethanamine Chemical compound C=1C=C(C=2C=3C=CNC=3N=CC=2)C=CC=1CNCCN1CCCC1 VOPHLJYKEMJYCJ-UHFFFAOYSA-N 0.000 claims 1
- GYMVBQOXLVVBRX-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)-n-[[5-(1h-pyrrolo[2,3-b]pyridin-4-yl)furan-2-yl]methyl]propan-1-amine Chemical compound C1CN(C)CCN1CCCNCC1=CC=C(C=2C=3C=CNC=3N=CC=2)O1 GYMVBQOXLVVBRX-UHFFFAOYSA-N 0.000 claims 1
- GAHIWVXJAFVSCV-UHFFFAOYSA-N 3-[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]benzamide Chemical compound NC(=O)C1=CC=CC(NCC=2C=C(C=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 GAHIWVXJAFVSCV-UHFFFAOYSA-N 0.000 claims 1
- ZASNOVPELXAJLV-UHFFFAOYSA-N 3-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NCC=2C=CC(=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 ZASNOVPELXAJLV-UHFFFAOYSA-N 0.000 claims 1
- QGMZIRDBBIYJKQ-UHFFFAOYSA-N 3-[[5-(1h-pyrrolo[2,3-b]pyridin-4-yl)thiophen-2-yl]methylamino]benzamide Chemical compound NC(=O)C1=CC=CC(NCC=2SC(=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 QGMZIRDBBIYJKQ-UHFFFAOYSA-N 0.000 claims 1
- OSDTVFJKHNSQMM-UHFFFAOYSA-N 3-amino-n-[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]propanamide Chemical compound NCCC(=O)NCC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 OSDTVFJKHNSQMM-UHFFFAOYSA-N 0.000 claims 1
- LWHMRDLIGBHBKL-UHFFFAOYSA-N 3-bromo-4-(4-ethenylphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C=12C(Br)=CNC2=NC=CC=1C1=CC=C(C=C)C=C1 LWHMRDLIGBHBKL-UHFFFAOYSA-N 0.000 claims 1
- ZSMRIWSMVPTAQV-UHFFFAOYSA-N 3-bromo-4-(4-phenylphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C=12C(Br)=CNC2=NC=CC=1C(C=C1)=CC=C1C1=CC=CC=C1 ZSMRIWSMVPTAQV-UHFFFAOYSA-N 0.000 claims 1
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| MY179032A (en) | 2004-10-25 | 2020-10-26 | Cancer Research Tech Ltd | Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors |
| JP2008545660A (ja) * | 2005-05-20 | 2008-12-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼ阻害剤として有用なピロロピリジン化合物 |
| HUE028588T2 (hu) | 2005-12-13 | 2016-12-28 | Incyte Holdings Corp | Heteroaril-szubsztituált pirrolo[2,3-b]piridinek és pirrolo[2,3-b]pirimidinek mint Janus-kináz inhibitorok |
| WO2007125321A2 (en) | 2006-04-25 | 2007-11-08 | Astex Therapeutics Limited | Purine and deazapurine derivatives as pharmaceutical compounds |
| US8604031B2 (en) * | 2006-05-18 | 2013-12-10 | Mannkind Corporation | Intracellular kinase inhibitors |
| NZ623002A (en) | 2006-06-26 | 2015-08-28 | Akebia Therapeutics Inc | Prolyl hydroxylase inhibitors and methods of use |
| DE102006033140A1 (de) * | 2006-07-18 | 2008-01-24 | Merck Patent Gmbh | Aminoindazolharnstoffderivate |
| GB0617161D0 (en) * | 2006-08-31 | 2006-10-11 | Vernalis R&D Ltd | Enzyme inhibitors |
| PL2848610T3 (pl) * | 2006-11-15 | 2018-01-31 | Ym Biosciences Australia Pty | Inhibitory aktywności kinazy |
| AR064416A1 (es) * | 2006-12-21 | 2009-04-01 | Cancer Rec Tech Ltd | Derivados de purina, piridina y pirimidina condensadas con heterociclos, moduladores de pka y/o pkb, composiciones farmaceuticas que los contienen, y usos para el tratamiento de enfermedades hiperproliferativas. |
| EP2740731B1 (en) * | 2007-06-13 | 2016-03-23 | Incyte Holdings Corporation | Crystalline salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile |
| BRPI0818533B8 (pt) | 2007-10-11 | 2021-05-25 | Astrazeneca Ab | composto, composição farmacêutica, uso de um composto, e, processo para a preparação de um composto |
| US8173635B2 (en) | 2007-11-02 | 2012-05-08 | Vertex Pharmaceuticals Incorporated | Kinase inhibitors |
| JP2011506445A (ja) * | 2007-12-13 | 2011-03-03 | アムジエン・インコーポレーテツド | γ−セクレターゼ調節剤 |
| AU2009206775A1 (en) * | 2008-01-22 | 2009-07-30 | Merck Patent Gmbh | Protein kinase inhibitors and use thereof |
| UA106037C2 (uk) * | 2008-02-04 | 2014-07-25 | Мерк'Юрі Терап'Ютікс, Інк. | Модулятори ampk (амф-активованої протеїнкінази) |
| KR100979439B1 (ko) * | 2008-04-10 | 2010-09-02 | 한국화학연구원 | 신규 피라졸 및 벤즈옥사졸 치환된 피리딘 유도체 또는이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를유효성분으로 함유하는 이상세포 성장 질환의 예방 및치료용 약학적 조성물 |
| CL2009001152A1 (es) | 2008-05-13 | 2009-10-16 | Array Biopharma Inc | Compuestos derivados de n-(4-(cicloalquilo nitrogenado-1-il)-1h-pirrolo[2,3-b]piridin-3-il)amida, inhibidores de cinasa; proceso de preparacion; composicion farmaceutica; y su uso para el tratamiento de una enfermedad proliferativa. |
| CL2009001884A1 (es) * | 2008-10-02 | 2010-05-14 | Incyte Holdings Corp | Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco. |
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