JP2005539000A5 - - Google Patents
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- JP2005539000A5 JP2005539000A5 JP2004525405A JP2004525405A JP2005539000A5 JP 2005539000 A5 JP2005539000 A5 JP 2005539000A5 JP 2004525405 A JP2004525405 A JP 2004525405A JP 2004525405 A JP2004525405 A JP 2004525405A JP 2005539000 A5 JP2005539000 A5 JP 2005539000A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- halo
- pyridin
- alkoxy
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 125000005843 halogen group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- -1 —CF 3 Chemical group 0.000 claims 5
- FXXJRBVEYNARBS-UHFFFAOYSA-N 4-[[4-[4-[5-(6-methylpyridin-2-yl)-2-propan-2-yl-1h-imidazol-4-yl]pyridin-2-yl]phenyl]methyl]morpholine Chemical compound N1C(C(C)C)=NC(C=2C=C(N=CC=2)C=2C=CC(CN3CCOCC3)=CC=2)=C1C1=CC=CC(C)=N1 FXXJRBVEYNARBS-UHFFFAOYSA-N 0.000 claims 4
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 241000711549 Hepacivirus C Species 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- HEEWFRYQSLPADJ-UHFFFAOYSA-N 2-[2-tert-butyl-4-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]pyridin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C(C)(C)C)C=2C=C(N=CC=2)C=2C=CC(CN3CCCC3)=CC=2)=N1 HEEWFRYQSLPADJ-UHFFFAOYSA-N 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000018565 Hemochromatosis Diseases 0.000 claims 1
- 241000700721 Hepatitis B virus Species 0.000 claims 1
- 206010019728 Hepatitis alcoholic Diseases 0.000 claims 1
- 208000002260 Keloid Diseases 0.000 claims 1
- 206010023330 Keloid scar Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010027398 Mesenteric fibrosis Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
- 206010034665 Peritoneal fibrosis Diseases 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 208000007107 Stomach Ulcer Diseases 0.000 claims 1
- 206010052428 Wound Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- JTBSSXWFYSSVJP-UHFFFAOYSA-N [S].C1=CSC=N1 Chemical compound [S].C1=CSC=N1 JTBSSXWFYSSVJP-UHFFFAOYSA-N 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000002353 alcoholic hepatitis Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 201000005917 gastric ulcer Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 210000001117 keloid Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 230000009251 neurologic dysfunction Effects 0.000 claims 1
- 208000015015 neurological dysfunction Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0217751A GB0217751D0 (en) | 2002-07-31 | 2002-07-31 | Compounds |
| GB0314698A GB0314698D0 (en) | 2003-06-24 | 2003-06-24 | Compounds |
| PCT/EP2003/008496 WO2004013135A1 (en) | 2002-07-31 | 2003-07-29 | 2-phenylpyridin-4-yl derivatives as alk5 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005539000A JP2005539000A (ja) | 2005-12-22 |
| JP2005539000A5 true JP2005539000A5 (https=) | 2006-09-14 |
Family
ID=31497253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004525405A Pending JP2005539000A (ja) | 2002-07-31 | 2003-07-29 | Ａｌｋ５阻害剤としての２−フェニルピリジン−４−イル誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20050245520A1 (https=) |
| EP (1) | EP1539748A1 (https=) |
| JP (1) | JP2005539000A (https=) |
| AR (1) | AR040726A1 (https=) |
| AU (1) | AU2003260345A1 (https=) |
| TW (1) | TW200417547A (https=) |
| WO (1) | WO2004013135A1 (https=) |
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| UA80296C2 (en) * | 2002-09-06 | 2007-09-10 | Biogen Inc | Imidazolopyridines and methods of making and using the same |
| AU2003256003A1 (en) | 2002-09-18 | 2004-04-08 | Pfizer Products Inc. | Novel oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors |
| MXPA05002981A (es) | 2002-09-18 | 2005-06-22 | Pfizer Prod Inc | Nuevos compuestos de imidazol como inhibidores del factor de crecimiento transformante (tgf). |
| CA2497971A1 (en) | 2002-09-18 | 2004-04-01 | Pfizer Products Inc. | Triazole derivatives as transforming growth factor (tgf) inhibitors |
| EP1542995A1 (en) | 2002-09-18 | 2005-06-22 | Pfizer Products Inc. | Novel isothiazole and isoxazole compounds as transforming growth factor (tgf) inhibitors |
| CA2496295C (en) | 2002-09-18 | 2010-11-23 | Michael John Munchhof | Novels pyrazole compounds as transforming growth factor (tgf) inhibitors |
| CL2004000234A1 (es) * | 2003-02-12 | 2005-04-15 | Biogen Idec Inc | Compuestos derivados 3-(piridin-2-il)-4-heteroaril-pirazol sustituidos, antagonistas de aik5 y/o aik4; composicion farmaceutica y uso del compuesto en el tratamiento de desordenes fibroticos como esclerodermia, lupus nefritico, cicatrizacion de herid |
| PA8595001A1 (es) * | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
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Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9809869D0 (en) * | 1998-05-09 | 1998-07-08 | Medical Res Council | Inhibition of protein kinases |
| GB0007405D0 (en) * | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| GB0027987D0 (en) * | 2000-11-16 | 2001-01-03 | Smithkline Beecham Plc | Compounds |
| AU2002225730A1 (en) * | 2000-11-16 | 2002-05-27 | Smith Kline Beecham Corporation | Compounds |
| ATE291020T1 (de) * | 2001-02-02 | 2005-04-15 | Smithkline Beecham Corp | Pyrazolderivate gegen tgf überexprimierung |
| GB0102665D0 (en) * | 2001-02-02 | 2001-03-21 | Glaxo Group Ltd | Compounds |
| GB0217783D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Compounds |
-
2003
- 2003-07-29 EP EP03766385A patent/EP1539748A1/en not_active Withdrawn
- 2003-07-29 AU AU2003260345A patent/AU2003260345A1/en not_active Abandoned
- 2003-07-29 WO PCT/EP2003/008496 patent/WO2004013135A1/en not_active Ceased
- 2003-07-29 AR AR20030102722A patent/AR040726A1/es not_active Application Discontinuation
- 2003-07-29 US US10/522,969 patent/US20050245520A1/en not_active Abandoned
- 2003-07-29 TW TW092120588A patent/TW200417547A/zh unknown
- 2003-07-29 JP JP2004525405A patent/JP2005539000A/ja active Pending
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