JP2012525349A5 - - Google Patents
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- Publication number
- JP2012525349A5 JP2012525349A5 JP2012507720A JP2012507720A JP2012525349A5 JP 2012525349 A5 JP2012525349 A5 JP 2012525349A5 JP 2012507720 A JP2012507720 A JP 2012507720A JP 2012507720 A JP2012507720 A JP 2012507720A JP 2012525349 A5 JP2012525349 A5 JP 2012525349A5
- Authority
- JP
- Japan
- Prior art keywords
- oxazol
- methyl
- pharmaceutically acceptable
- acceptable salt
- pyridinyl
- 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
Links
- 150000003839 salts Chemical class 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 18
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 10
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 230000000694 effects Effects 0.000 claims 10
- 230000001404 mediated effect Effects 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- -1 —OR 6 Chemical group 0.000 claims 5
- MCIDWGZGWVSZMK-UHFFFAOYSA-N 2-[6-(1h-indol-4-yl)-1h-indazol-4-yl]-5-[(4-propan-2-ylpiperazin-1-yl)methyl]-1,3-oxazole Chemical compound C1CN(C(C)C)CCN1CC1=CN=C(C=2C=3C=NNC=3C=C(C=2)C=2C=3C=CNC=3C=CC=2)O1 MCIDWGZGWVSZMK-UHFFFAOYSA-N 0.000 claims 4
- 206010052779 Transplant rejections Diseases 0.000 claims 4
- NLUPPCTVKHDVIQ-GASCZTMLSA-N n-[5-[4-[5-[[(2r,6s)-2,6-dimethylmorpholin-4-yl]methyl]-1,3-oxazol-2-yl]-1h-indazol-6-yl]-2-methoxypyridin-3-yl]methanesulfonamide Chemical compound C1=C(NS(C)(=O)=O)C(OC)=NC=C1C1=CC(C=2OC(CN3C[C@@H](C)O[C@@H](C)C3)=CN=2)=C(C=NN2)C2=C1 NLUPPCTVKHDVIQ-GASCZTMLSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000002651 drug therapy Methods 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 2
- 208000004852 Lung Injury Diseases 0.000 claims 2
- 208000034486 Multi-organ failure Diseases 0.000 claims 2
- 208000010718 Multiple Organ Failure Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 206010062106 Respiratory tract infection viral Diseases 0.000 claims 2
- 206010069363 Traumatic lung injury Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 231100000515 lung injury Toxicity 0.000 claims 2
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 230000019100 sperm motility Effects 0.000 claims 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 2
- OYVPDRMOMRERQE-IYBDPMFKSA-N (2r,6s)-4-[[2-[6-(1h-indol-4-yl)-1h-indazol-4-yl]-1,3-oxazol-5-yl]methyl]-2,6-dimethylmorpholine Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC1=CN=C(C=2C=3C=NNC=3C=C(C=2)C=2C=3C=CNC=3C=CC=2)O1 OYVPDRMOMRERQE-IYBDPMFKSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- QGFMDPOUJANKPQ-UHFFFAOYSA-N 2-[6-(1h-indol-4-yl)-1h-indazol-4-yl]-5-(piperazin-1-ylmethyl)-1,3-oxazole Chemical compound C=1N=C(C=2C=3C=NNC=3C=C(C=2)C=2C=3C=CNC=3C=CC=2)OC=1CN1CCNCC1 QGFMDPOUJANKPQ-UHFFFAOYSA-N 0.000 claims 1
- QZDOSCAPAKUEMQ-UHFFFAOYSA-N 4-[[2-[6-(1h-indol-4-yl)-1h-indazol-4-yl]-1,3-oxazol-5-yl]methyl]morpholine Chemical compound C=1N=C(C=2C=3C=NNC=3C=C(C=2)C=2C=3C=CNC=3C=CC=2)OC=1CN1CCOCC1 QZDOSCAPAKUEMQ-UHFFFAOYSA-N 0.000 claims 1
- 201000002909 Aspergillosis Diseases 0.000 claims 1
- 208000036641 Aspergillus infections Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010066476 Haematological malignancy Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 230000005713 exacerbation Effects 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- LWCKBXWOANSAIZ-UHFFFAOYSA-N n-[2-methoxy-5-[4-[5-[(4-propan-2-ylpiperazin-1-yl)methyl]-1,3-oxazol-2-yl]-1h-indazol-6-yl]pyridin-3-yl]methanesulfonamide Chemical compound C1=C(NS(C)(=O)=O)C(OC)=NC=C1C1=CC(C=2OC(CN3CCN(CC3)C(C)C)=CN=2)=C(C=NN2)C2=C1 LWCKBXWOANSAIZ-UHFFFAOYSA-N 0.000 claims 1
- NLUPPCTVKHDVIQ-HUUCEWRRSA-N n-[5-[4-[5-[[(2r,6r)-2,6-dimethylmorpholin-4-yl]methyl]-1,3-oxazol-2-yl]-1h-indazol-6-yl]-2-methoxypyridin-3-yl]methanesulfonamide Chemical compound C1=C(NS(C)(=O)=O)C(OC)=NC=C1C1=CC(C=2OC(CN3C[C@@H](C)O[C@H](C)C3)=CN=2)=C(C=NN2)C2=C1 NLUPPCTVKHDVIQ-HUUCEWRRSA-N 0.000 claims 1
- XKTYUDPOFFQXQD-CALCHBBNSA-N n-[5-[4-[5-[[(2r,6s)-2,6-dimethylmorpholin-4-yl]methyl]-1,3-oxazol-2-yl]-1h-indazol-6-yl]-2-methoxypyridin-3-yl]-2,4-difluorobenzenesulfonamide Chemical compound COC1=NC=C(C=2C=C3NN=CC3=C(C=3OC(CN4C[C@@H](C)O[C@@H](C)C4)=CN=3)C=2)C=C1NS(=O)(=O)C1=CC=C(F)C=C1F XKTYUDPOFFQXQD-CALCHBBNSA-N 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 208000020017 viral respiratory tract infection Diseases 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17403309P | 2009-04-30 | 2009-04-30 | |
| US61/174,033 | 2009-04-30 | ||
| PCT/EP2010/055666 WO2010125082A1 (en) | 2009-04-30 | 2010-04-28 | Oxazole substituted indazoles as pi3-kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012525349A JP2012525349A (ja) | 2012-10-22 |
| JP2012525349A5 true JP2012525349A5 (enExample) | 2013-06-20 |
| JP5570589B2 JP5570589B2 (ja) | 2014-08-13 |
Family
ID=42225106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012507720A Active JP5570589B2 (ja) | 2009-04-30 | 2010-04-28 | Ｐｉ３キナーゼ阻害剤としてのオキサゾール置換インダゾール |
Country Status (39)
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2280705B1 (en) | 2008-06-05 | 2014-10-08 | Glaxo Group Limited | Novel compounds |
| ES2445199T3 (es) * | 2008-06-05 | 2014-02-28 | Glaxo Group Limited | Derivados de benzpirazol como inhibidores de PI3-quinasas |
| JP5502077B2 (ja) * | 2008-06-05 | 2014-05-28 | グラクソ グループ リミテッド | 新規な化合物 |
| US8524751B2 (en) | 2009-03-09 | 2013-09-03 | GlaxoSmithKline Intellecutual Property Development | 4-oxadiazol-2-YL-indazoles as inhibitors of P13 kinases |
| ES2644724T3 (es) | 2009-04-30 | 2017-11-30 | Glaxo Group Limited | Indazoles sustituidos con oxazol como inhibidores de PI3-cinasas |
| CN102372675B (zh) * | 2010-08-14 | 2013-12-18 | 王娜 | 6-氯-4-碘吲唑及其制备方法与应用 |
| US9102668B2 (en) | 2010-09-08 | 2015-08-11 | Glaxo Group Limited | Polymorphs and salts |
| JP5876051B2 (ja) * | 2010-09-08 | 2016-03-02 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | インフルエンザウィルス感染の治療に使用するためのインダゾール誘導体 |
| HUE026059T2 (en) | 2010-09-08 | 2016-05-30 | Glaxosmithkline Ip Dev Ltd | N- [5- [4- (5 - {[(2R, 6S) -2,6-dimethyl-4-morpholinyl] methyl} -1,3-oxazol-2-yl) -1H-indazol-6-yl ] Polymorphs and salts of 2 - (methyloxy) -3-pyridinyl] methanesulfonamide |
| GB201018124D0 (en) | 2010-10-27 | 2010-12-08 | Glaxo Group Ltd | Polymorphs and salts |
| AU2011326071A1 (en) * | 2010-11-08 | 2013-05-23 | Lycera Corporation | N- sulfonylated tetrahydroquinolines and related bicyclic compounds inhibition of RORy activity and the treatment of diseases |
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| EP2872143B1 (en) * | 2012-07-16 | 2017-12-13 | Neuropore Therapies, Inc. | Di-and tri-heteroaryl derivatives as inhibitors of protein aggregation |
| US20150258127A1 (en) | 2012-10-31 | 2015-09-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for preventing antiphospholipid syndrome (aps) |
| WO2014098232A1 (ja) * | 2012-12-21 | 2014-06-26 | Yamashita Chikamasa | Ｐｉ３キナーゼ阻害剤を含む医薬組成物、ビタミンｄ受容体に作用する化合物を含む医薬組成物、凍結乾燥組成物、凍結乾燥組成物の製造方法、及び経肺投与用医薬組成物 |
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| US20160263109A1 (en) * | 2013-10-17 | 2016-09-15 | Glaxosmithkline Intellectual Property Development Limited | P13k inhibitor for treatment of respiratory disease |
| WO2015095792A1 (en) | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Carbamate benzoxaxine propionic acids and acid derivatives for modulation of rorgamma activity and the treatment of disease |
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| US9127069B1 (en) * | 2014-06-11 | 2015-09-08 | Antecip Bioventures LLC | Compositions comprising rank/rankl antagonists and related compounds for treating pain |
| CN104086538B (zh) * | 2014-06-13 | 2016-07-06 | 南京药石科技股份有限公司 | 一种pi3k激酶抑制剂的中间体及其制备方法与应用 |
| WO2016059220A1 (en) | 2014-10-16 | 2016-04-21 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Tcr-activating agents for use in the treatment of t-all |
| CA2975997A1 (en) | 2015-02-11 | 2016-08-18 | Merck Sharp & Dohme Corp. | Substituted pyrazole compounds as rorgammat inhibitors and uses thereof |
| JP2018515491A (ja) | 2015-05-05 | 2018-06-14 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγの作動薬及び疾患の療法として使用するジヒドロ−２Ｈ−ベンゾ［ｂ］［１，４］オキサジンスルホンアミド及び関連化合物 |
| GB201509492D0 (en) * | 2015-06-02 | 2015-07-15 | Glaxosmithkline Ip Dev Ltd | Novel processes |
| EP3307738B1 (en) | 2015-06-11 | 2022-04-20 | The Regents of the University of Michigan | Aryl dihydro-2h-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of rory and the treatment of disease |
| CA3002846A1 (en) | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Substituted bicyclic pyrazole compounds as rorgammat inhibitors and uses thereof |
| WO2017075185A1 (en) | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Heteroaryl substituted benzoic acids as rorgammat inhibitors and uses thereof |
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