JP2021500340A5 - - Google Patents
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- JP2021500340A5 JP2021500340A5 JP2020521911A JP2020521911A JP2021500340A5 JP 2021500340 A5 JP2021500340 A5 JP 2021500340A5 JP 2020521911 A JP2020521911 A JP 2020521911A JP 2020521911 A JP2020521911 A JP 2020521911A JP 2021500340 A5 JP2021500340 A5 JP 2021500340A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- cycloalkyl
- membered
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 774
- -1 Amino, Thio Chemical class 0.000 claims description 395
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 177
- 150000001875 compounds Chemical class 0.000 claims description 165
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 144
- 150000003839 salts Chemical class 0.000 claims description 139
- 125000001424 substituent group Chemical group 0.000 claims description 125
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 122
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 117
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 87
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 86
- 125000005843 halogen group Chemical group 0.000 claims description 77
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 75
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 229910052799 carbon Inorganic materials 0.000 claims description 70
- 125000003545 alkoxy group Chemical group 0.000 claims description 69
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 68
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 66
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 58
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 50
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000001188 haloalkyl group Chemical group 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 30
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 29
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 25
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 25
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 21
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- HWNHQKGIFMHZHG-UHFFFAOYSA-N imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound NC(=O)c1cn2ccnc2cn1 HWNHQKGIFMHZHG-UHFFFAOYSA-N 0.000 claims description 20
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 19
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 19
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 125000002971 oxazolyl group Chemical group 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 10
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- JPJMLQRVGZBWPD-UHFFFAOYSA-N 2-methyl-1h-imidazol-5-amine Chemical compound CC1=NC=C(N)N1 JPJMLQRVGZBWPD-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002460 imidazoles Chemical class 0.000 claims description 3
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 2
- PEUPUKDBCPLDIH-UHFFFAOYSA-N 1,2,4-triazole Chemical group C1=NC=N[N]1 PEUPUKDBCPLDIH-UHFFFAOYSA-N 0.000 claims description 2
- OGBOTYGRYZDLMG-UHFFFAOYSA-N 1-fluoroethanol Chemical compound CC(O)F OGBOTYGRYZDLMG-UHFFFAOYSA-N 0.000 claims description 2
- XNHNGYRHGMXUMT-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-imidazol-5-amine Chemical compound NC1=CN=C(C(F)(F)F)N1 XNHNGYRHGMXUMT-UHFFFAOYSA-N 0.000 claims description 2
- WHCMFEVONKMBRP-UHFFFAOYSA-N 2-fluoro-2-hydroxypropanamide Chemical compound CC(O)(F)C(N)=O WHCMFEVONKMBRP-UHFFFAOYSA-N 0.000 claims description 2
- QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 claims description 2
- JQTMGOLZSBTZMS-UHFFFAOYSA-N 4-methylpiperazine-1-carbaldehyde Chemical compound CN1CCN(C=O)CC1 JQTMGOLZSBTZMS-UHFFFAOYSA-N 0.000 claims description 2
- NHKZYIMWHDQJLJ-UHFFFAOYSA-N 8-amino-3-[5-(3-amino-1,1,1-trifluoro-2-hydroxy-3-oxopropan-2-yl)-2-methylphenyl]-N-(2-hydroxy-2-methylpropyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CC1=C(C=C(C=C1)C(O)(C(N)=O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(=O)NCC(C)(C)O NHKZYIMWHDQJLJ-UHFFFAOYSA-N 0.000 claims description 2
- OTZYLQXEUUJHEZ-UHFFFAOYSA-N 8-amino-N-[(1-cyanocyclobutyl)methyl]-3-[2-methyl-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(=O)NCC1(CCC1)C#N OTZYLQXEUUJHEZ-UHFFFAOYSA-N 0.000 claims description 2
- XHCVERLASWIGCB-UHFFFAOYSA-N 8-amino-N-methyl-3-[2-methyl-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CNC(=O)C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)(F)F XHCVERLASWIGCB-UHFFFAOYSA-N 0.000 claims description 2
- YSUYZIDWVGPTQS-UHFFFAOYSA-N CC1=NC=C(C2=NC(N)=CN2)O1 Chemical compound CC1=NC=C(C2=NC(N)=CN2)O1 YSUYZIDWVGPTQS-UHFFFAOYSA-N 0.000 claims description 2
- YPHFXUYWGMCMJJ-UHFFFAOYSA-N CN1N=CC=C1C1=NC(N)=CN1 Chemical compound CN1N=CC=C1C1=NC(N)=CN1 YPHFXUYWGMCMJJ-UHFFFAOYSA-N 0.000 claims description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 17
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 10
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 6
- 150000003857 carboxamides Chemical class 0.000 claims 6
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006721 (C5-C10) heteroaryl (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000002355 alkine group Chemical group 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- GILIYJDBJZWGBG-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-ol Chemical compound CC(O)C(F)(F)F GILIYJDBJZWGBG-UHFFFAOYSA-N 0.000 claims 1
- MZAFTZDOCPPASU-FIBGUPNXSA-N 2-[3-[8-amino-6-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-(trideuteriomethyl)phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=C3N(N=C1)CCC3)C(=CN=2)C=1C=C(C=CC=1C([2H])([2H])[2H])C(C(F)(F)F)(C)O MZAFTZDOCPPASU-FIBGUPNXSA-N 0.000 claims 1
- 125000000033 alkoxyamino group Chemical group 0.000 claims 1
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
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| SI3697789T1 (sl) * | 2017-10-18 | 2022-04-29 | Incyte Corporation | Kondenzirani imidazolni derivati, substituirani s terciarnimi hidroksi skupinami, kot zaviralci PI3K-gama |
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Family Cites Families (112)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4269846A (en) | 1979-10-29 | 1981-05-26 | Usv Pharmaceutical Corporation | Heterocyclic compounds useful as anti-allergy agents |
| US5137876A (en) | 1990-10-12 | 1992-08-11 | Merck & Co., Inc. | Nucleoside antiviral and anti-inflammatory compounds and compositions and methods for using same |
| US5521184A (en) | 1992-04-03 | 1996-05-28 | Ciba-Geigy Corporation | Pyrimidine derivatives and processes for the preparation thereof |
| CN1152031C (zh) | 1998-08-11 | 2004-06-02 | 诺瓦提斯公司 | 具有血管生成抑制活性的异喹啉衍生物 |
| US6133031A (en) | 1999-08-19 | 2000-10-17 | Isis Pharmaceuticals Inc. | Antisense inhibition of focal adhesion kinase expression |
| GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0011092D0 (en) | 2000-05-08 | 2000-06-28 | Black James Foundation | Gastrin and cholecystokinin receptor ligands (III) |
| PL202623B1 (pl) | 2000-06-28 | 2009-07-31 | Smithkline Beecham Plc | Sposób wytwarzania drobno zmielonego preparatu substancji leczniczej, drobno zmielona substancja lecznicza wytworzona tym sposobem i zawierająca ją kompozycja farmaceutyczna |
| AU2002337142B2 (en) | 2001-09-19 | 2007-10-11 | Aventis Pharma S.A. | Indolizines as kinase protein inhibitors |
| FR2831536A1 (fr) | 2001-10-26 | 2003-05-02 | Aventis Pharma Sa | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de kdr |
| EP1441725A1 (en) | 2001-10-26 | 2004-08-04 | Aventis Pharmaceuticals Inc. | Benzimidazoles and analogues and their use as protein kinases inhibitors |
| TWI302836B (en) | 2001-10-30 | 2008-11-11 | Novartis Ag | Staurosporine derivatives as inhibitors of flt3 receptor tyrosine kinase activity |
| DE10207843A1 (de) | 2002-02-15 | 2003-09-04 | Schering Ag | Mikrolia-Inhibitoren zur Unterbrechung von Interleukin 12 und IFN-gamma vermittelten Immunreaktionen |
| PE20040522A1 (es) | 2002-05-29 | 2004-09-28 | Novartis Ag | Derivados de diarilurea dependientes de la cinasa de proteina |
| GB0215676D0 (en) | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| AR042052A1 (es) | 2002-11-15 | 2005-06-08 | Vertex Pharma | Diaminotriazoles utiles como inhibidores de proteinquinasas |
| UA80767C2 (en) | 2002-12-20 | 2007-10-25 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
| US7186832B2 (en) * | 2003-02-20 | 2007-03-06 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| US7157460B2 (en) | 2003-02-20 | 2007-01-02 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| US8524899B2 (en) | 2003-03-04 | 2013-09-03 | California Institute Of Technology | Alternative heterocycles for DNA recognition |
| GB0305929D0 (en) | 2003-03-14 | 2003-04-23 | Novartis Ag | Organic compounds |
| CN1829709A (zh) | 2003-08-01 | 2006-09-06 | 健亚生物科技公司 | 对抗黄病毒的双环咪唑衍生物 |
| PE20050952A1 (es) | 2003-09-24 | 2005-12-19 | Novartis Ag | Derivados de isoquinolina como inhibidores de b-raf |
| AR046337A1 (es) * | 2003-10-15 | 2005-12-07 | Osi Pharm Inc | Imidazopirazina inhibidoras de las tirosinquinasas |
| WO2005118580A2 (en) | 2004-05-12 | 2005-12-15 | The Government Of The United States Of America As Represented By The Secretary, Department Of Health | Tricyclic compounds as inhibitors of the hypoxic signaling pathway |
| BRPI0511978A (pt) | 2004-06-10 | 2008-01-22 | Irm Llc | compostos e composições como inibidores de proteìnas quinases |
| JP2008520612A (ja) | 2004-11-24 | 2008-06-19 | ノバルティス アクチエンゲゼルシャフト | ＪＡＫ阻害剤およびＢｃｒ−Ａｂｌ、Ｆｌｔ−３、ＦＡＫまたはＲＡＦキナーゼ阻害剤のうち少なくとも１個の組合せ |
| ES2397275T3 (es) | 2005-08-04 | 2013-03-05 | Sirtris Pharmaceuticals, Inc. | Derivados de imidazopiridina como agentes moduladores de la sirtuína |
| TW200800213A (en) | 2005-09-02 | 2008-01-01 | Abbott Lab | Novel imidazo based heterocycles |
| ATE456565T1 (de) | 2006-06-22 | 2010-02-15 | Biovitrum Ab Publ | Pyridin- und pyrazinderivate als mnk- kinaseinhibitoren |
| WO2009005551A2 (en) | 2007-03-27 | 2009-01-08 | Paratek Pharmaceuticals, Inc. | Transcription factor modulating compounds and methods of use thereof |
| DE102007035333A1 (de) | 2007-07-27 | 2009-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel |
| GB0716292D0 (en) | 2007-08-21 | 2007-09-26 | Biofocus Dpi Ltd | Imidazopyrazine compounds |
| BRPI0820544A2 (pt) | 2007-11-16 | 2015-06-16 | Incyte Corp | 4-pirazolil-n-arilpirimidin-2-aminas e pirazolil-n-heteroarilpirimidin-2-aminas como inibidores de janus cinase |
| EP2234486A4 (en) | 2007-12-19 | 2011-09-14 | Scripps Research Inst | BENZIMIDAZOLES AND ANALOGS AS INHIBITORS OF RHO-KINASE |
| KR20100113500A (ko) | 2008-01-15 | 2010-10-21 | 시가 테크놀로지스, 인크. | 아레나바이러스 감염 치료용 항바이러스 약물 |
| WO2009108546A1 (en) | 2008-02-26 | 2009-09-03 | Merck & Co., Inc. | Ahcy hydrolase inhibitors for treatment of hyper homocysteinemia |
| ES2602577T3 (es) | 2008-03-11 | 2017-02-21 | Incyte Holdings Corporation | Derivados de azetidina y ciclobutano como inhibidores de JAK |
| AR071523A1 (es) | 2008-04-30 | 2010-06-23 | Merck Serono Sa | Compuestos biciclicos fusionados, un proceso para su preparacion, el compuesto para ser utilizado como medicamento en el tratamiento y profilaxis de enfermedades, una composicion farmaceutica y un conjunto que comprende paquetes separados del compuesto y de un ingrediente activo del medicamento |
| CA2763536C (en) | 2008-05-30 | 2017-05-09 | Marvin J. Miller | Anti-bacterial agents from benzo[d]heterocyclic scaffolds for prevention and treatment of multidrug resistant bacteria |
| US8470819B2 (en) | 2008-11-03 | 2013-06-25 | Merck Sharp & Dohme Corp. | Benzimidazole and aza-benzimidazole carboxamides |
| TW201028399A (en) | 2008-11-27 | 2010-08-01 | Shionogi & Co | Pyrimidine derivative and pyridine derivative both having pi3k inhibitory activity |
| GB0822981D0 (en) | 2008-12-17 | 2009-01-21 | Summit Corp Plc | Compounds for treatment of duchenne muscular dystrophy |
| EP2401273A1 (en) | 2009-02-27 | 2012-01-04 | Vertex Pharmaceuticals Incorporated | Tri-cyclic pyrazolopyridine kinase inhibitors |
| WO2010119264A1 (en) * | 2009-04-16 | 2010-10-21 | Centro Nacional De Investigaciones Oncólogicas (Cnio) | Imidazopyrazines for use as kinase inhibitors |
| ES2487542T3 (es) | 2009-05-22 | 2014-08-21 | Incyte Corporation | Derivados de N-(hetero)aril-pirrolidina de pirazol-4-il-pirrolo[2,3-d]pirimidinas y pirrol-3-il-pirrolo[2,3-d]pirimidinas como inhibidores de cinasas Janus |
| PE20120493A1 (es) | 2009-06-29 | 2012-05-20 | Incyte Corp | Pirimidinonas como inhibidores de pi3k |
| WO2011028685A1 (en) | 2009-09-01 | 2011-03-10 | Incyte Corporation | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| TW201130842A (en) | 2009-12-18 | 2011-09-16 | Incyte Corp | Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors |
| WO2011099832A2 (en) | 2010-02-12 | 2011-08-18 | Crystalgenomics, Inc. | Novel benzimidazole compound, preparation method thereof and pharmaceutical composition comprising the same |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| SMT201800137T1 (it) | 2010-03-10 | 2018-07-17 | Incyte Holdings Corp | Derivati di piperidin-4-il azetidina come inibitori di jak1 |
| US20130018039A1 (en) | 2010-03-31 | 2013-01-17 | Bodmer Vera Q | Imidazolyl-imidazoles as kinase inhibitors |
| AR081823A1 (es) | 2010-04-14 | 2012-10-24 | Incyte Corp | DERIVADOS FUSIONADOS COMO INHIBIDORES DE PI3Kd |
| WO2011149856A1 (en) | 2010-05-24 | 2011-12-01 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| WO2011149874A2 (en) | 2010-05-26 | 2011-12-01 | Schering Corporation | N-phenyl imidazole carboxamide inhibitors of 3-phosphoinositide-dependent protein kinase-1 |
| WO2011163195A1 (en) | 2010-06-21 | 2011-12-29 | Incyte Corporation | Fused pyrrole derivatives as pi3k inhibitors |
| PE20141044A1 (es) | 2010-10-13 | 2014-09-07 | Millennium Pharm Inc | Heteroarilos y sus usos |
| ES2536415T3 (es) | 2010-11-19 | 2015-05-25 | Incyte Corporation | Pirrolopiridinas y pirrolopirimidinas sustituidas heterocíclicas como inhibidores de JAK |
| SG190839A1 (en) | 2010-11-19 | 2013-07-31 | Incyte Corp | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| EA201390794A1 (ru) | 2010-11-30 | 2013-11-29 | Такеда Фармасьютикал Компани Лимитед | Бициклическое соединение |
| ES2764848T3 (es) | 2010-12-20 | 2020-06-04 | Incyte Holdings Corp | N-(1-(fenilo sustituido)etilo)-9H-purina-6-aminas como inhibidores de PI3K |
| WO2012125629A1 (en) | 2011-03-14 | 2012-09-20 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as pi3k inhibitors |
| US8673905B2 (en) | 2011-03-17 | 2014-03-18 | Hoffmann-La Roche Inc. | Imidazo pyrazines |
| WO2012135009A1 (en) | 2011-03-25 | 2012-10-04 | Incyte Corporation | Pyrimidine-4,6-diamine derivatives as pi3k inhibitors |
| KR102104125B1 (ko) | 2011-04-21 | 2020-05-29 | 재단법인 한국파스퇴르연구소 | 소염 화합물 |
| WO2012170867A1 (en) | 2011-06-09 | 2012-12-13 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of gpr-119 |
| WO2012177606A1 (en) | 2011-06-20 | 2012-12-27 | Incyte Corporation | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as jak inhibitors |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| KR20230038593A (ko) | 2011-09-02 | 2023-03-20 | 인사이트 홀딩스 코포레이션 | Ｐｉ３ｋ 억제제로서 헤테로시클릴아민 |
| EP2802586B1 (en) | 2012-01-10 | 2016-05-25 | Bayer Intellectual Property GmbH | Substituted imidazopyrazines as akt kinase inhibitors |
| US9212169B2 (en) | 2012-03-01 | 2015-12-15 | Hyogo College Of Medicine | Benzimidazole derivative and use thereof |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| WO2013173720A1 (en) | 2012-05-18 | 2013-11-21 | Incyte Corporation | Piperidinylcyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| BR112014029501B1 (pt) | 2012-05-31 | 2020-05-19 | Sumitomo Chemical Co | composto heterocíclico fundido, seu uso, agente de controle de pragas e método para o controle de pragas |
| ES2689429T3 (es) | 2012-07-13 | 2018-11-14 | Ucb Biopharma Sprl | Derivados de imidazopiridina como moduladores de actividad de TNF |
| US9181271B2 (en) | 2012-11-01 | 2015-11-10 | Incyte Holdings Corporation | Tricyclic fused thiophene derivatives as JAK inhibitors |
| TWI841376B (zh) | 2013-03-01 | 2024-05-01 | 美商英塞特控股公司 | 吡唑并嘧啶衍生物治療PI3Kδ相關病症之用途 |
| WO2014149207A2 (en) | 2013-03-15 | 2014-09-25 | Dow Agrosciences Llc | Benzimidazole-based insecticidal compositions and related methods |
| US8999992B2 (en) | 2013-03-15 | 2015-04-07 | Vm Pharma Llc | Crystalline forms of tryosine kinase inhibitors and their salts |
| EP2976077A4 (en) | 2013-03-22 | 2016-11-30 | Scripps Research Inst | SUBSTITUTED BENZIMIDAZOLE AS NOCICEPTIN RECEPTOR MODULATORS |
| EP2994142A4 (en) | 2013-05-08 | 2017-03-29 | Colorado Seminary, Which Owns and Operates The University of Denver | Antibiotic and anti-parasitic agents that modulate class ii fructose 1,6-bisphosphate aldolase |
| HRP20231048T1 (hr) | 2013-05-17 | 2023-12-22 | Incyte Holdings Corporation | Derivati bipirazola kao jak inhibitori |
| TWI641595B (zh) | 2013-07-17 | 2018-11-21 | 日商大塚製藥股份有限公司 | 氰基三唑化合物類 |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| MA39984B1 (fr) | 2014-04-08 | 2020-12-31 | Incyte Corp | Traitement d'affections malignes par lymphocytes b par un inhibiteur jak et pi3k combiné |
| EP2930048A1 (en) | 2014-04-10 | 2015-10-14 | Johnson Controls Automotive Electronics SAS | Head up display projecting visual information onto a screen |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| MX2017003464A (es) | 2014-09-16 | 2017-07-13 | Celgene Quanticel Res Inc | Inhibidores de histona desmetilasa. |
| WO2016064957A1 (en) * | 2014-10-22 | 2016-04-28 | Bristol-Myers Squibb Company | Bicyclic heteroaryl amine compounds as pi3k inhibitors |
| US10023576B2 (en) * | 2014-10-22 | 2018-07-17 | Bristol-Myers Squibb Company | Heteroaryl substituted pyrrolotriazine amine compounds as PI3K inhibitors |
| MA40933A (fr) | 2014-11-11 | 2017-09-19 | Piqur Therapeutics Ag | Difluorométhyl-aminopyridines et difluorométhyl-aminopyrimidines |
| WO2016106624A1 (en) * | 2014-12-31 | 2016-07-07 | Merck Sharp & Dohme Corp. | Tertiary alcohol imidazopyrazine btk inhibitors |
| WO2016130501A1 (en) | 2015-02-09 | 2016-08-18 | Incyte Corporation | Aza-heteroaryl compounds as pi3k-gamma inhibitors |
| US9968604B2 (en) | 2015-04-16 | 2018-05-15 | Chiesi Farmaceutici S.P.A. | Chromene derivatives as phoshoinositide 3-kinases inhibitors |
| AU2016261730A1 (en) | 2015-05-12 | 2017-11-16 | Zeno Royalties & Milestones, LLC | Bicyclic compounds |
| SI3371190T1 (sl) | 2015-11-06 | 2022-08-31 | Incyte Corporation | Heterociklične spojine kot inhibitorji PI3K gama |
| WO2017120194A1 (en) | 2016-01-05 | 2017-07-13 | Incyte Corporation | Pyridine and pyridimine compounds as pi3k-gamma inhibitors |
| WO2017223414A1 (en) | 2016-06-24 | 2017-12-28 | Incyte Corporation | HETEROCYCLIC COMPOUNDS AS PI3K-γ INHIBITORS |
| RU2019108464A (ru) | 2016-08-26 | 2020-09-28 | Мицубиси Танабе Фарма Корпорейшн | Бициклическое азотсодержащее гетероциклическое соединение |
| US20200000713A1 (en) | 2017-01-20 | 2020-01-02 | Massachusetts Institute Of Technology | Injectable polymer micro-depots for controlled local drug delivery |
| TWI674261B (zh) | 2017-02-17 | 2019-10-11 | 美商英能腫瘤免疫股份有限公司 | Nlrp3 調節劑 |
| RS65492B1 (sr) | 2017-07-24 | 2024-05-31 | Novartis Ag | Jedinjenja i kompozicije za lečenje stanja povezanih sa aktivnošću nlrp |
| US10988454B2 (en) | 2017-09-14 | 2021-04-27 | Abbvie Overseas S.À.R.L. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| SI3697789T1 (sl) | 2017-10-18 | 2022-04-29 | Incyte Corporation | Kondenzirani imidazolni derivati, substituirani s terciarnimi hidroksi skupinami, kot zaviralci PI3K-gama |
| AU2018353122B2 (en) | 2017-10-18 | 2023-11-23 | Epizyme, Inc. | Amine-substituted heterocyclic compounds as EHMT2 inhibitors, salts thereof, and methods of synthesis thereof |
| SI3728271T1 (sl) | 2017-12-19 | 2023-01-31 | Turning Point Therapeutics, Inc. | Makrociklične spojine za zdravljenje bolezni |
| BR112020012566B1 (pt) | 2017-12-21 | 2024-03-05 | Basf Se | Composto da fórmula i, composição, método de combate ou controle de pragas invertebradas, método de proteção de plantas em crescimento contra ataque ou infestação por pragas invertebradas, semente revestida, e usos de um composto da fórmula i |
| LT3728254T (lt) | 2017-12-21 | 2023-05-10 | Boehringer Ingelheim International Gmbh | Naujieji benzilaminu pakeistieji piridopirimidinonai ir jų dariniai kaip sos1 inhibitoriai |
| CR20250050A (es) | 2018-09-05 | 2025-03-19 | Incyte Corp | Formas cristalinas de un inhibidor de fosfoinositida 3–quinasa (pi3k) (divisional 2021-0165) |
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