JP2012510997A5 - - Google Patents
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- JP2012510997A5 JP2012510997A5 JP2011539524A JP2011539524A JP2012510997A5 JP 2012510997 A5 JP2012510997 A5 JP 2012510997A5 JP 2011539524 A JP2011539524 A JP 2011539524A JP 2011539524 A JP2011539524 A JP 2011539524A JP 2012510997 A5 JP2012510997 A5 JP 2012510997A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- phenyl
- lower alkyl
- substituted
- hydroxy
- 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 description 554
- 125000000217 alkyl group Chemical group 0.000 claims description 230
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 151
- 125000003545 alkoxy group Chemical group 0.000 claims description 114
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 89
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 82
- 150000005829 chemical entities Chemical class 0.000 claims description 76
- 125000005843 halogen group Chemical group 0.000 claims description 60
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- 150000002431 hydrogen Chemical class 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000004043 oxo group Chemical group O=* 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 230000000694 effects Effects 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 125000003107 substituted aryl group Chemical group 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 230000005764 inhibitory process Effects 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 12
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
- 125000006413 ring segment Chemical group 0.000 claims description 8
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 6
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 5
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 5
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 5
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 210000004027 cell Anatomy 0.000 claims description 4
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 208000004736 B-Cell Leukemia Diseases 0.000 claims description 3
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 230000000172 allergic effect Effects 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 206010020751 Hypersensitivity Diseases 0.000 claims description 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 230000007815 allergy Effects 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 2
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 2
- 241000894007 species Species 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 15
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- GJTCISBNEUPNTC-UHFFFAOYSA-N 6-(1h-indol-6-yl)-n-(4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=CC=2)=CN2C1=NC=C2 GJTCISBNEUPNTC-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- XSMSNFMDVXXHGJ-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 XSMSNFMDVXXHGJ-UHFFFAOYSA-N 0.000 claims 1
- ZDYFZDYOBPTZEK-UHFFFAOYSA-N 6-(4-fluoro-1h-indol-6-yl)-n-(4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C=1C=2NC=CC=2C(F)=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 ZDYFZDYOBPTZEK-UHFFFAOYSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000004460 dihydrobenzooxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- UEFJTJWCEGBWHT-UHFFFAOYSA-N n-(3-methoxy-4-morpholin-4-ylphenyl)-6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical class COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NC=CC3=NC=2)=CC=C1N1CCOCC1 UEFJTJWCEGBWHT-UHFFFAOYSA-N 0.000 claims 1
- CNFWOZRHVSKIHH-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 CNFWOZRHVSKIHH-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 2
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 2
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 2
- 108091008875 B cell receptors Proteins 0.000 description 1
- 206010038687 Respiratory distress Diseases 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- 230000010398 acute inflammatory response Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000037979 autoimmune inflammatory disease Diseases 0.000 description 1
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12058708P | 2008-12-08 | 2008-12-08 | |
| US61/120,587 | 2008-12-08 | ||
| US14051408P | 2008-12-23 | 2008-12-23 | |
| US61/140,514 | 2008-12-23 | ||
| US24097909P | 2009-09-09 | 2009-09-09 | |
| US61/240,979 | 2009-09-09 | ||
| PCT/US2009/006445 WO2010068257A1 (en) | 2008-12-08 | 2009-12-07 | Imidazopyrazine syk inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014095907A Division JP5832586B2 (ja) | 2008-12-08 | 2014-05-07 | イミダゾピラジンＳｙｋ阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012510997A JP2012510997A (ja) | 2012-05-17 |
| JP2012510997A5 true JP2012510997A5 (https=) | 2013-01-31 |
| JP5567587B2 JP5567587B2 (ja) | 2014-08-06 |
Family
ID=42242994
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011539524A Active JP5567587B2 (ja) | 2008-12-08 | 2009-12-07 | イミダゾピラジンＳｙｋ阻害剤 |
| JP2014095907A Active JP5832586B2 (ja) | 2008-12-08 | 2014-05-07 | イミダゾピラジンＳｙｋ阻害剤 |
| JP2015159313A Active JP6132445B2 (ja) | 2008-12-08 | 2015-08-12 | イミダゾピラジンＳｙｋ阻害剤 |
| JP2017047354A Withdrawn JP2017101090A (ja) | 2008-12-08 | 2017-03-13 | イミダゾピラジンＳｙｋ阻害剤 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014095907A Active JP5832586B2 (ja) | 2008-12-08 | 2014-05-07 | イミダゾピラジンＳｙｋ阻害剤 |
| JP2015159313A Active JP6132445B2 (ja) | 2008-12-08 | 2015-08-12 | イミダゾピラジンＳｙｋ阻害剤 |
| JP2017047354A Withdrawn JP2017101090A (ja) | 2008-12-08 | 2017-03-13 | イミダゾピラジンＳｙｋ阻害剤 |
Country Status (30)
| Country | Link |
|---|---|
| US (7) | US8455493B2 (https=) |
| EP (3) | EP2716157B1 (https=) |
| JP (4) | JP5567587B2 (https=) |
| KR (4) | KR20170013414A (https=) |
| CN (2) | CN104744476B (https=) |
| AU (1) | AU2009325132B2 (https=) |
| BR (1) | BRPI0922225B1 (https=) |
| CA (1) | CA2746023C (https=) |
| CL (1) | CL2011001360A1 (https=) |
| CO (1) | CO6390078A2 (https=) |
| CY (1) | CY1118377T1 (https=) |
| DK (1) | DK2716157T3 (https=) |
| EA (3) | EA201690111A1 (https=) |
| ES (2) | ES2590804T3 (https=) |
| HR (1) | HRP20161036T1 (https=) |
| HU (1) | HUE030427T2 (https=) |
| IL (3) | IL213365A (https=) |
| LT (1) | LT2716157T (https=) |
| MX (1) | MX2011006091A (https=) |
| NZ (1) | NZ593459A (https=) |
| PE (2) | PE20120058A1 (https=) |
| PL (2) | PL2716157T3 (https=) |
| PT (2) | PT2716157T (https=) |
| RS (1) | RS55055B1 (https=) |
| SG (1) | SG171991A1 (https=) |
| SI (2) | SI2373169T1 (https=) |
| SM (1) | SMT201600267B (https=) |
| TW (2) | TWI529172B (https=) |
| VN (1) | VN28228A1 (https=) |
| WO (1) | WO2010068257A1 (https=) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009102468A1 (en) | 2008-02-13 | 2009-08-20 | Cgi Pharmaceuticals, Inc. | 6-aryl-imidaz0[l, 2-a] pyrazine derivatives, method of making, and method of use thereof |
| PL2716157T3 (pl) | 2008-12-08 | 2017-06-30 | Gilead Connecticut, Inc. | Imidazopirazynowe inhibitory Syk |
| PE20120121A1 (es) | 2008-12-08 | 2012-02-20 | Gilead Connecticut Inc | Derivados de imidazopirazina como inhibidores de syk |
| US8450321B2 (en) | 2008-12-08 | 2013-05-28 | Gilead Connecticut, Inc. | 6-(1H-indazol-6-yl)-N-[4-(morpholin-4-yl)phenyl]imidazo-[1,2-A]pyrazin-8-amine, or a pharmaceutically acceptable salt thereof, as a SYK inhibitor |
| NZ598220A (en) * | 2009-08-17 | 2014-02-28 | Intellikine Llc | Heterocyclic compounds and uses thereof |
| AU2011226689B2 (en) | 2010-03-11 | 2016-09-01 | Kronos Bio, Inc. | Imidazopyridines Syk inhibitors |
| WO2012116237A2 (en) | 2011-02-23 | 2012-08-30 | Intellikine, Llc | Heterocyclic compounds and uses thereof |
| US9145391B2 (en) | 2011-05-10 | 2015-09-29 | Merck Sharp & Dohme Corp. | Bipyridylaminopyridines as Syk inhibitors |
| CA2834062A1 (en) | 2011-05-10 | 2012-11-15 | Merck Sharp & Dohme Corp. | Pyridyl aminopyridines as syk inhibitors |
| EP2706853B1 (en) | 2011-05-10 | 2017-06-14 | Merck Sharp & Dohme Corp. | Aminopyrimidines as syk inhibitors |
| US9216173B2 (en) | 2011-10-05 | 2015-12-22 | Merck Sharp & Dohme Corp. | 2-Pyridyl carboxamide-containing spleen tyrosine kinase (SYK) inhibitors |
| WO2013052391A1 (en) | 2011-10-05 | 2013-04-11 | Merck Sharp & Dohme Corp. | PHENYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (Syk) INHIBITORS |
| EP2763975B1 (en) | 2011-10-05 | 2016-04-06 | Merck Sharp & Dohme Corp. | 3-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
| AR090650A1 (es) | 2012-04-12 | 2014-11-26 | Alcon Res Ltd | Tratamiento para respuestas inflamatorias inducidas por microbios en el ojo |
| WO2013188856A1 (en) * | 2012-06-14 | 2013-12-19 | Gilead Connecticut, Inc. | Imidazopyrazine syk inhibitors |
| EP2863914B1 (en) | 2012-06-20 | 2018-10-03 | Merck Sharp & Dohme Corp. | Pyrazolyl derivatives as syk inhibitors |
| EP2863913B1 (en) | 2012-06-20 | 2018-09-12 | Merck Sharp & Dohme Corp. | Imidazolyl analogs as syk inhibitors |
| EP2863915B1 (en) | 2012-06-22 | 2017-12-06 | Merck Sharp & Dohme Corp. | SUBSTITUTED DIAZINE AND TRIAZINE SPLEEN TYROSINE KINASE (Syk) INHIBITORS |
| EP2863916B1 (en) | 2012-06-22 | 2018-07-18 | Merck Sharp & Dohme Corp. | Substituted pyridine spleen tyrosine kinase (syk) inhibitors |
| AU2013302617A1 (en) * | 2012-08-14 | 2015-02-05 | Gilead Calistoga Llc | Combination therapies for treating cancer |
| US9353066B2 (en) | 2012-08-20 | 2016-05-31 | Merck Sharp & Dohme Corp. | Substituted phenyl-Spleen Tyrosine Kinase (Syk) inhibitors |
| WO2014048065A1 (en) | 2012-09-28 | 2014-04-03 | Merck Sharp & Dohme Corp. | Triazolyl derivatives as syk inhibitors |
| EP2931281B1 (en) | 2012-12-12 | 2018-01-17 | Merck Sharp & Dohme Corp. | Amino-pyrimidine-containing spleen tyrosine kinase inhibitors |
| EP2934525B1 (en) | 2012-12-21 | 2019-05-08 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminopyridines as spleen tyrosine kinase inhibitors |
| WO2014176210A1 (en) | 2013-04-26 | 2014-10-30 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
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- 2013-04-23 US US13/868,971 patent/US8748607B2/en active Active
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2014
- 2014-05-07 JP JP2014095907A patent/JP5832586B2/ja active Active
- 2014-05-09 US US14/274,618 patent/US9120811B2/en active Active
- 2014-06-09 US US14/300,189 patent/US9212191B2/en active Active
- 2014-08-27 IL IL234326A patent/IL234326A/en not_active IP Right Cessation
- 2014-11-23 IL IL235837A patent/IL235837A0/en unknown
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2015
- 2015-08-12 JP JP2015159313A patent/JP6132445B2/ja active Active
- 2015-10-13 US US14/882,278 patent/US9796718B2/en active Active
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2016
- 2016-08-05 SM SM201600267T patent/SMT201600267B/it unknown
- 2016-08-17 HR HRP20161036TT patent/HRP20161036T1/hr unknown
- 2016-08-18 CY CY20161100814T patent/CY1118377T1/el unknown
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2017
- 2017-03-13 JP JP2017047354A patent/JP2017101090A/ja not_active Withdrawn
- 2017-09-28 US US15/719,399 patent/US20180086769A1/en not_active Abandoned
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