UA72615C2 - Imidazopyrimidine and triazolopyrimidine derivatives, a method for the preparation thereof, medicament based thereon - Google Patents
Imidazopyrimidine and triazolopyrimidine derivatives, a method for the preparation thereof, medicament based thereon Download PDFInfo
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- UA72615C2 UA72615C2 UA2002119418A UA2002119418A UA72615C2 UA 72615 C2 UA72615 C2 UA 72615C2 UA 2002119418 A UA2002119418 A UA 2002119418A UA 2002119418 A UA2002119418 A UA 2002119418A UA 72615 C2 UA72615 C2 UA 72615C2
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- alkyl
- substituent
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- optionally containing
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- 238000000034 method Methods 0.000 title claims description 32
- 239000003814 drug Substances 0.000 title description 7
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 5
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 37
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims description 205
- -1 morpholino, piperidino Chemical group 0.000 claims description 107
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 82
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 229910052736 halogen Inorganic materials 0.000 claims description 67
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
- 150000002367 halogens Chemical class 0.000 claims description 57
- 125000003277 amino group Chemical group 0.000 claims description 49
- 125000004429 atom Chemical group 0.000 claims description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 35
- 230000000694 effects Effects 0.000 claims description 31
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 15
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 15
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 15
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 8
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 8
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- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
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- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
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- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
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- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical class [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
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- 239000000126 substance Substances 0.000 claims description 4
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
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- CKIIJIDEWWXQEA-UHFFFAOYSA-N 2-(bromomethyl)-1,3-dioxolane Chemical compound BrCC1OCCO1 CKIIJIDEWWXQEA-UHFFFAOYSA-N 0.000 claims 2
- 229940126601 medicinal product Drugs 0.000 claims 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims 2
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
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- 125000001072 heteroaryl group Chemical group 0.000 abstract description 4
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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Application Number | Priority Date | Filing Date | Title |
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JP2000128870A JP2001302667A (ja) | 2000-04-28 | 2000-04-28 | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
PCT/EP2001/004357 WO2001083485A1 (en) | 2000-04-28 | 2001-04-17 | Imidazopyrimidine derivatives and triazolopyrimidine derivatives |
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Country Status (38)
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US (1) | US6911443B2 (de) |
EP (1) | EP1278750B1 (de) |
JP (2) | JP2001302667A (de) |
KR (1) | KR20030009456A (de) |
CN (1) | CN1263756C (de) |
AR (1) | AR033367A1 (de) |
AT (1) | ATE272639T1 (de) |
AU (1) | AU783043B2 (de) |
BG (1) | BG107166A (de) |
BR (1) | BR0110404A (de) |
CA (1) | CA2407531A1 (de) |
CZ (1) | CZ20023551A3 (de) |
DE (1) | DE60104671T2 (de) |
DK (1) | DK1278750T3 (de) |
DO (1) | DOP2001000151A (de) |
EE (1) | EE200200606A (de) |
ES (1) | ES2225546T3 (de) |
HK (1) | HK1058362A1 (de) |
HR (1) | HRP20020943A2 (de) |
HU (1) | HUP0300846A2 (de) |
IL (1) | IL151919A0 (de) |
MA (1) | MA25746A1 (de) |
MX (1) | MXPA02010579A (de) |
MY (1) | MY141578A (de) |
NO (1) | NO20025154D0 (de) |
NZ (2) | NZ526221A (de) |
PE (1) | PE20011287A1 (de) |
PL (1) | PL358106A1 (de) |
PT (1) | PT1278750E (de) |
RU (1) | RU2306313C2 (de) |
SI (1) | SI1278750T1 (de) |
SK (1) | SK15332002A3 (de) |
SV (1) | SV2001000416A (de) |
TR (1) | TR200402300T4 (de) |
TW (1) | TWI222974B (de) |
UA (1) | UA72615C2 (de) |
WO (1) | WO2001083485A1 (de) |
ZA (1) | ZA200207676B (de) |
Families Citing this family (76)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2278016T3 (es) | 2001-04-09 | 2007-08-01 | Novartis Vaccines And Diagnostics, Inc. | Compuestos guanidino como agonistas del receptor de melanocortina 4 (mc4-r). |
PT1471057E (pt) | 2003-04-25 | 2006-05-31 | Actimis Pharmaceuticals Inc | Derivados de acido pirimidinilacetico uteis para o tratamento de doencas mediadas por crth2 |
JPWO2005037837A1 (ja) * | 2003-10-17 | 2006-12-28 | 日本化薬株式会社 | 置換2−アミノ−[1,2,4]トリアゾロ[1,5−a]ピリミジン誘導体及びその用途 |
JP2007514759A (ja) | 2003-12-19 | 2007-06-07 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
PT1718649E (pt) * | 2004-01-31 | 2009-08-06 | Actimis Pharmaceuticals Inc | Derivados de ácido imidazo[1,2-c]pirimidinilacético |
EP1765825A1 (de) * | 2004-06-25 | 2007-03-28 | Amgen Inc. | Zur behandlung von durch cytokine vermittelten krankheiten und anderen krankheiten geeignete kondensierte triazole und indazole |
WO2006023931A2 (en) | 2004-08-18 | 2006-03-02 | Takeda San Diego, Inc. | Kinase inhibitors |
US7754747B2 (en) | 2004-08-23 | 2010-07-13 | Wyeth Llc | Oxazolo-naphthyl acids |
WO2006044687A2 (en) * | 2004-10-15 | 2006-04-27 | Takeda San Diego, Inc. | Kinase inhibitors |
CA2599544A1 (en) | 2005-02-28 | 2006-09-08 | Japan Tobacco Inc. | Novel aminopyridine compound with syk inhibitory activity |
US7442700B2 (en) | 2005-07-01 | 2008-10-28 | Bristol-Myers Squibb Company | Pyrrolotriazine compounds useful as kinase inhibitors and methods of treating kinase-associated conditions therewith |
US8119655B2 (en) * | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
BRPI0617241A2 (pt) * | 2005-10-13 | 2016-11-08 | Glaxo Group Ltd | composto ou um sal ou solvato do mesmo, composição farmacêutica, método para tratar uma doença ou condição mediada por atividade syk inadequada em um mamífero, e, uso de um composto ou um sal ou solvato farmaceuticamente aceitável do mesmo |
CL2007002617A1 (es) * | 2006-09-11 | 2008-05-16 | Sanofi Aventis | Compuestos derivados de pirrolo[2,3-b]pirazin-6-ilo; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar inflamacion de las articulaciones, artritis reumatoide, tumores, linfoma de las celulas del manto. |
EP2223925A1 (de) * | 2006-10-09 | 2010-09-01 | Takeda Pharmaceutical Company Limited | Kinase-Inhibitoren |
GEP20135728B (en) | 2006-10-09 | 2013-01-25 | Takeda Pharmaceuticals Co | Kinase inhibitors |
LT3034075T (lt) * | 2006-11-22 | 2018-11-26 | Incyte Holdings Corporation | Imidazotriazinai ir imidazopirimidinai kaip kinazės inhibitoriai |
EP2123654A4 (de) | 2006-12-28 | 2011-05-11 | Taisho Pharmaceutical Co Ltd | Pyrazolopyrimidinverbindung |
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DE102008023801A1 (de) | 2008-05-15 | 2009-11-19 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Imidazo- und Triazolopyrimidine, Imidazo- und Pyrazolopyrazine und Imidazotriazine |
EP3123864A1 (de) | 2008-12-08 | 2017-02-01 | Gilead Connecticut, Inc. | Imidazopyrazin-syk-hemmer |
AU2009325133B2 (en) | 2008-12-08 | 2016-02-04 | Gilead Connecticut, Inc. | Imidazopyrazine Syk inhibitors |
JP5744859B2 (ja) * | 2009-06-15 | 2015-07-08 | ライジェル ファーマシューティカルズ, インコーポレイテッド | 脾臓チロシンキナーゼ(syk)の小分子阻害薬 |
CA2786950C (en) | 2009-12-23 | 2019-01-15 | Takeda Pharmaceutical Company Limited | Fused heteroaromatic pyrrolidinones as syk inhibitors |
AU2011226689B2 (en) * | 2010-03-11 | 2016-09-01 | Kronos Bio, Inc. | Imidazopyridines Syk inhibitors |
RU2012148246A (ru) * | 2010-04-14 | 2014-05-20 | Эррэй Биофарма Инк. | 5, 7- замещенные-имидазо[1, 2-с]пиримидины как ингибиторы jak-киназ |
AU2012253885A1 (en) | 2011-05-10 | 2013-10-31 | Merck Sharp & Dohme Corp. | Aminopyrimidines as Syk inhibitors |
WO2012154520A1 (en) | 2011-05-10 | 2012-11-15 | Merck Sharp & Dohme Corp. | Pyridyl aminopyridines as syk inhibitors |
US9145391B2 (en) | 2011-05-10 | 2015-09-29 | Merck Sharp & Dohme Corp. | Bipyridylaminopyridines as Syk inhibitors |
WO2012167423A1 (en) | 2011-06-08 | 2012-12-13 | Hutchison Medipharma Limited | Substituted pyridopyrazines as novel syk inhibitors |
EP2723739B1 (de) | 2011-06-22 | 2016-08-24 | Takeda Pharmaceutical Company Limited | Substituierte 6-aza-isoindolin-1-on-derivate |
US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
WO2013052393A1 (en) | 2011-10-05 | 2013-04-11 | Merck Sharp & Dohme Corp. | 3-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 |
WO2013052394A1 (en) | 2011-10-05 | 2013-04-11 | Merck Sharp & Dohme Corp. | 2-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
CN103987713A (zh) * | 2011-10-12 | 2014-08-13 | 阵列生物制药公司 | 5,7-取代的咪唑并[1,2-c]嘧啶 |
NZ627250A (en) * | 2011-12-28 | 2016-04-29 | Fujifilm Corp | Novel nicotinamide derivative or salt thereof |
US9242984B2 (en) | 2012-06-20 | 2016-01-26 | Merck Sharp & Dohme Corp. | Pyrazolyl derivatives as Syk inhibitors |
WO2013192128A1 (en) | 2012-06-20 | 2013-12-27 | Merck Sharp & Dohme Corp. | Imidazolyl analogs as syk inhibitors |
US9376418B2 (en) | 2012-06-22 | 2016-06-28 | Merck Sharp & Dohme Corp. | Substituted pyridine spleen tyrosine kinase (SYK) inhibitors |
WO2013192088A1 (en) | 2012-06-22 | 2013-12-27 | Merck Sharp & Dohme Corp. | SUBSTITUTED DIAZINE AND TRIAZINE SPLEEN TYROSINE KINASE (Syk) INHIBITORS |
US9353066B2 (en) | 2012-08-20 | 2016-05-31 | Merck Sharp & Dohme Corp. | Substituted phenyl-Spleen Tyrosine Kinase (Syk) inhibitors |
EP2900665B1 (de) | 2012-09-28 | 2018-01-03 | Merck Sharp & Dohme Corp. | Triazolylderivate als syk-hemmer |
EP2931281B1 (de) | 2012-12-12 | 2018-01-17 | Merck Sharp & Dohme Corp. | Aminopyridinhaltige milz-tyrosinkinase-hemmer |
WO2014100314A1 (en) | 2012-12-21 | 2014-06-26 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminopyridines as spleen tyrosine kinase inhibitors |
WO2014176216A1 (en) | 2013-04-26 | 2014-10-30 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminopyrimidines as spleen tyrosine kinase inhibitors |
US9745295B2 (en) | 2013-04-26 | 2017-08-29 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
UA115815C2 (uk) | 2013-07-30 | 2017-12-26 | Гіліад Коннектікут, Інк. | Склад на основі інгібіторів syk |
KR101810798B1 (ko) | 2013-07-30 | 2017-12-19 | 질레드 코네티컷 인코포레이티드 | Syk 억제제의 다형체 |
MX2016007311A (es) | 2013-12-04 | 2016-09-07 | Gilead Sciences Inc | Metodos para tratar canceres. |
WO2015094997A1 (en) | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
US9822107B2 (en) | 2013-12-20 | 2017-11-21 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
WO2015095444A1 (en) | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
TWI662037B (zh) | 2013-12-23 | 2019-06-11 | 美商基利科學股份有限公司 | 脾酪胺酸激酶抑制劑 |
US9290505B2 (en) | 2013-12-23 | 2016-03-22 | Gilead Sciences, Inc. | Substituted imidazo[1,2-a]pyrazines as Syk inhibitors |
EP3116506B1 (de) | 2014-03-13 | 2019-04-17 | Merck Sharp & Dohme Corp. | 2-pyrazincarboxamide als milz-tyrosinkinase-inhibitoren |
WO2015140054A1 (en) | 2014-03-19 | 2015-09-24 | Boehringer Ingelheim International Gmbh | Heteroaryl syk inhibitors |
NZ726365A (en) | 2014-07-14 | 2018-06-29 | Gilead Sciences Inc | Combinations for treating cancers |
EP3347353B1 (de) | 2015-09-11 | 2019-07-17 | Boehringer Ingelheim International GmbH | Pyrazolylsubstituierte heteroaryle und deren verwendung als medikamente |
AU2018321264A1 (en) | 2017-08-25 | 2020-02-27 | Kronos Bio, Inc. | Polymorphs of Syk inhibitors |
MX2020004155A (es) | 2017-10-19 | 2020-08-03 | Bayer Animal Health Gmbh | Uso de pirrolidonas heteroaromaticas fusionadas para el tratamiento y prevencion de enfermedades en animales. |
WO2019099578A1 (en) * | 2017-11-14 | 2019-05-23 | Chidren's Medical Center Corporation | Use of imidazopyrimidine for modulating human immune response |
KR20200088397A (ko) | 2017-11-14 | 2020-07-22 | 칠드런'즈 메디컬 센터 코포레이션 | 신규 이미다조피리미딘 화합물 및 그의 용도 |
WO2019235570A1 (ja) * | 2018-06-06 | 2019-12-12 | 富士フイルム株式会社 | グリオーマの処置剤および医薬組成物 |
WO2019235571A1 (ja) * | 2018-06-06 | 2019-12-12 | 富士フイルム株式会社 | 血液がんの処置剤および医薬組成物 |
WO2019235572A1 (ja) * | 2018-06-06 | 2019-12-12 | 富士フイルム株式会社 | 固形がんの処置剤および医薬組成物 |
WO2020092528A1 (en) | 2018-10-31 | 2020-05-07 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds having hpk1 inhibitory activity |
CN113227089B (zh) | 2018-10-31 | 2024-07-05 | 吉利德科学公司 | 作为hpk1抑制剂的取代的6-氮杂苯并咪唑化合物 |
CA3130848A1 (en) | 2019-02-22 | 2020-08-27 | Kronos Bio, Inc. | Solid forms of condensed pyrazines as syk inhibitors |
MX2021009863A (es) | 2019-03-21 | 2021-11-12 | Onxeo | Una molecula dbait en combinacion con inhibidor de quinasa para el tratamiento del cancer. |
TWI826690B (zh) | 2019-05-23 | 2023-12-21 | 美商基利科學股份有限公司 | 經取代之烯吲哚酮化物及其用途 |
KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
WO2021173476A1 (en) * | 2020-02-24 | 2021-09-02 | The Trustees Of Columbia University In The City Of New York | Compounds, pharmaceutical formulations, and methods for treatment of cancer |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4483987A (en) * | 1983-06-20 | 1984-11-20 | G. D. Searle & Co. | 8-Substituted 7-phenyl-1,2,4-triazolo[2,3-c]pyrimidines-5-amines and amides |
AU744939B2 (en) * | 1997-09-26 | 2002-03-07 | Merck & Co., Inc. | Novel angiogenesis inhibitors |
ATE401312T1 (de) * | 1997-12-15 | 2008-08-15 | Astellas Pharma Inc | Pyrimidin-5-carboxamid-derivate |
US6673564B2 (en) * | 1999-10-18 | 2004-01-06 | Millennium Pharmaceuticals, Inc. | Methods for using 22045, a human cyclic nucleotide phosphodiesterase |
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