CA2575316A1 - Trifluoromethyl substituted benzamides as kinase inhibitors - Google Patents
Trifluoromethyl substituted benzamides as kinase inhibitors Download PDFInfo
- Publication number
- CA2575316A1 CA2575316A1 CA002575316A CA2575316A CA2575316A1 CA 2575316 A1 CA2575316 A1 CA 2575316A1 CA 002575316 A CA002575316 A CA 002575316A CA 2575316 A CA2575316 A CA 2575316A CA 2575316 A1 CA2575316 A1 CA 2575316A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- formula
- phenyl
- trifluoromethyl
- benzamide
- 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.)
- Abandoned
Links
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 title abstract description 7
- 150000003936 benzamides Chemical class 0.000 title abstract description 6
- 229940043355 kinase inhibitor Drugs 0.000 title description 6
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 6
- 229940054066 benzamide antipsychotics Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 296
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 80
- 238000000034 method Methods 0.000 claims abstract description 66
- 201000010099 disease Diseases 0.000 claims abstract description 64
- 238000011282 treatment Methods 0.000 claims abstract description 56
- 102000001253 Protein Kinase Human genes 0.000 claims abstract description 20
- 108060006633 protein kinase Proteins 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- 230000002062 proliferating effect Effects 0.000 claims abstract description 15
- 208000035475 disorder Diseases 0.000 claims abstract description 14
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
- 108091000080 Phosphotransferase Proteins 0.000 claims description 52
- 102000020233 phosphotransferase Human genes 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 230000005764 inhibitory process Effects 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 15
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 11
- 108060006706 SRC Proteins 0.000 claims description 10
- 102000001332 SRC Human genes 0.000 claims description 10
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 108010029869 Proto-Oncogene Proteins c-raf Proteins 0.000 claims description 9
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000001131 transforming effect Effects 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- IWGYXSFAZPPOMV-UHFFFAOYSA-N 4-methyl-n-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Chemical compound C1CN(C)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=C(C)C(B2OC(C)(C)C(C)(C)O2)=C1 IWGYXSFAZPPOMV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 3
- XWRIKTTXWRPZEP-UHFFFAOYSA-N 3-(1,3-benzothiazol-5-yl)-4-methyl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(C=2C=C3N=CSC3=CC=2)C(C)=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 XWRIKTTXWRPZEP-UHFFFAOYSA-N 0.000 claims description 2
- LKTXZPVKQYEMBU-UHFFFAOYSA-N 3-(1,3-benzothiazol-6-yl)-4-methyl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(C=2C=C3SC=NC3=CC=2)C(C)=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 LKTXZPVKQYEMBU-UHFFFAOYSA-N 0.000 claims description 2
- QJKQUQSBZCHWKL-UHFFFAOYSA-N 4-methyl-3-phthalazin-6-yl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(C=2C=C3C=NN=CC3=CC=2)C(C)=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 QJKQUQSBZCHWKL-UHFFFAOYSA-N 0.000 claims description 2
- DOOUPYSMBGVLED-UHFFFAOYSA-N 4-methyl-n-[4-(morpholin-4-ylmethyl)-3-(trifluoromethyl)phenyl]-3-phthalazin-6-ylbenzamide Chemical compound C1=C(C=2C=C3C=NN=CC3=CC=2)C(C)=CC=C1C(=O)NC(C=C1C(F)(F)F)=CC=C1CN1CCOCC1 DOOUPYSMBGVLED-UHFFFAOYSA-N 0.000 claims description 2
- 239000007819 coupling partner Substances 0.000 claims description 2
- HUEBBWXHQRJQBA-UHFFFAOYSA-N n-(4-methyl-3-phthalazin-6-ylphenyl)-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2C=C3C=NN=CC3=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 HUEBBWXHQRJQBA-UHFFFAOYSA-N 0.000 claims description 2
- JNANTAFLVVZBSS-UHFFFAOYSA-N n-(4-methyl-3-phthalazin-6-ylphenyl)-4-(morpholin-4-ylmethyl)-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2C=C3C=NN=CC3=CC=2)C(C)=CC=C1NC(=O)C(C=C1C(F)(F)F)=CC=C1CN1CCOCC1 JNANTAFLVVZBSS-UHFFFAOYSA-N 0.000 claims description 2
- PSRLFLMSZFBATQ-UHFFFAOYSA-N n-(4-methyl-3-phthalazin-6-ylphenyl)-4-(piperidin-1-ylmethyl)-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2C=C3C=NN=CC3=CC=2)C(C)=CC=C1NC(=O)C(C=C1C(F)(F)F)=CC=C1CN1CCCCC1 PSRLFLMSZFBATQ-UHFFFAOYSA-N 0.000 claims description 2
- ISHGNBGFTLNSCV-UHFFFAOYSA-N n-(4-methyl-3-phthalazin-6-ylphenyl)-4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(C(C)=CC=2)C=2C=C3C=NN=CC3=CC=2)C=C1C(F)(F)F ISHGNBGFTLNSCV-UHFFFAOYSA-N 0.000 claims description 2
- GSDDFQPXMDVYOD-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-5-yl)-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2C=C3N=CSC3=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 GSDDFQPXMDVYOD-UHFFFAOYSA-N 0.000 claims description 2
- BQNIEYQHHPDLJI-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-6-yl)-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2C=C3SC=NC3=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 BQNIEYQHHPDLJI-UHFFFAOYSA-N 0.000 claims description 2
- DMXWAOUYXWLNOD-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]-3-(trifluoromethyl)phenyl]-4-methyl-3-phthalazin-6-ylbenzamide Chemical compound C1=C(C(F)(F)F)C(CN(C)C)=CC=C1NC(=O)C1=CC=C(C)C(C=2C=C3C=NN=CC3=CC=2)=C1 DMXWAOUYXWLNOD-UHFFFAOYSA-N 0.000 claims description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- XHEISHRKUMLZES-UHFFFAOYSA-N 3-isoquinolin-7-yl-4-methyl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(C=2C=C3C=NC=CC3=CC=2)C(C)=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 XHEISHRKUMLZES-UHFFFAOYSA-N 0.000 claims 1
- HRJNAQDUSGCBOJ-UHFFFAOYSA-N 3-isoquinolin-7-yl-4-methyl-n-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide Chemical compound C1CN(C)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=C(C)C(C=2C=C3C=NC=CC3=CC=2)=C1 HRJNAQDUSGCBOJ-UHFFFAOYSA-N 0.000 claims 1
- SQNGPSFWLCMUMK-UHFFFAOYSA-N 4-[(4-methylpiperazin-1-yl)methyl]-n-(4-methyl-3-quinazolin-6-ylphenyl)-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(C(C)=CC=2)C=2C=C3C=NC=NC3=CC=2)C=C1C(F)(F)F SQNGPSFWLCMUMK-UHFFFAOYSA-N 0.000 claims 1
- OWMQRYCHOXSPEK-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-n-(3-isoquinolin-7-yl-4-methylphenyl)-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(CN(C)C)=CC=C1C(=O)NC1=CC=C(C)C(C=2C=C3C=NC=CC3=CC=2)=C1 OWMQRYCHOXSPEK-UHFFFAOYSA-N 0.000 claims 1
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- KEJIZGVSPJNUSG-UHFFFAOYSA-N 4-methyl-3-phthalazin-6-yl-n-[4-(piperidin-1-ylmethyl)-3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(C=2C=C3C=NN=CC3=CC=2)C(C)=CC=C1C(=O)NC(C=C1C(F)(F)F)=CC=C1CN1CCCCC1 KEJIZGVSPJNUSG-UHFFFAOYSA-N 0.000 claims 1
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- CGTADGCBEXYWNE-JUKNQOCSSA-N zotarolimus Chemical compound N1([C@H]2CC[C@@H](C[C@@H](C)[C@H]3OC(=O)[C@@H]4CCCCN4C(=O)C(=O)[C@@]4(O)[C@H](C)CC[C@H](O4)C[C@@H](/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C3)OC)C[C@H]2OC)C=NN=N1 CGTADGCBEXYWNE-JUKNQOCSSA-N 0.000 description 1
- 229950009819 zotarolimus Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0417905.7A GB0417905D0 (en) | 2004-08-11 | 2004-08-11 | Organic compounds |
| GB0417905.7 | 2004-08-11 | ||
| PCT/EP2005/008695 WO2006015859A1 (en) | 2004-08-11 | 2005-08-10 | Trifluoromethyl substituted benzamides as kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2575316A1 true CA2575316A1 (en) | 2006-02-16 |
Family
ID=33017336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002575316A Abandoned CA2575316A1 (en) | 2004-08-11 | 2005-08-10 | Trifluoromethyl substituted benzamides as kinase inhibitors |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US20080096883A1 (OSRAM) |
| EP (1) | EP1778640A1 (OSRAM) |
| JP (1) | JP2008509187A (OSRAM) |
| KR (1) | KR20070046851A (OSRAM) |
| CN (2) | CN101039914A (OSRAM) |
| AU (1) | AU2005270313A1 (OSRAM) |
| BR (1) | BRPI0514288A (OSRAM) |
| CA (1) | CA2575316A1 (OSRAM) |
| EC (1) | ECSP077235A (OSRAM) |
| GB (1) | GB0417905D0 (OSRAM) |
| IL (1) | IL181169A0 (OSRAM) |
| MA (1) | MA28822B1 (OSRAM) |
| MX (1) | MX2007001642A (OSRAM) |
| NO (1) | NO20071300L (OSRAM) |
| RU (1) | RU2007108861A (OSRAM) |
| TN (1) | TNSN07048A1 (OSRAM) |
| WO (1) | WO2006015859A1 (OSRAM) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070054916A1 (en) † | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
| US7759337B2 (en) | 2005-03-03 | 2010-07-20 | Amgen Inc. | Phthalazine compounds and methods of use |
| JP5079500B2 (ja) * | 2005-04-28 | 2012-11-21 | 協和発酵キリン株式会社 | ２−アミノキナゾリン誘導体 |
| AU2007234382B2 (en) * | 2006-04-05 | 2011-06-09 | Novartis Ag | Combinations comprising BCR-ABL/C-KIT/PDGF-R TK inhibitors for treating cancer |
| BRPI0714307A2 (pt) * | 2006-07-13 | 2014-06-10 | Novartis Ag | Uso de benzamidas trifluormetil-substituídas no tratamento de distúrbios neurológicos |
| WO2008009078A2 (en) | 2006-07-20 | 2008-01-24 | Gilead Sciences, Inc. | 4,6-dl- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections |
| WO2008009077A2 (en) * | 2006-07-20 | 2008-01-24 | Gilead Sciences, Inc. | 4,6-dl- and 2,4,6-trisubstituted quinazoline derivatives and pharmaceutical compositions useful for treating viral infections |
| ATE501124T1 (de) * | 2006-09-05 | 2011-03-15 | Amgen Inc | Phthalazin-, aza- und diazaphthalazinverbindungen und anwendungsverfahren |
| EP2117544A4 (en) * | 2006-12-19 | 2010-03-03 | Univ Texas | BIOMARKER FOR IDENTIFYING REACTIVATION FROM STAT3 TO SRC INHIBITION |
| EP2121692B1 (en) * | 2006-12-22 | 2013-04-10 | Incyte Corporation | Substituted heterocycles as janus kinase inhibitors |
| US8022085B2 (en) | 2007-05-07 | 2011-09-20 | Amgen Inc. | Pyrazolo-pyridinone and pyrazolo-pyrazinone compounds as P38 modulators and methods of use thereof |
| CA2685674C (en) * | 2007-05-07 | 2012-07-17 | Amgen Inc. | Pyrazolo-pyridinone compounds, process for their preparation, and their pharmaceutical use |
| US20100292292A1 (en) * | 2007-09-13 | 2010-11-18 | Link Medicine Corporation | Treatment of Neurodegenerative Diseases Using Indatraline Analogs |
| WO2009117156A1 (en) * | 2008-03-21 | 2009-09-24 | Amgen Inc. | Pyrazolo-pyrazinone compounds and methods of use thereof |
| EP2269993B1 (en) | 2008-04-23 | 2013-02-27 | Kyowa Hakko Kirin Co., Ltd. | 2-aminoquinazoline derivative |
| US8420649B2 (en) | 2008-08-29 | 2013-04-16 | Amgen Inc. | Pyrido[3,2-d]pyridazine-2(1H)-one compounds as p38 modulators and methods of use thereof |
| WO2010025201A1 (en) | 2008-08-29 | 2010-03-04 | Amgen Inc. | Pyridazino- pyridinone compounds for the treatment of protein kinase mediated diseases. |
| US8772481B2 (en) | 2008-10-10 | 2014-07-08 | Amgen Inc. | Aza- and diaza-phthalazine compounds as P38 map kinase modulators and methods of use thereof |
| WO2010042649A2 (en) | 2008-10-10 | 2010-04-15 | Amgen Inc. | PHTHALAZINE COMPOUNDS AS p38 MAP KINASE MODULATORS AND METHODS OF USE THEREOF |
| WO2010096395A1 (en) * | 2009-02-18 | 2010-08-26 | Syntech Solution Llc | Amides as kinase inhibitors |
| JP2012529517A (ja) | 2009-06-09 | 2012-11-22 | アブラクシス バイオサイエンス リミテッド ライアビリティー カンパニー | ベンジル置換トリアジン誘導体類及びそれらの治療応用 |
| KR101457027B1 (ko) | 2009-06-09 | 2014-10-31 | 캘리포니아 캐피탈 에쿼티, 엘엘씨 | 트리아진 유도체와 이들의 치료적 용도 |
| CA2765053C (en) | 2009-06-09 | 2015-08-18 | California Capital Equity, Llc | Isoquinoline, quinoline, and quinazoline derivatives as inhibitors of hedgehog signaling |
| JP2013509444A (ja) * | 2009-10-30 | 2013-03-14 | アリアド・ファーマシューティカルズ・インコーポレイテッド | がんの治療方法及び治療用組成物 |
| CN102675289B (zh) * | 2011-03-18 | 2014-11-05 | 浙江大德药业集团有限公司 | 作为蛋白激酶抑制剂的n-苯基苯甲酰胺衍生物 |
| WO2012148792A1 (en) * | 2011-04-26 | 2012-11-01 | Merck Sharp & Dohme Corp. | Heterocyclic compounds as b-raf inhibitors for treatment of cancer |
| PL3321265T3 (pl) | 2015-03-04 | 2020-11-16 | Gilead Sciences, Inc. | Związki 4,6-diamino-pirydo[3,2-d]pirymidynowe i ich wykorzystanie jako modulatorów receptorów toll-podobnych |
| EP3507288B1 (en) | 2016-09-02 | 2020-08-26 | Gilead Sciences, Inc. | 4,6-diamino-pyrido[3,2-d]pyrimidine derivaties as toll like receptor modulators |
| CA3035346A1 (en) | 2016-09-02 | 2018-03-08 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| TW202210480A (zh) | 2019-04-17 | 2022-03-16 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TW202212339A (zh) | 2019-04-17 | 2022-04-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TWI879779B (zh) | 2019-06-28 | 2025-04-11 | 美商基利科學股份有限公司 | 類鐸受體調節劑化合物的製備方法 |
| CN111904960A (zh) * | 2020-05-19 | 2020-11-10 | 合肥合源药业有限公司 | 一种固体分散体及药用组合物 |
| KR102463217B1 (ko) * | 2020-07-13 | 2022-11-07 | 한국과학기술연구원 | 단백질 키나아제 저해 활성을 갖는 4-아미노퀴나졸린-2-카복스아미드 유도체 및 이를 포함하는 암의 예방, 개선 또는 치료용 약학 조성물 |
| CN111925331A (zh) * | 2020-07-14 | 2020-11-13 | 上海毕得医药科技有限公司 | 一种6-溴酞嗪的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6587829B1 (en) * | 1997-07-31 | 2003-07-01 | Schering Corporation | Method and apparatus for improving patient compliance with prescriptions |
| US6523009B1 (en) * | 1999-11-06 | 2003-02-18 | Bobbi L. Wilkins | Individualized patient electronic medical records system |
| US20030236682A1 (en) * | 1999-11-08 | 2003-12-25 | Heyer Charlette L. | Method and system for managing a healthcare network |
| US6684276B2 (en) * | 2001-03-28 | 2004-01-27 | Thomas M. Walker | Patient encounter electronic medical record system, method, and computer product |
| GB0217757D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
| US20070054916A1 (en) * | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
-
2004
- 2004-08-11 GB GBGB0417905.7A patent/GB0417905D0/en not_active Ceased
-
2005
- 2005-08-10 US US11/573,235 patent/US20080096883A1/en not_active Abandoned
- 2005-08-10 CA CA002575316A patent/CA2575316A1/en not_active Abandoned
- 2005-08-10 CN CNA200580034662XA patent/CN101039914A/zh active Pending
- 2005-08-10 BR BRPI0514288-1A patent/BRPI0514288A/pt not_active IP Right Cessation
- 2005-08-10 RU RU2007108861/04A patent/RU2007108861A/ru not_active Application Discontinuation
- 2005-08-10 EP EP05777531A patent/EP1778640A1/en not_active Withdrawn
- 2005-08-10 WO PCT/EP2005/008695 patent/WO2006015859A1/en not_active Ceased
- 2005-08-10 JP JP2007525252A patent/JP2008509187A/ja active Pending
- 2005-08-10 AU AU2005270313A patent/AU2005270313A1/en not_active Abandoned
- 2005-08-10 CN CN200910175026A patent/CN101696188A/zh active Pending
- 2005-08-10 US US11/201,348 patent/US20060035897A1/en not_active Abandoned
- 2005-08-10 MX MX2007001642A patent/MX2007001642A/es not_active Application Discontinuation
- 2005-08-10 KR KR1020077003238A patent/KR20070046851A/ko not_active Withdrawn
-
2007
- 2007-02-05 IL IL181169A patent/IL181169A0/en unknown
- 2007-02-09 EC EC2007007235A patent/ECSP077235A/es unknown
- 2007-02-09 TN TNP2007000048A patent/TNSN07048A1/en unknown
- 2007-02-22 MA MA29711A patent/MA28822B1/fr unknown
- 2007-03-09 NO NO20071300A patent/NO20071300L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TNSN07048A1 (en) | 2008-06-02 |
| WO2006015859A1 (en) | 2006-02-16 |
| RU2007108861A (ru) | 2008-09-20 |
| CN101039914A (zh) | 2007-09-19 |
| JP2008509187A (ja) | 2008-03-27 |
| US20060035897A1 (en) | 2006-02-16 |
| ECSP077235A (es) | 2007-03-29 |
| MA28822B1 (fr) | 2007-08-01 |
| GB0417905D0 (en) | 2004-09-15 |
| IL181169A0 (en) | 2007-07-04 |
| NO20071300L (no) | 2007-04-19 |
| KR20070046851A (ko) | 2007-05-03 |
| AU2005270313A1 (en) | 2006-02-16 |
| EP1778640A1 (en) | 2007-05-02 |
| MX2007001642A (es) | 2007-04-10 |
| BRPI0514288A (pt) | 2008-06-10 |
| US20080096883A1 (en) | 2008-04-24 |
| CN101696188A (zh) | 2010-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |