CA2796008A1 - Inhibitors of protein tyrosine kinase activity - Google Patents
Inhibitors of protein tyrosine kinase activity Download PDFInfo
- Publication number
- CA2796008A1 CA2796008A1 CA2796008A CA2796008A CA2796008A1 CA 2796008 A1 CA2796008 A1 CA 2796008A1 CA 2796008 A CA2796008 A CA 2796008A CA 2796008 A CA2796008 A CA 2796008A CA 2796008 A1 CA2796008 A1 CA 2796008A1
- Authority
- CA
- Canada
- Prior art keywords
- c6alkyl
- heterocyclyl
- formula
- group
- optionally substituted
- 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
- 230000000694 effects Effects 0.000 title claims abstract description 52
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 title abstract description 38
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 title abstract description 38
- 239000003112 inhibitor Substances 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 708
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 120
- 239000000203 mixture Substances 0.000 claims abstract description 106
- 201000010099 disease Diseases 0.000 claims abstract description 89
- 238000000034 method Methods 0.000 claims abstract description 49
- 230000005764 inhibitory process Effects 0.000 claims abstract description 39
- 230000002062 proliferating effect Effects 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 469
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 241
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 180
- -1 -O-aryl Chemical group 0.000 claims description 151
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 120
- 125000003118 aryl group Chemical group 0.000 claims description 118
- 229910052739 hydrogen Inorganic materials 0.000 claims description 93
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 93
- 125000001072 heteroaryl group Chemical group 0.000 claims description 90
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 86
- 229910052757 nitrogen Inorganic materials 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
- 150000003839 salts Chemical class 0.000 claims description 64
- 229920006395 saturated elastomer Polymers 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 229940002612 prodrug Drugs 0.000 claims description 50
- 239000000651 prodrug Substances 0.000 claims description 50
- 239000012453 solvate Substances 0.000 claims description 47
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 229910052717 sulfur Inorganic materials 0.000 claims description 46
- 150000001204 N-oxides Chemical class 0.000 claims description 41
- 108091000080 Phosphotransferase Proteins 0.000 claims description 39
- 150000004677 hydrates Chemical class 0.000 claims description 39
- 125000002883 imidazolyl group Chemical group 0.000 claims description 39
- 102000020233 phosphotransferase Human genes 0.000 claims description 39
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
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- 230000002401 inhibitory effect Effects 0.000 claims description 25
- 230000033115 angiogenesis Effects 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 12
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
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- 125000004122 cyclic group Chemical group 0.000 claims description 10
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
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- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 5
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- 102200071164 rs104894885 Human genes 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
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- 108010009202 Growth Factor Receptors Proteins 0.000 abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 248
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 138
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 136
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- 229910001868 water Inorganic materials 0.000 description 81
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
- 239000011541 reaction mixture Substances 0.000 description 71
- 238000005481 NMR spectroscopy Methods 0.000 description 64
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- 239000007787 solid Substances 0.000 description 54
- 239000000243 solution Substances 0.000 description 53
- 125000004043 oxo group Chemical group O=* 0.000 description 46
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 43
- 239000007864 aqueous solution Substances 0.000 description 38
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
- 210000004027 cell Anatomy 0.000 description 34
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 32
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- 229910052740 iodine Inorganic materials 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
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- 239000000725 suspension Substances 0.000 description 29
- 125000002837 carbocyclic group Chemical group 0.000 description 25
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- 241001465754 Metazoa Species 0.000 description 24
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- 210000004204 blood vessel Anatomy 0.000 description 22
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- 241000124008 Mammalia Species 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 206010028980 Neoplasm Diseases 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 125000000392 cycloalkenyl group Chemical group 0.000 description 20
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
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- 230000012010 growth Effects 0.000 description 14
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 14
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/005—Enzyme inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32480310P | 2010-04-16 | 2010-04-16 | |
| US61/324,803 | 2010-04-16 | ||
| PCT/CA2011/000394 WO2011127567A1 (en) | 2010-04-16 | 2011-04-08 | Inhibitors of protein tyrosine kinase activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2796008A1 true CA2796008A1 (en) | 2011-10-20 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2796008A Abandoned CA2796008A1 (en) | 2010-04-16 | 2011-04-08 | Inhibitors of protein tyrosine kinase activity |
| CA2796054A Abandoned CA2796054A1 (en) | 2010-04-16 | 2011-04-08 | Inhibitors of protein tyrosine kinase activity and use thereof to treat ophthalmic disorders |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| CA2796054A Abandoned CA2796054A1 (en) | 2010-04-16 | 2011-04-08 | Inhibitors of protein tyrosine kinase activity and use thereof to treat ophthalmic disorders |
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| Country | Link |
|---|---|
| US (3) | US8906852B2 (enExample) |
| EP (2) | EP2563794A4 (enExample) |
| JP (2) | JP2013523846A (enExample) |
| KR (2) | KR20130058006A (enExample) |
| CN (2) | CN102947315A (enExample) |
| AR (2) | AR080871A1 (enExample) |
| AU (2) | AU2011241422B2 (enExample) |
| CA (2) | CA2796008A1 (enExample) |
| CO (2) | CO6640224A2 (enExample) |
| EA (2) | EA201291052A1 (enExample) |
| MX (2) | MX2012012031A (enExample) |
| MY (1) | MY157319A (enExample) |
| NZ (2) | NZ602954A (enExample) |
| PH (2) | PH12012502070A1 (enExample) |
| SG (2) | SG184883A1 (enExample) |
| TW (2) | TW201204735A (enExample) |
| UA (1) | UA108878C2 (enExample) |
| WO (2) | WO2011127567A1 (enExample) |
| ZA (2) | ZA201207482B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2183254B1 (en) * | 2007-08-29 | 2017-06-21 | MethylGene Inc. | Inhibitors of protein tyrosine kinase activity |
| MX2010009729A (es) * | 2008-03-05 | 2010-12-21 | Methylgene Inc | Inhibidores de actividad de proteina tirosina quinasa. |
| MX2012012031A (es) * | 2010-04-16 | 2012-12-17 | Methylgene Inc | Inhibidores de la actividad de la proteina tirosina quinasa y uso de los mismos para tratar transtornos oftalmicos. |
| US20130090327A1 (en) * | 2011-09-30 | 2013-04-11 | Methylgene Inc. | Inhibitors of Protein Tyrosine Kinase Activity |
| WO2013044361A1 (en) * | 2011-09-30 | 2013-04-04 | Methylgene Inc. | Inhibitors of protein tyrosine kinase activity |
| US20130096135A1 (en) * | 2011-09-30 | 2013-04-18 | Methylgene Inc. | Selected Inhibitors of Protein Tyrosine Kinase Activity |
| ES2593533T3 (es) | 2011-12-15 | 2016-12-09 | Pfizer Limited | Derivados de sulfonamida |
| EP3200589B1 (en) | 2014-09-10 | 2026-03-11 | Temple University Of The Commonwealth System Of Higher Education | Novel 5-hydroxytryptamine receptor 7 activity modulators and their method of use |
| US20180221365A1 (en) * | 2015-05-12 | 2018-08-09 | Temple University-Of The Commonwealth System Of Higher Education | Novel sigma-2 receptor binders and their method of use |
| JP6664170B2 (ja) * | 2015-08-31 | 2020-03-13 | 広栄化学工業株式会社 | アミノヒドロキシピリジン化合物の製造方法 |
| CN108530464B (zh) * | 2017-03-02 | 2020-10-27 | 深圳海王医药科技研究院有限公司 | 一种多靶点激酶抑制剂 |
| CN121108077A (zh) * | 2025-09-02 | 2025-12-12 | 领泰生物医药(绍兴)有限公司 | 一种含氮杂环化合物的制备方法及其中间体 |
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| US20050020619A1 (en) * | 2003-07-24 | 2005-01-27 | Patrick Betschmann | Thienopyridine kinase inhibitors |
| EP1781664B1 (en) * | 2004-07-30 | 2013-09-04 | MethylGene Inc. | Inhibitors of vegf receptor and hgf receptor signaling |
| AU2006229343A1 (en) * | 2005-03-28 | 2006-10-05 | Kirin Pharma Kabushiki Kaisha | Thienopyridine derivative, or quinoline derivative, or quinazoline derivative, having c-Met autophosphorylation inhibiting potency |
| JO2787B1 (en) * | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| MX2007014617A (es) * | 2005-05-20 | 2008-02-11 | Methylgene Inc | Inhibidores de senalizacion de receptor de factor de crecimiento endotelial bascular y receptor de factor de crecimiento de hepatocitos. |
| WO2008041053A2 (en) | 2005-05-20 | 2008-04-10 | Methylgene, Inc. | Inhibitors of vegf receptor and hgf receptor signaling |
| EP2183254B1 (en) * | 2007-08-29 | 2017-06-21 | MethylGene Inc. | Inhibitors of protein tyrosine kinase activity |
| WO2009026720A1 (en) * | 2007-08-29 | 2009-03-05 | Methylgene Inc. | Processes and intermediates for preparing fused heterocyclic kinase inhibitors |
| MX2010009729A (es) * | 2008-03-05 | 2010-12-21 | Methylgene Inc | Inhibidores de actividad de proteina tirosina quinasa. |
| MX2012012031A (es) * | 2010-04-16 | 2012-12-17 | Methylgene Inc | Inhibidores de la actividad de la proteina tirosina quinasa y uso de los mismos para tratar transtornos oftalmicos. |
| WO2013044361A1 (en) * | 2011-09-30 | 2013-04-04 | Methylgene Inc. | Inhibitors of protein tyrosine kinase activity |
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- 2011-04-08 TW TW100112308A patent/TW201204735A/zh unknown
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- 2011-04-08 AR ARP110101195A patent/AR080875A1/es unknown
- 2011-04-08 CN CN201180029735.1A patent/CN103025740B/zh not_active Expired - Fee Related
- 2011-04-08 MX MX2012012032A patent/MX2012012032A/es not_active Application Discontinuation
- 2011-04-08 CA CA2796054A patent/CA2796054A1/en not_active Abandoned
-
2012
- 2012-10-05 ZA ZA2012/07482A patent/ZA201207482B/en unknown
- 2012-10-09 ZA ZA2012/07557A patent/ZA201207557B/en unknown
- 2012-11-15 CO CO12207317A patent/CO6640224A2/es active IP Right Grant
- 2012-11-15 CO CO12207310A patent/CO6630193A2/es active IP Right Grant
-
2014
- 2014-06-18 US US14/308,408 patent/US20140315801A1/en not_active Abandoned
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