KR20130058006A - 단백질 티로신 키나아제 활성의 억제제 - Google Patents
단백질 티로신 키나아제 활성의 억제제 Download PDFInfo
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- KR20130058006A KR20130058006A KR1020127030161A KR20127030161A KR20130058006A KR 20130058006 A KR20130058006 A KR 20130058006A KR 1020127030161 A KR1020127030161 A KR 1020127030161A KR 20127030161 A KR20127030161 A KR 20127030161A KR 20130058006 A KR20130058006 A KR 20130058006A
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- Prior art keywords
- alkyl
- heterocyclyl
- substituted
- compound
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- 230000000694 effects Effects 0.000 title claims abstract description 56
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 title abstract description 37
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 title abstract description 37
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- 201000010099 disease Diseases 0.000 claims abstract description 93
- 238000000034 method Methods 0.000 claims abstract description 46
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 466
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 237
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 218
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 175
- 125000003118 aryl group Chemical group 0.000 claims description 137
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 98
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 87
- 229920006395 saturated elastomer Polymers 0.000 claims description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
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- 125000005843 halogen group Chemical group 0.000 claims description 44
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- 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 41
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- 238000011282 treatment Methods 0.000 claims description 20
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 19
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000004885 piperazines Chemical class 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 166
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- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 42
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- 239000007864 aqueous solution Substances 0.000 description 40
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
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- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
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- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- RYRXEENRCNVKPA-UHFFFAOYSA-N tert-butyl n-[[6-(7-chlorothieno[3,2-b]pyridin-2-yl)pyridin-3-yl]methyl]-n-(2-methoxyethyl)carbamate Chemical compound N1=CC(CN(CCOC)C(=O)OC(C)(C)C)=CC=C1C1=CC2=NC=CC(Cl)=C2S1 RYRXEENRCNVKPA-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 description 1
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- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- 230000008733 trauma Effects 0.000 description 1
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- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical group 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
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 |
|---|---|
| KR20130058006A true KR20130058006A (ko) | 2013-06-03 |
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Family Applications (2)
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| KR1020127029841A Withdrawn KR20130100234A (ko) | 2010-04-16 | 2011-04-08 | 단백질 티로신 키나아제 활성의 억제 및 안구 질환을 치료하는 이의 용도 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127029841A Withdrawn KR20130100234A (ko) | 2010-04-16 | 2011-04-08 | 단백질 티로신 키나아제 활성의 억제 및 안구 질환을 치료하는 이의 용도 |
Country Status (19)
| 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 |
|---|---|---|---|---|
| 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 CA CA2796008A patent/CA2796008A1/en not_active Abandoned
- 2011-04-08 TW TW100112308A patent/TW201204735A/zh unknown
- 2011-04-08 SG SG2012076733A patent/SG184883A1/en unknown
- 2011-04-08 WO PCT/CA2011/000394 patent/WO2011127567A1/en not_active Ceased
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- 2011-04-08 TW TW100112307A patent/TW201204734A/zh unknown
- 2011-04-08 KR KR1020127029841A patent/KR20130100234A/ko not_active Withdrawn
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- 2011-04-08 AU AU2011241420A patent/AU2011241420B2/en not_active Ceased
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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
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2012
- 2012-10-05 ZA ZA2012/07482A patent/ZA201207482B/en unknown
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