AU2009330503B2 - Amino pyrazole compound - Google Patents
Amino pyrazole compound Download PDFInfo
- Publication number
- AU2009330503B2 AU2009330503B2 AU2009330503A AU2009330503A AU2009330503B2 AU 2009330503 B2 AU2009330503 B2 AU 2009330503B2 AU 2009330503 A AU2009330503 A AU 2009330503A AU 2009330503 A AU2009330503 A AU 2009330503A AU 2009330503 B2 AU2009330503 B2 AU 2009330503B2
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- chloro
- pyridazin
- imidazo
- morpholinomethyl
- 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.)
- Ceased
Links
- -1 Amino pyrazole compound Chemical class 0.000 title claims description 10
- 208000032839 leukemia Diseases 0.000 claims abstract description 9
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims abstract description 8
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 6
- 208000034578 Multiple myelomas Diseases 0.000 claims abstract description 6
- 206010035226 Plasma cell myeloma Diseases 0.000 claims abstract description 6
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 6
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 6
- 208000005017 glioblastoma Diseases 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 22
- SQSZANZGUXWJEA-UHFFFAOYSA-N Gandotinib Chemical compound N1C(C)=CC(NC2=NN3C(CC=4C(=CC(Cl)=CC=4)F)=C(C)N=C3C(CN3CCOCC3)=C2)=N1 SQSZANZGUXWJEA-UHFFFAOYSA-N 0.000 claims description 19
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 208000017733 acquired polycythemia vera Diseases 0.000 claims description 10
- 208000037244 polycythemia vera Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 208000003476 primary myelofibrosis Diseases 0.000 claims description 7
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 208000037398 BCR-ABL1 negative atypical chronic myeloid leukemia Diseases 0.000 claims description 5
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 5
- 208000037379 Myeloid Chronic Atypical BCR-ABL Negative Leukemia Diseases 0.000 claims description 5
- 208000014767 Myeloproliferative disease Diseases 0.000 claims description 5
- 201000004892 atypical chronic myeloid leukemia Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 4
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 4
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- DCLWNTIANRACSB-UHFFFAOYSA-N imidazo[1,2-b]pyridazin-6-amine Chemical compound N1=C(N)C=CC2=NC=CN21 DCLWNTIANRACSB-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
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- 208000016595 therapy related acute myeloid leukemia and myelodysplastic syndrome Diseases 0.000 claims description 4
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- 239000003937 drug carrier Substances 0.000 claims description 3
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 2
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- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 abstract description 3
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- 210000004027 cell Anatomy 0.000 description 98
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 229940105423 erythropoietin Drugs 0.000 description 6
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 6
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- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 6
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- GIMRDGMAHSBGHG-UHFFFAOYSA-N (4-chloro-2-fluorophenyl)-(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanone Chemical compound CC=1N=C2C=CC(Cl)=NN2C=1C(=O)C1=CC=C(Cl)C=C1F GIMRDGMAHSBGHG-UHFFFAOYSA-N 0.000 description 4
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- NHXNBGBJOOYSEA-UHFFFAOYSA-N n'-(6-chloropyridazin-3-yl)-n,n-dimethylethanimidamide Chemical compound CN(C)C(C)=NC1=CC=C(Cl)N=N1 NHXNBGBJOOYSEA-UHFFFAOYSA-N 0.000 description 4
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- XXKYRXQRSRDCAR-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-5-methylpyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1CN1C(C)=CC(N)=N1 XXKYRXQRSRDCAR-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12285408P | 2008-12-16 | 2008-12-16 | |
| US61/122,854 | 2008-12-16 | ||
| PCT/US2009/067056 WO2010074947A1 (en) | 2008-12-16 | 2009-12-08 | Amino pyrazole compound |
Publications (2)
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|---|---|
| AU2009330503A1 AU2009330503A1 (en) | 2010-07-01 |
| AU2009330503B2 true AU2009330503B2 (en) | 2012-06-07 |
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| AU2009330503A Ceased AU2009330503B2 (en) | 2008-12-16 | 2009-12-08 | Amino pyrazole compound |
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| GB2435646A (en) * | 2006-03-01 | 2007-09-05 | Spin Tec Engineering Gmbh | Apparatus and method of extraction of an arthropod gland |
| US8105633B2 (en) * | 2006-03-01 | 2012-01-31 | Spintec Engineering Gmbh | Method and apparatus for extraction of arthropod gland |
| US20110121485A1 (en) * | 2006-10-30 | 2011-05-26 | Spintec Engineering Gmbh | Method and apparatus for the manufacture of a fiber |
| CN103458970A (zh) * | 2011-03-07 | 2013-12-18 | 泰莱托恩基金会 | Tfeb磷酸化抑制剂及其应用 |
| EP2721035B1 (en) * | 2011-06-15 | 2018-06-13 | Life & Brain GmbH | Glioblastoma inhibiting compounds and their use |
| MX367055B (es) | 2012-06-26 | 2019-08-02 | Del Mar Pharmaceuticals | El uso de una composición que comprende dianhidrogalactitol, diacetildianhidrogalactitol, y dibromodulcitol, y análogos o derivados de cada uno para el tratamiento de malignidades resistentes a inhibidores de tirosina cinasa. |
| PL400213A1 (pl) | 2012-08-01 | 2014-02-03 | Celon Pharma Spólka Z Ograniczona Odpowiedzialnoscia | Pochodne imidazo[1,2-b]pirydazyno-6-aminy jako inhibitory kinazy JAK-2 |
| TW201618773A (zh) | 2014-08-11 | 2016-06-01 | 艾森塔製藥公司 | Ｂｔｋ抑制劑、ｐｉ３ｋ抑制劑、ｊａｋ－２抑制劑、及／或ｃｄｋ４／６抑制劑的治療組合物 |
| PT3179991T (pt) | 2014-08-11 | 2021-11-26 | Acerta Pharma Bv | Combinações terapêuticas de um inibidor de btk e um inibidor de bcl-2 |
| HRP20220738T1 (hr) | 2014-08-11 | 2022-08-19 | Acerta Pharma B.V. | Terapijske kombinacije inhibitora btk, inhibitora pd-1 i/ili inhibitora pd-l1 |
| ES2849974T3 (es) * | 2016-11-17 | 2021-08-24 | Bristol Myers Squibb Co | Moduladores de imidazopiridazina de IL-12, IL-23 y/o IFNalfa |
| WO2018167283A1 (en) | 2017-03-17 | 2018-09-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the diagnosis and treatment of pancreatic ductal adenocarcinoma associated neural remodeling |
| US20200088732A1 (en) | 2017-04-13 | 2020-03-19 | INSERM (Institut National de la Santé et de la Recherche Mèdicale) | Methods for the diagnosis and treatment of pancreatic ductal adenocarcinoma |
| KR102328682B1 (ko) | 2018-08-27 | 2021-11-18 | 주식회사 대웅제약 | 신규한 헤테로사이클릭아민 유도체 및 이를 포함하는 약학 조성물 |
| WO2020092015A1 (en) | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
| CN110305140B (zh) | 2019-07-30 | 2020-08-04 | 上海勋和医药科技有限公司 | 二氢吡咯并嘧啶类选择性jak2抑制剂 |
Citations (2)
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|---|---|---|---|---|
| WO2007009773A1 (en) * | 2005-07-21 | 2007-01-25 | Novartis Ag | Pyrazolo[1.5-a]pyrimidin-7-yl amine derivatives as protein kinase inhibitors |
| WO2007044426A2 (en) * | 2005-10-06 | 2007-04-19 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
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| PT1355905E (pt) | 2000-12-21 | 2007-05-31 | Vertex Pharma | Compostos de pirazole úteis como inibidores de proteínaquinase |
| JP2003137785A (ja) * | 2001-08-23 | 2003-05-14 | Takeda Chem Ind Ltd | Ｊｎｋ活性化阻害剤 |
| CN102153540A (zh) | 2001-12-21 | 2011-08-17 | 阿诺麦德股份有限公司 | 具有强效的与趋化因子受体结合的杂环化合物 |
| US8129403B2 (en) | 2005-02-16 | 2012-03-06 | Astrazeneca Ab | Chemical compounds |
| PL1853602T3 (pl) | 2005-02-16 | 2010-11-30 | Astrazeneca Ab | Związki chemiczne |
| EP1899329B1 (en) * | 2005-07-01 | 2011-10-05 | Irm Llc | Pyrimidine-substituted benzimidazole derivatives as protein kinase inhibitors |
| TW200745123A (en) * | 2005-10-06 | 2007-12-16 | Schering Corp | Pyrazolopyrimidines as protein kinase inhibitors |
| JP5144532B2 (ja) * | 2005-11-30 | 2013-02-13 | バーテックス ファーマシューティカルズ インコーポレイテッド | ｃ−Ｍｅｔ阻害剤及び用法 |
| US7989459B2 (en) * | 2006-02-17 | 2011-08-02 | Pharmacopeia, Llc | Purinones and 1H-imidazopyridinones as PKC-theta inhibitors |
| AU2007292924A1 (en) | 2006-09-07 | 2008-03-13 | Biogen Idec Ma Inc. | IRAK modulators for treating an inflammatory condition, cell proliferative disorder, immune disorder |
| BRPI0718266A2 (pt) * | 2006-10-30 | 2014-01-07 | Novartis Ag | Compostos heterocíclicos como agentes anti-inflamatórios. |
| US20100204246A1 (en) * | 2007-04-18 | 2010-08-12 | Astrazeneca Ab | 5-aminopyrazol-3-yl-3h-imidazo (4,5-b) pyridine derivatives and their use for the treatment of cancer |
| JP2010527999A (ja) | 2007-05-23 | 2010-08-19 | フアーマコペイア・エル・エル・シー | ＰＫＣ−θ阻害剤としてのプリノン類および１Ｈ−イミダゾピリジノン類 |
| WO2009062059A2 (en) | 2007-11-08 | 2009-05-14 | Pharmacopeia, Inc. | Isomeric purinones and 1h-imidazopyridinones as pkc-theta inhibitors |
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- 2009-12-08 US US12/632,879 patent/US7897600B2/en not_active Expired - Fee Related
- 2009-12-08 CA CA2744714A patent/CA2744714C/en not_active Expired - Fee Related
- 2009-12-08 KR KR1020117013705A patent/KR101300458B1/ko not_active Expired - Fee Related
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- 2009-12-08 AU AU2009330503A patent/AU2009330503B2/en not_active Ceased
- 2009-12-08 PT PT97958425T patent/PT2379557E/pt unknown
- 2009-12-08 EA EA201170831A patent/EA019554B1/ru not_active IP Right Cessation
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007009773A1 (en) * | 2005-07-21 | 2007-01-25 | Novartis Ag | Pyrazolo[1.5-a]pyrimidin-7-yl amine derivatives as protein kinase inhibitors |
| WO2007044426A2 (en) * | 2005-10-06 | 2007-04-19 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
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