AU2009209633C1 - Pyrazine derivatives and their use as protein kinase inhbitors - Google Patents
Pyrazine derivatives and their use as protein kinase inhbitors Download PDFInfo
- Publication number
- AU2009209633C1 AU2009209633C1 AU2009209633A AU2009209633A AU2009209633C1 AU 2009209633 C1 AU2009209633 C1 AU 2009209633C1 AU 2009209633 A AU2009209633 A AU 2009209633A AU 2009209633 A AU2009209633 A AU 2009209633A AU 2009209633 C1 AU2009209633 C1 AU 2009209633C1
- Authority
- AU
- Australia
- Prior art keywords
- indol
- amino
- diamine
- pyrazin
- pyridin
- 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
- 102000001253 Protein Kinase Human genes 0.000 title claims description 8
- 108060006633 protein kinase Proteins 0.000 title claims description 8
- 150000003216 pyrazines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- 238000000034 method Methods 0.000 claims description 64
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 53
- -1 3 -amino-6-pyridin-4-ylpyrazin-2-yl Chemical group 0.000 claims description 50
- 102000004632 fms-Like Tyrosine Kinase 3 Human genes 0.000 claims description 48
- 108010003374 fms-Like Tyrosine Kinase 3 Proteins 0.000 claims description 48
- 208000035475 disorder Diseases 0.000 claims description 44
- 108091000080 Phosphotransferase Proteins 0.000 claims description 24
- 102000020233 phosphotransferase Human genes 0.000 claims description 24
- 208000032839 leukemia Diseases 0.000 claims description 21
- 230000000694 effects Effects 0.000 claims description 20
- 230000002062 proliferating effect Effects 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 19
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 19
- 208000017520 skin disease Diseases 0.000 claims description 19
- 208000014767 Myeloproliferative disease Diseases 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
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- DTLBKXRFWUERQN-UHFFFAOYSA-N 3,5-dibromopyrazin-2-amine Chemical compound NC1=NC=C(Br)N=C1Br DTLBKXRFWUERQN-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 7
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 7
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- JLRIJKVMMZEKDF-UHFFFAOYSA-N 3-n-(1h-indol-5-yl)-5-pyridin-4-ylpyrazine-2,3-diamine Chemical compound N1=C(NC=2C=C3C=CNC3=CC=2)C(N)=NC=C1C1=CC=NC=C1 JLRIJKVMMZEKDF-UHFFFAOYSA-N 0.000 claims description 5
- JQUCLYATBMLCNH-UHFFFAOYSA-N n-(6-pyridin-4-ylpyrazin-2-yl)-1,3-benzothiazol-5-amine Chemical compound C=1C=C2SC=NC2=CC=1NC(N=1)=CN=CC=1C1=CC=NC=C1 JQUCLYATBMLCNH-UHFFFAOYSA-N 0.000 claims description 5
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- KGSLNVDPBRJBIS-UHFFFAOYSA-N 3-n-(1h-indol-5-yl)-5-pyridin-3-ylpyrazine-2,3-diamine Chemical compound N1=C(NC=2C=C3C=CNC3=CC=2)C(N)=NC=C1C1=CC=CN=C1 KGSLNVDPBRJBIS-UHFFFAOYSA-N 0.000 claims description 4
- CDQONHLQZOKYOT-UHFFFAOYSA-N 4-[5-amino-6-(1h-indazol-5-ylamino)pyrazin-2-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN=C(N)C(NC=2C=C3C=NNC3=CC=2)=N1 CDQONHLQZOKYOT-UHFFFAOYSA-N 0.000 claims description 4
- WIGUCJJKVBBMID-UHFFFAOYSA-N 4-[5-amino-6-(1h-indol-4-ylamino)pyrazin-2-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN=C(N)C(NC=2C=3C=CNC=3C=CC=2)=N1 WIGUCJJKVBBMID-UHFFFAOYSA-N 0.000 claims description 4
- AFNQZEVDEAXWPB-UHFFFAOYSA-N 4-[5-amino-6-(1h-indol-5-ylamino)pyrazin-2-yl]-n-(2-cyanoethyl)benzamide Chemical compound N1=C(NC=2C=C3C=CNC3=CC=2)C(N)=NC=C1C1=CC=C(C(=O)NCCC#N)C=C1 AFNQZEVDEAXWPB-UHFFFAOYSA-N 0.000 claims description 4
- XCJXTRXGSPPYKB-UHFFFAOYSA-N 4-[5-amino-6-(1h-indol-5-ylamino)pyrazin-2-yl]-n-(2-methoxyethyl)benzamide Chemical compound C1=CC(C(=O)NCCOC)=CC=C1C1=CN=C(N)C(NC=2C=C3C=CNC3=CC=2)=N1 XCJXTRXGSPPYKB-UHFFFAOYSA-N 0.000 claims description 4
- XLIVSEBIYJLZHS-UHFFFAOYSA-N 5-(2-chloropyridin-4-yl)-3-n-(1h-indol-5-yl)pyrazine-2,3-diamine Chemical compound N1=C(NC=2C=C3C=CNC3=CC=2)C(N)=NC=C1C1=CC=NC(Cl)=C1 XLIVSEBIYJLZHS-UHFFFAOYSA-N 0.000 claims description 4
- FXORCNBUVNOZFA-UHFFFAOYSA-N n-(6-pyridin-4-ylpyrazin-2-yl)-1h-indol-5-amine Chemical compound C=1C=C2NC=CC2=CC=1NC(N=1)=CN=CC=1C1=CC=NC=C1 FXORCNBUVNOZFA-UHFFFAOYSA-N 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- WGFCNCNTGOFBBF-UHFFFAOYSA-N 2-bromopyrazine Chemical compound BrC1=CN=CC=N1 WGFCNCNTGOFBBF-UHFFFAOYSA-N 0.000 claims description 3
- ZULUJEWHWOKCQQ-UHFFFAOYSA-N 3-[5-amino-6-(1h-indol-5-ylamino)pyrazin-2-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=C(NC=3C=C4C=CNC4=CC=3)C(N)=NC=2)=C1 ZULUJEWHWOKCQQ-UHFFFAOYSA-N 0.000 claims description 3
- XRAQYYADKDVFRM-UHFFFAOYSA-N 3-n-(1h-indol-5-yl)-5-thiophen-3-ylpyrazine-2,3-diamine Chemical compound N1=C(NC=2C=C3C=CNC3=CC=2)C(N)=NC=C1C=1C=CSC=1 XRAQYYADKDVFRM-UHFFFAOYSA-N 0.000 claims description 3
- VSVOINYJNQUOIO-UHFFFAOYSA-N 4-[5-amino-6-(1h-indol-5-ylamino)pyrazin-2-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN=C(N)C(NC=2C=C3C=CNC3=CC=2)=N1 VSVOINYJNQUOIO-UHFFFAOYSA-N 0.000 claims description 3
- PJLSSLIIFBCYHB-UHFFFAOYSA-N 4-[6-[(4-hydroxycyclohexyl)amino]pyrazin-2-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN=CC(NC2CCC(O)CC2)=N1 PJLSSLIIFBCYHB-UHFFFAOYSA-N 0.000 claims description 3
- RIKNQTAUPFOPPW-UHFFFAOYSA-N 5-(furan-3-yl)-3-n-(1h-indol-5-yl)pyrazine-2,3-diamine Chemical compound N1=C(NC=2C=C3C=CNC3=CC=2)C(N)=NC=C1C=1C=COC=1 RIKNQTAUPFOPPW-UHFFFAOYSA-N 0.000 claims description 3
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- BZNPATAOUOMBPS-UHFFFAOYSA-N 5-(3-fluorophenyl)-3-n-(1h-indol-5-yl)pyrazine-2,3-diamine Chemical compound N1=C(NC=2C=C3C=CNC3=CC=2)C(N)=NC=C1C1=CC=CC(F)=C1 BZNPATAOUOMBPS-UHFFFAOYSA-N 0.000 claims description 2
- CPYAUFLEMLTQAA-UHFFFAOYSA-N 5-bromopyrazine-2,3-diamine Chemical compound NC1=NC=C(Br)N=C1N CPYAUFLEMLTQAA-UHFFFAOYSA-N 0.000 claims description 2
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- XMUMRVRWCPTVOK-UHFFFAOYSA-N 4-[5-amino-6-[(2-methyl-1h-indol-5-yl)amino]pyrazin-2-yl]benzamide Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C(=NC=1)N)=NC=1C1=CC=C(C(N)=O)C=C1 XMUMRVRWCPTVOK-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
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- 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
- A61K31/4965—Non-condensed pyrazines
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (7)
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| SE0800250-3 | 2008-02-01 | ||
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| US12303908P | 2008-04-04 | 2008-04-04 | |
| US61/123,039 | 2008-04-04 | ||
| SE0801185 | 2008-05-21 | ||
| SE0801185-0 | 2008-05-21 | ||
| PCT/EP2009/050931 WO2009095399A2 (en) | 2008-02-01 | 2009-01-28 | Pyrazine derivatives and their use as protein kinase inhbitors |
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| SI2252597T1 (sl) * | 2008-02-01 | 2014-07-31 | Akinion Pharmaceuticals Ab | Derivati pirazina in njihova uporaba kot inhibitorji protein kinaze |
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| WO2013089636A1 (en) * | 2011-12-15 | 2013-06-20 | Akinion Pharmaceuticals Ab | Processes for manufacturing of a kinase inhibitor |
| AU2013232208B2 (en) * | 2012-03-14 | 2017-04-27 | Indiana University Research And Technology Corporation | Compounds and methods for treating leukemia |
| AU2013250378B2 (en) * | 2012-04-17 | 2016-01-14 | Fujifilm Corporation | Nitrogen-containing heterocyclic compound or salt thereof |
| UY34807A (es) * | 2012-05-16 | 2013-12-31 | Novartis Ag | Derivados monocíclicos de heteroarilcicloalquil- diamina |
| DK3059227T3 (da) | 2013-10-16 | 2019-08-26 | Fujifilm Corp | Salt af en nitrogen-holdig heterocyklisk forbindelse eller krystal deraf, farmaceutisk sammensætning og flt3-hæmmer |
| US10065937B2 (en) | 2014-07-31 | 2018-09-04 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | FLT3 receptor antagonists |
| JP6257782B2 (ja) | 2014-08-22 | 2018-01-10 | 富士フイルム株式会社 | Ｆｌｔ３変異陽性癌を処置するための医薬組成物、変異型ｆｌｔ３阻害剤およびそれらの応用 |
| CN105985322A (zh) * | 2015-03-03 | 2016-10-05 | 苏州翔实医药发展有限公司 | 氨基吡嗪化合物及其用途 |
| JP6412471B2 (ja) | 2015-07-15 | 2018-10-24 | 富士フイルム株式会社 | 含窒素複素環化合物の製造方法およびその中間体 |
| EP3254698A1 (en) | 2016-06-08 | 2017-12-13 | Universite De Montpellier | Flt3 receptor inhibitor at low dosage for the treatment of neuropathic pain |
| WO2018211018A1 (en) | 2017-05-17 | 2018-11-22 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Flt3 inhibitors for improving pain treatments by opioids |
| WO2019018584A1 (en) | 2017-07-18 | 2019-01-24 | GiraFpharma LLC | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
| WO2019057649A1 (en) | 2017-09-19 | 2019-03-28 | INSERM (Institut National de la Santé et de la Recherche Médicale) | METHODS AND PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OF ACUTE MYELOID LEUKEMIA |
| CN110483366B (zh) * | 2018-05-14 | 2022-09-16 | 中国医学科学院药物研究所 | 吲哚类化合物及其制备方法、药物组合物和用途 |
| CN113939291A (zh) | 2019-01-18 | 2022-01-14 | 诺维逊生物股份有限公司 | 1,8-萘啶酮化合物及其用途 |
| WO2020150677A1 (en) * | 2019-01-18 | 2020-07-23 | Nuvation Bio Inc. | Heterocyclic compounds as adenosine antagonists |
| MX2021008650A (es) | 2019-01-18 | 2021-11-03 | Nuvation Bio Inc | Compuestos heterociclicos como antagonistas de adenosina. |
| KR20210142154A (ko) | 2019-03-21 | 2021-11-24 | 옹쎄오 | 암 치료를 위한 키나제 억제제와 조합된 dbait 분자 |
| JP2023500906A (ja) | 2019-11-08 | 2023-01-11 | インサーム（インスティテュ ナシオナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシェ メディカル） | キナーゼ阻害剤に対する獲得抵抗性を有するがんの処置方法 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| CN112574192B (zh) * | 2020-12-24 | 2021-10-01 | 烟台大学 | 氨基酸衍生联噻唑-色胺类抗癌化合物和应用 |
| KR20250075303A (ko) * | 2023-11-21 | 2025-05-28 | (주)신테카바이오 | 크레놀라닙 또는 이의 약학적으로 허용 가능한 염을 포함하는 건선의 예방 또는 치료용 조성물 |
| KR20250075302A (ko) * | 2023-11-21 | 2025-05-28 | (주)신테카바이오 | 크레놀라닙 또는 이의 약학적으로 허용 가능한 염을 포함하는 아토피 피부염의 예방 또는 치료용 조성물 |
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| WO2005058876A1 (en) * | 2003-12-16 | 2005-06-30 | Gpc Biotech Ag | Pyrazine derivatives as effective compounds against infectious diseases |
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| US20040102455A1 (en) * | 2001-01-30 | 2004-05-27 | Burns Christopher John | Method of inhibiting kinases |
| CN100558715C (zh) * | 2002-05-23 | 2009-11-11 | 西托匹亚有限公司 | 蛋白激酶抑制剂 |
| AUPS251502A0 (en) * | 2002-05-23 | 2002-06-13 | Cytopia Pty Ltd | Protein kinase inhibitors |
| GB2400101A (en) | 2003-03-28 | 2004-10-06 | Biofocus Discovery Ltd | Compounds capable of binding to the active site of protein kinases |
| US7563748B2 (en) | 2003-06-23 | 2009-07-21 | Cognis Ip Management Gmbh | Alcohol alkoxylate carriers for pesticide active ingredients |
| JP2007533635A (ja) * | 2003-09-30 | 2007-11-22 | アムジエン・インコーポレーテツド | バニロイド受容体リガンドおよび治療おけるこれらの使用 |
| EP1742935B1 (en) * | 2004-04-13 | 2010-02-24 | Icagen, Inc. | Polycyclic pyrazines as potassium ion channel modulators |
| WO2006000020A1 (en) | 2004-06-29 | 2006-01-05 | European Nickel Plc | Improved leaching of base metals |
| GB0428082D0 (en) * | 2004-12-22 | 2005-01-26 | Welcome Trust The Ltd | Therapeutic compounds |
| TW200801513A (en) | 2006-06-29 | 2008-01-01 | Fermiscan Australia Pty Ltd | Improved process |
| ATE517868T1 (de) * | 2006-08-16 | 2011-08-15 | Boehringer Ingelheim Int | Pyrazinverbindungen, ihre verwendung und herstellungsverfahren |
| WO2008058341A1 (en) * | 2006-11-15 | 2008-05-22 | Cytopia Research Pty Ltd | Inhibitors of kinase activity |
| SI2252597T1 (sl) * | 2008-02-01 | 2014-07-31 | Akinion Pharmaceuticals Ab | Derivati pirazina in njihova uporaba kot inhibitorji protein kinaze |
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- 2009-01-28 WO PCT/EP2009/050931 patent/WO2009095399A2/en not_active Ceased
- 2009-01-28 HR HRP20140547AT patent/HRP20140547T1/hr unknown
- 2009-01-28 AU AU2009209633A patent/AU2009209633C1/en not_active Ceased
- 2009-01-28 KR KR1020107017417A patent/KR101599082B1/ko not_active Expired - Fee Related
- 2009-01-28 JP JP2010544683A patent/JP5562256B2/ja not_active Expired - Fee Related
- 2009-01-28 CA CA2713553A patent/CA2713553A1/en not_active Abandoned
- 2009-01-28 US US12/865,359 patent/US8436171B2/en not_active Expired - Fee Related
- 2009-01-28 BR BRPI0907453-8A patent/BRPI0907453A2/pt not_active Application Discontinuation
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2013
- 2013-03-15 US US13/833,231 patent/US20130203774A1/en not_active Abandoned
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2014
- 2014-04-04 JP JP2014077470A patent/JP2014148522A/ja active Pending
- 2014-06-17 CY CY20141100435T patent/CY1115400T1/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005058876A1 (en) * | 2003-12-16 | 2005-06-30 | Gpc Biotech Ag | Pyrazine derivatives as effective compounds against infectious diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009095399A3 (en) | 2009-10-01 |
| BRPI0907453A2 (pt) | 2015-07-14 |
| EP2252597B1 (en) | 2014-03-19 |
| AU2009209633B2 (en) | 2013-07-18 |
| JP2011510948A (ja) | 2011-04-07 |
| HRP20140547T1 (hr) | 2014-07-18 |
| MX2010007973A (es) | 2010-11-09 |
| EP2671876A2 (en) | 2013-12-11 |
| KR101599082B1 (ko) | 2016-03-02 |
| ES2459297T3 (es) | 2014-05-08 |
| JP2014148522A (ja) | 2014-08-21 |
| HK1149268A1 (en) | 2011-09-30 |
| RU2010136653A (ru) | 2012-03-10 |
| KR20100116599A (ko) | 2010-11-01 |
| DK2252597T3 (da) | 2014-04-28 |
| EP2252597A2 (en) | 2010-11-24 |
| RU2493152C2 (ru) | 2013-09-20 |
| AU2009209633A1 (en) | 2009-08-06 |
| CA2713553A1 (en) | 2009-08-06 |
| WO2009095399A2 (en) | 2009-08-06 |
| CY1115400T1 (el) | 2017-01-04 |
| PT2252597E (pt) | 2014-04-30 |
| US20110098310A1 (en) | 2011-04-28 |
| EP2671876A3 (en) | 2014-02-05 |
| SI2252597T1 (sl) | 2014-07-31 |
| US8436171B2 (en) | 2013-05-07 |
| US20130203774A1 (en) | 2013-08-08 |
| CN101970418A (zh) | 2011-02-09 |
| CN101970418B (zh) | 2013-07-03 |
| JP5562256B2 (ja) | 2014-07-30 |
| PL2252597T3 (pl) | 2014-09-30 |
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