JP2011510948A5 - - Google Patents
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- Publication number
- JP2011510948A5 JP2011510948A5 JP2010544683A JP2010544683A JP2011510948A5 JP 2011510948 A5 JP2011510948 A5 JP 2011510948A5 JP 2010544683 A JP2010544683 A JP 2010544683A JP 2010544683 A JP2010544683 A JP 2010544683A JP 2011510948 A5 JP2011510948 A5 JP 2011510948A5
- Authority
- JP
- Japan
- Prior art keywords
- indol
- amino
- ylpyrazin
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- DTLBKXRFWUERQN-UHFFFAOYSA-N 3,5-dibromopyrazin-2-amine Chemical compound NC1=NC=C(Br)N=C1Br DTLBKXRFWUERQN-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 4
- 102000004632 fms-Like Tyrosine Kinase 3 Human genes 0.000 claims 4
- 108010003374 fms-Like Tyrosine Kinase 3 Proteins 0.000 claims 4
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000002062 proliferating effect Effects 0.000 claims 3
- 208000017520 skin disease Diseases 0.000 claims 3
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000025324 B-cell acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 2
- 102000001253 Protein Kinase Human genes 0.000 claims 2
- 208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 108060006633 protein kinase Proteins 0.000 claims 2
- WGFCNCNTGOFBBF-UHFFFAOYSA-N 2-bromopyrazine Chemical compound BrC1=CN=CC=N1 WGFCNCNTGOFBBF-UHFFFAOYSA-N 0.000 claims 1
- PXKNDTJIISUHEA-UHFFFAOYSA-N 2-methyl-n-(6-pyridin-4-ylpyrazin-2-yl)-1,3-benzothiazol-5-amine Chemical compound C=1C=C2SC(C)=NC2=CC=1NC(N=1)=CN=CC=1C1=CC=NC=C1 PXKNDTJIISUHEA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GPRUENCPIVLEOL-UHFFFAOYSA-N 3-n-(1h-indazol-5-yl)-5-pyridin-4-ylpyrazine-2,3-diamine Chemical compound N1=C(NC=2C=C3C=NNC3=CC=2)C(N)=NC=C1C1=CC=NC=C1 GPRUENCPIVLEOL-UHFFFAOYSA-N 0.000 claims 1
- BXZFFSAGBSMBPG-UHFFFAOYSA-N 3-n-(1h-indol-4-yl)-5-pyridin-4-ylpyrazine-2,3-diamine Chemical compound N1=C(NC=2C=3C=CNC=3C=CC=2)C(N)=NC=C1C1=CC=NC=C1 BXZFFSAGBSMBPG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- YFJIVLKUYIHPAO-UHFFFAOYSA-N 3-n-(2-methyl-1h-indol-5-yl)-5-pyridin-3-ylpyrazine-2,3-diamine Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C(=NC=1)N)=NC=1C1=CC=CN=C1 YFJIVLKUYIHPAO-UHFFFAOYSA-N 0.000 claims 1
- XIBMNHITIDECSX-UHFFFAOYSA-N 3-n-(2-methyl-1h-indol-5-yl)-5-pyridin-4-ylpyrazine-2,3-diamine Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C(=NC=1)N)=NC=1C1=CC=NC=C1 XIBMNHITIDECSX-UHFFFAOYSA-N 0.000 claims 1
- LXSJBTSHCLGLAN-UHFFFAOYSA-N 4-[5-amino-6-(1h-indazol-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=NNC3=CC=2)=N1 LXSJBTSHCLGLAN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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
- AOSWQVNSSMKVLX-UHFFFAOYSA-N 4-[6-(1h-indol-5-ylamino)pyrazin-2-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN=CC(NC=2C=C3C=CNC3=CC=2)=N1 AOSWQVNSSMKVLX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- CPYAUFLEMLTQAA-UHFFFAOYSA-N 5-bromopyrazine-2,3-diamine Chemical compound NC1=NC=C(Br)N=C1N CPYAUFLEMLTQAA-UHFFFAOYSA-N 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010066476 Haematological malignancy Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- VMOKSPUJCKXUFU-HAQNSBGRSA-N NC1=NC=C(C=2C=CN=CC=2)N=C1N[C@H]1CC[C@H](O)CC1 Chemical compound NC1=NC=C(C=2C=CN=CC=2)N=C1N[C@H]1CC[C@H](O)CC1 VMOKSPUJCKXUFU-HAQNSBGRSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 208000018805 childhood acute lymphoblastic leukemia Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 238000009115 maintenance therapy Methods 0.000 claims 1
- 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 1
- 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 1
- FONMNZDZDKPXAM-UHFFFAOYSA-N n-(6-pyridin-4-ylpyrazin-2-yl)-1h-indol-6-amine Chemical compound C=1C=C2C=CNC2=CC=1NC(N=1)=CN=CC=1C1=CC=NC=C1 FONMNZDZDKPXAM-UHFFFAOYSA-N 0.000 claims 1
- ISXVADLDVXRXMT-UHFFFAOYSA-N n-[6-(2-fluoropyridin-4-yl)pyrazin-2-yl]-1h-indol-5-amine Chemical compound C1=NC(F)=CC(C=2N=C(NC=3C=C4C=CNC4=CC=3)C=NC=2)=C1 ISXVADLDVXRXMT-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 210000000130 stem cell Anatomy 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0800250-3 | 2008-02-01 | ||
| SE0800250 | 2008-02-01 | ||
| US12303908P | 2008-04-04 | 2008-04-04 | |
| US61/123,039 | 2008-04-04 | ||
| SE0801185-0 | 2008-05-21 | ||
| SE0801185 | 2008-05-21 | ||
| PCT/EP2009/050931 WO2009095399A2 (en) | 2008-02-01 | 2009-01-28 | Pyrazine derivatives and their use as protein kinase inhbitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014077470A Division JP2014148522A (ja) | 2008-02-01 | 2014-04-04 | 新規化合物、その使用及び製造 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011510948A JP2011510948A (ja) | 2011-04-07 |
| JP2011510948A5 true JP2011510948A5 (enExample) | 2012-03-15 |
| JP5562256B2 JP5562256B2 (ja) | 2014-07-30 |
Family
ID=40527384
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010544683A Expired - Fee Related JP5562256B2 (ja) | 2008-02-01 | 2009-01-28 | 新規化合物、その使用及び製造 |
| JP2014077470A Pending JP2014148522A (ja) | 2008-02-01 | 2014-04-04 | 新規化合物、その使用及び製造 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014077470A Pending JP2014148522A (ja) | 2008-02-01 | 2014-04-04 | 新規化合物、その使用及び製造 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US8436171B2 (enExample) |
| EP (2) | EP2671876A3 (enExample) |
| JP (2) | JP5562256B2 (enExample) |
| KR (1) | KR101599082B1 (enExample) |
| CN (1) | CN101970418B (enExample) |
| AU (1) | AU2009209633C1 (enExample) |
| BR (1) | BRPI0907453A2 (enExample) |
| CA (1) | CA2713553A1 (enExample) |
| CY (1) | CY1115400T1 (enExample) |
| DK (1) | DK2252597T3 (enExample) |
| ES (1) | ES2459297T3 (enExample) |
| HR (1) | HRP20140547T1 (enExample) |
| MX (1) | MX2010007973A (enExample) |
| PL (1) | PL2252597T3 (enExample) |
| PT (1) | PT2252597E (enExample) |
| RU (1) | RU2493152C2 (enExample) |
| SI (1) | SI2252597T1 (enExample) |
| WO (1) | WO2009095399A2 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101599082B1 (ko) * | 2008-02-01 | 2016-03-02 | 어키니언 파마슈티칼스 아베 | 피라진 유도체 및 단백질 키나아제 억제제로서의 이의 용도 |
| WO2011083124A1 (en) | 2010-01-05 | 2011-07-14 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Flt3 receptor antagonists for the treatment or the prevention of pain disorders |
| 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 |
| LT2840080T (lt) * | 2012-04-17 | 2018-02-12 | Fujifilm Corporation | Heterociklinis junginys, turintis azotą, arba jo druska |
| UY34807A (es) * | 2012-05-16 | 2013-12-31 | Novartis Ag | Derivados monocíclicos de heteroarilcicloalquil- diamina |
| EP3059227B1 (en) | 2013-10-16 | 2019-06-26 | FUJIFILM Corporation | Salt of nitrogen-containing heterocyclic compound or crystal thereof, pharmaceutical composition, and flt3 inhibitor |
| WO2016016370A1 (en) | 2014-07-31 | 2016-02-04 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Flt3 receptor antagonists |
| BR112017003186A2 (pt) | 2014-08-22 | 2017-11-28 | Fujifilm Corp | composição farmacêutica para tratamento de cancer positivo para mutação em flt3, inibidor de flt3 mutante e usos dos mesmos |
| 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 |
| MX2020000690A (es) | 2017-07-18 | 2020-07-29 | Nuvation Bio Inc | Compuestos heterociclicos como antagonistas de adenosina. |
| 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 |
| AU2020207952A1 (en) * | 2019-01-18 | 2021-08-26 | Nuvation Bio Inc. | Heterocyclic compounds as adenosine antagonists |
| CA3126931A1 (en) | 2019-01-18 | 2020-07-23 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| EP3911323A4 (en) | 2019-01-18 | 2022-11-16 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
| KR20210142154A (ko) | 2019-03-21 | 2021-11-24 | 옹쎄오 | 암 치료를 위한 키나제 억제제와 조합된 dbait 분자 |
| CN114761006A (zh) | 2019-11-08 | 2022-07-15 | Inserm(法国国家健康医学研究院) | 对激酶抑制剂产生耐药性的癌症的治疗方法 |
| 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 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW225528B (enExample) * | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| RU2340611C2 (ru) * | 2000-09-15 | 2008-12-10 | Вертекс Фармасьютикалз Инкорпорейтед | Производные пиразола, используемые в качестве ингибиторов протеинкиназы |
| WO2002060492A1 (en) * | 2001-01-30 | 2002-08-08 | Cytopia Pty Ltd | Methods of inhibiting kinases |
| DE60317198T2 (de) | 2002-05-23 | 2008-12-04 | Cytopia Research Pty. Ltd., Richmond | Proteinkinaseinhibitoren |
| 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 |
| US7390907B2 (en) * | 2003-09-30 | 2008-06-24 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| WO2005058876A1 (en) * | 2003-12-16 | 2005-06-30 | Gpc Biotech Ag | Pyrazine derivatives as effective compounds against infectious diseases |
| US7642354B2 (en) * | 2004-04-13 | 2010-01-05 | 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 |
| EP2061762B1 (en) * | 2006-08-16 | 2011-07-27 | Boehringer Ingelheim International GmbH | Pyrazine compounds, their use and methods of preparation |
| EP3048099A3 (en) * | 2006-11-15 | 2016-09-21 | YM BioSciences Australia Pty Ltd | Inhibitors of kinase activity |
| KR101599082B1 (ko) * | 2008-02-01 | 2016-03-02 | 어키니언 파마슈티칼스 아베 | 피라진 유도체 및 단백질 키나아제 억제제로서의 이의 용도 |
-
2009
- 2009-01-28 KR KR1020107017417A patent/KR101599082B1/ko not_active Expired - Fee Related
- 2009-01-28 PL PL09706385T patent/PL2252597T3/pl unknown
- 2009-01-28 RU RU2010136653/04A patent/RU2493152C2/ru not_active IP Right Cessation
- 2009-01-28 HR HRP20140547AT patent/HRP20140547T1/hr unknown
- 2009-01-28 EP EP13182880.8A patent/EP2671876A3/en not_active Withdrawn
- 2009-01-28 JP JP2010544683A patent/JP5562256B2/ja not_active Expired - Fee Related
- 2009-01-28 PT PT97063853T patent/PT2252597E/pt unknown
- 2009-01-28 US US12/865,359 patent/US8436171B2/en not_active Expired - Fee Related
- 2009-01-28 ES ES09706385.3T patent/ES2459297T3/es active Active
- 2009-01-28 AU AU2009209633A patent/AU2009209633C1/en not_active Ceased
- 2009-01-28 BR BRPI0907453-8A patent/BRPI0907453A2/pt not_active Application Discontinuation
- 2009-01-28 MX MX2010007973A patent/MX2010007973A/es active IP Right Grant
- 2009-01-28 CN CN2009801038291A patent/CN101970418B/zh not_active Expired - Fee Related
- 2009-01-28 WO PCT/EP2009/050931 patent/WO2009095399A2/en not_active Ceased
- 2009-01-28 SI SI200930949T patent/SI2252597T1/sl unknown
- 2009-01-28 DK DK09706385.3T patent/DK2252597T3/da active
- 2009-01-28 CA CA2713553A patent/CA2713553A1/en not_active Abandoned
- 2009-01-28 EP EP09706385.3A patent/EP2252597B1/en active Active
-
2013
- 2013-03-15 US US13/833,231 patent/US20130203774A1/en not_active Abandoned
-
2014
- 2014-04-04 JP JP2014077470A patent/JP2014148522A/ja active Pending
- 2014-06-17 CY CY20141100435T patent/CY1115400T1/el unknown
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