JP5576370B2 - Chk−1阻害剤としての6置換2−ヘテロシクリルアミノピラジン化合物 - Google Patents
Chk−1阻害剤としての6置換2−ヘテロシクリルアミノピラジン化合物 Download PDFInfo
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- JP5576370B2 JP5576370B2 JP2011521675A JP2011521675A JP5576370B2 JP 5576370 B2 JP5576370 B2 JP 5576370B2 JP 2011521675 A JP2011521675 A JP 2011521675A JP 2011521675 A JP2011521675 A JP 2011521675A JP 5576370 B2 JP5576370 B2 JP 5576370B2
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- 0 C*c(cccc1)c1N Chemical compound C*c(cccc1)c1N 0.000 description 35
- DGNRODPHXNTZGI-UHFFFAOYSA-N C[n]1c([s]cc2)c2nc1 Chemical compound C[n]1c([s]cc2)c2nc1 DGNRODPHXNTZGI-UHFFFAOYSA-N 0.000 description 2
- GKVVKWNIYISLDO-UHFFFAOYSA-N C[n]1c(cncc2)c2nc1 Chemical compound C[n]1c(cncc2)c2nc1 GKVVKWNIYISLDO-UHFFFAOYSA-N 0.000 description 2
- LYVKKZOVJNJVGG-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)CCC1OC)O Chemical compound CC(C)(C)OC(N(CC1)CCC1OC)O LYVKKZOVJNJVGG-UHFFFAOYSA-N 0.000 description 1
- AKQXKEBCONUWCL-MRVPVSSYSA-N CC(C)(C)OC(N(CCC1)C[C@@H]1N)=O Chemical compound CC(C)(C)OC(N(CCC1)C[C@@H]1N)=O AKQXKEBCONUWCL-MRVPVSSYSA-N 0.000 description 1
- WZTRNDPEZWOSCB-MRXNPFEDSA-N CC(C)Oc(cc1)cc2c1nc[n]2C1=CNCC(N[C@H](CC2)CN2C(OC(C)(C)C)=O)=N1 Chemical compound CC(C)Oc(cc1)cc2c1nc[n]2C1=CNCC(N[C@H](CC2)CN2C(OC(C)(C)C)=O)=N1 WZTRNDPEZWOSCB-MRXNPFEDSA-N 0.000 description 1
- YZSQFOZHYILAOE-GFCCVEGCSA-N CC(C)Oc1ccc2nc[n](-c3c[nH]c(N[C@H]4CNCC4)n3)c2c1 Chemical compound CC(C)Oc1ccc2nc[n](-c3c[nH]c(N[C@H]4CNCC4)n3)c2c1 YZSQFOZHYILAOE-GFCCVEGCSA-N 0.000 description 1
- IRMMJNNGUHDJGF-PLNGDYQASA-N CC(C/C=C\C)C1=NNC(C)N1 Chemical compound CC(C/C=C\C)C1=NNC(C)N1 IRMMJNNGUHDJGF-PLNGDYQASA-N 0.000 description 1
- LSXIDQCXWUGDBF-WUJWULDRSA-N CCOc(cc1nc2)ncc1[n]2-c1cncc(NC(CNCC2)[C@H]2OC)n1 Chemical compound CCOc(cc1nc2)ncc1[n]2-c1cncc(NC(CNCC2)[C@H]2OC)n1 LSXIDQCXWUGDBF-WUJWULDRSA-N 0.000 description 1
- RUQQHOSCJSDPOZ-LWKPJOBUSA-N CCOc(nc1)cc2c1N(c1cncc(NC(CN(CC3)C(OC(C)(C)C)=O)[C@H]3OC)n1)[I]=N2 Chemical compound CCOc(nc1)cc2c1N(c1cncc(NC(CN(CC3)C(OC(C)(C)C)=O)[C@H]3OC)n1)[I]=N2 RUQQHOSCJSDPOZ-LWKPJOBUSA-N 0.000 description 1
- ZFVDYJFUSCLASM-UHFFFAOYSA-N CCOc(ncc1c2nc[nH]1)c2Br Chemical compound CCOc(ncc1c2nc[nH]1)c2Br ZFVDYJFUSCLASM-UHFFFAOYSA-N 0.000 description 1
- RXTYQIDTXITRKI-UHFFFAOYSA-N CCOc(ncc1c2nc[n]1-c1cncc(N)n1)c2Br Chemical compound CCOc(ncc1c2nc[n]1-c1cncc(N)n1)c2Br RXTYQIDTXITRKI-UHFFFAOYSA-N 0.000 description 1
- MYOKYIBZEHRGCO-UHFFFAOYSA-N CCc1cnc2[n]1[o]cc2 Chemical compound CCc1cnc2[n]1[o]cc2 MYOKYIBZEHRGCO-UHFFFAOYSA-N 0.000 description 1
- GQKZBCPTCWJTAS-UHFFFAOYSA-N COCc1ccccc1 Chemical compound COCc1ccccc1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 1
- CXGUBYQTVRSTNL-CHWSQXEVSA-N C[O]([C@H](CC1)N2C[C@@H]1N)=C2[O-]Cc1ccccc1 Chemical compound C[O]([C@H](CC1)N2C[C@@H]1N)=C2[O-]Cc1ccccc1 CXGUBYQTVRSTNL-CHWSQXEVSA-N 0.000 description 1
- HTLFQPBPHXVTGO-UHFFFAOYSA-N C[n](cn1)c2c1[o]cc2 Chemical compound C[n](cn1)c2c1[o]cc2 HTLFQPBPHXVTGO-UHFFFAOYSA-N 0.000 description 1
- SBYIRMAGNZBTBV-UHFFFAOYSA-N C[n](cn1)c2c1[s]cc2 Chemical compound C[n](cn1)c2c1[s]cc2 SBYIRMAGNZBTBV-UHFFFAOYSA-N 0.000 description 1
- KRHZROBTVNDYNW-UHFFFAOYSA-N C[n]1c2cccnc2nc1 Chemical compound C[n]1c2cccnc2nc1 KRHZROBTVNDYNW-UHFFFAOYSA-N 0.000 description 1
- WJEWGMQMZKWXFE-UHFFFAOYSA-N C[n]1c2ccncc2nc1 Chemical compound C[n]1c2ccncc2nc1 WJEWGMQMZKWXFE-UHFFFAOYSA-N 0.000 description 1
- ZUXYWPVLFAJAFZ-UHFFFAOYSA-N Cc1cnc2[n]1ccnc2 Chemical compound Cc1cnc2[n]1ccnc2 ZUXYWPVLFAJAFZ-UHFFFAOYSA-N 0.000 description 1
- IEVWCILNJKOWSM-XNWCZRBMSA-N Cc1nc(Cl)cnc1/C=N/O Chemical compound Cc1nc(Cl)cnc1/C=N/O IEVWCILNJKOWSM-XNWCZRBMSA-N 0.000 description 1
- ZSFPJJJRNUZCEV-UHFFFAOYSA-N Cc1ncccc1N Chemical compound Cc1ncccc1N ZSFPJJJRNUZCEV-UHFFFAOYSA-N 0.000 description 1
- QDWHCSSYZCNHCD-SNVBAGLBSA-N Cl[C@H](N=C1)N=C1c1cnc2[n]1cccc2 Chemical compound Cl[C@H](N=C1)N=C1c1cnc2[n]1cccc2 QDWHCSSYZCNHCD-SNVBAGLBSA-N 0.000 description 1
- LSEAAPGIZCDEEH-UHFFFAOYSA-N Clc1cncc(Cl)n1 Chemical compound Clc1cncc(Cl)n1 LSEAAPGIZCDEEH-UHFFFAOYSA-N 0.000 description 1
- DGLZASSUQVVPDM-UHFFFAOYSA-N Nc(nc1)c(C2N(C=CC=C3)C3=NC2)nc1NCC1CNCCC1 Chemical compound Nc(nc1)c(C2N(C=CC=C3)C3=NC2)nc1NCC1CNCCC1 DGLZASSUQVVPDM-UHFFFAOYSA-N 0.000 description 1
- MFMMFTVFMSLGAM-UHFFFAOYSA-N O=Cc(ncc(Cl)n1)c1Cl Chemical compound O=Cc(ncc(Cl)n1)c1Cl MFMMFTVFMSLGAM-UHFFFAOYSA-N 0.000 description 1
- TYLGVQVJCVFREB-UHFFFAOYSA-N c1c2nccnc2cnc1 Chemical compound c1c2nccnc2cnc1 TYLGVQVJCVFREB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8673208P | 2008-08-06 | 2008-08-06 | |
| US61/086,732 | 2008-08-06 | ||
| US22942809P | 2009-07-29 | 2009-07-29 | |
| US61/229,428 | 2009-07-29 | ||
| PCT/IB2009/053389 WO2010016005A1 (en) | 2008-08-06 | 2009-08-04 | 6 substituted 2-heterocyclylamino pyrazine compounds as chk-1 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011530500A JP2011530500A (ja) | 2011-12-22 |
| JP2011530500A5 JP2011530500A5 (OSRAM) | 2012-09-13 |
| JP5576370B2 true JP5576370B2 (ja) | 2014-08-20 |
Family
ID=41171261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011521675A Expired - Fee Related JP5576370B2 (ja) | 2008-08-06 | 2009-08-04 | Chk−1阻害剤としての6置換2−ヘテロシクリルアミノピラジン化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8518952B2 (OSRAM) |
| EP (1) | EP2328890B1 (OSRAM) |
| JP (1) | JP5576370B2 (OSRAM) |
| AT (1) | ATE542813T1 (OSRAM) |
| CA (1) | CA2731368C (OSRAM) |
| ES (1) | ES2378513T3 (OSRAM) |
| WO (1) | WO2010016005A1 (OSRAM) |
Families Citing this family (53)
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| EP2376485B1 (en) | 2008-12-19 | 2017-12-06 | Vertex Pharmaceuticals Incorporated | Pyrazine derivatives useful as inhibitors of atr kinase |
| AU2010226490A1 (en) * | 2009-03-20 | 2011-10-06 | Amgen Inc. | Inhibitors of PI3 kinase |
| NZ599597A (en) | 2009-10-30 | 2013-05-31 | Janssen Pharmaceutica Nv | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| EP2338888A1 (en) * | 2009-12-24 | 2011-06-29 | Almirall, S.A. | Imidazopyridine derivatives as JAK inhibitors |
| EP2360158A1 (en) * | 2010-02-18 | 2011-08-24 | Almirall, S.A. | Pyrazole derivatives as jak inhibitors |
| UY33213A (es) * | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| JP2013526540A (ja) * | 2010-05-12 | 2013-06-24 | 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 | Atrキナーゼ阻害剤として有用な化合物 |
| KR20130066633A (ko) | 2010-05-12 | 2013-06-20 | 버텍스 파마슈티칼스 인코포레이티드 | Atr 키나제의 억제제로서 유용한 화합물 |
| EP2463289A1 (en) | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors |
| WO2013000924A1 (en) | 2011-06-27 | 2013-01-03 | Janssen Pharmaceutica Nv | 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES |
| EP2554544A1 (en) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Pyridin-2(1h)-one derivatives as jak inhibitors |
| KR102056586B1 (ko) | 2011-09-30 | 2019-12-18 | 버텍스 파마슈티칼스 인코포레이티드 | Atr 억제제를 이용한 췌장암 및 비소세포 폐암의 치료 |
| BR112014007721B1 (pt) | 2011-09-30 | 2022-11-01 | Vertex Pharmaceuticals Incorporated | Processos para preparar compostos úteis como inibidores de atr quinase |
| WO2013066729A1 (en) | 2011-10-31 | 2013-05-10 | Merck Sharp & Dohme Corp. | Aminopyrimidinones as interleukin receptor-associated kinase inhibitors |
| JP2015515478A (ja) | 2012-04-05 | 2015-05-28 | 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Vertex Pharmaceuticals Incorporated | Atrキナーゼの阻害剤として有用な化合物及びそれらの併用療法 |
| WO2014001314A1 (en) | 2012-06-26 | 2014-01-03 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| AU2013289284B2 (en) | 2012-07-09 | 2017-03-30 | Janssen Pharmaceutica Nv | Inhibitors of phosphodiesterase 10 enzyme |
| US8999632B2 (en) | 2012-10-04 | 2015-04-07 | Vertex Pharmaceuticals Incorporated | Method for measuring ATR inhibition mediated increases in DNA damage |
| EP2922828B1 (en) | 2012-11-21 | 2020-07-08 | PTC Therapeutics, Inc. | 4,6-diamino-pyrimidine derivatives as bmi-1 inhibitors for treating cancer |
| CN103254121B (zh) * | 2013-04-08 | 2015-08-26 | 洛阳师范学院 | 一种合成(3r,4r)-n-pg-4-甲基-3-甲胺基哌啶的方法 |
| WO2015076800A1 (en) | 2013-11-21 | 2015-05-28 | Ptc Therapeutics, Inc. | Substituted pyridine and pyrazine bmi-1 inhibitors |
| MD4649C1 (ro) | 2013-12-05 | 2020-04-30 | Pfizer Inc. | Pirol[2,3-d]pirimidinil, pirol[2,3-b]pirazinil şi pirol[2,3-d]piridinil acrilamide |
| US9145393B2 (en) * | 2014-01-24 | 2015-09-29 | Confluence Life Sciences, Inc. | Arylpyridinone ITK inhibitors for treating inflammation and cancer |
| CA2948173C (en) | 2014-05-09 | 2018-06-19 | Pimera, Inc. | Quinoline compounds and uses thereof |
| US9758518B2 (en) | 2015-03-04 | 2017-09-12 | Pimera, Inc. | Compositions, uses and methods for making them |
| US9695200B2 (en) | 2015-01-23 | 2017-07-04 | Confluence Life Sciences, Inc. | Heterocyclic ITK inhibitors for treating inflammation and cancer |
| WO2016178110A1 (en) | 2015-05-01 | 2016-11-10 | Pfizer Inc. | Pyrrolo[2,3-d]pyrimidinyl, pyrrolo[2,3-b]pyrazinyl, pyrrolo[2,3-b]pyridinyl acrylamides and epoxides thereof |
| CN105130991B (zh) * | 2015-07-10 | 2017-09-19 | 成都知普莱生物医药科技有限公司 | 一种合成骨形态发生蛋白受体抑制剂的方法 |
| KR102678021B1 (ko) | 2015-09-30 | 2024-06-26 | 버텍스 파마슈티칼스 인코포레이티드 | Dna 손상제와 병용되는, atr 저해제를 포함하는 암 치료용 약제학적 조성물 |
| EP3712153B1 (en) | 2016-02-24 | 2021-12-01 | Pfizer Inc. | Pyrazolo[1,5-a]pyrazin-4-yl derivatives as jak-inhibitors |
| WO2018140648A1 (en) | 2017-01-25 | 2018-08-02 | Eric Jon Jacobsen | Pyrrolopyrimidine itk inhibitors for treating inflammation and cancer |
| CN110709400A (zh) | 2017-03-28 | 2020-01-17 | 皮梅拉股份有限公司 | Pol1抑制剂的新型晶体形式 |
| CN107056681B (zh) * | 2017-03-30 | 2019-10-01 | 广州白云山光华制药股份有限公司 | 一种托法替布中间体的制备方法 |
| US11254668B2 (en) | 2017-08-14 | 2022-02-22 | Pfizer Inc. | Pyrazolo[1,5-A]pyrazin-4-yl and related derivatives |
| CN107474047B (zh) * | 2017-08-29 | 2019-10-29 | 浙江工业大学 | 1,2,4-三唑并杂环类化合物的合成方法 |
| CN107827811B (zh) * | 2017-11-15 | 2021-01-29 | 上海皓伯化工科技有限公司 | 一种制备n-取代-1,2,3,6-四氢吡啶的方法 |
| JP2021151955A (ja) * | 2018-05-22 | 2021-09-30 | 株式会社カネカ | 光学活性−cis−アミノピペリジンの製造方法 |
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| UY38705A (es) | 2019-05-23 | 2020-12-31 | Irbm S P A | Inhibidores tricíclicos sustituidos con oxalamido del virus de hepatitis b |
| CA3186583A1 (en) * | 2020-06-11 | 2021-12-16 | Chdi Foundation, Inc. | Heterocyclic compounds and imaging agents for imaging huntingtin protein |
| WO2022026935A1 (en) * | 2020-07-31 | 2022-02-03 | Children's Hospital Medical Center | Multi-cyclic irak and flt3 inhibiting compounds and uses thereof |
| KR102473645B1 (ko) * | 2020-08-28 | 2022-12-05 | (주)부흥산업사 | (2S,5R)-벤질 5-(t-부톡시카르보닐아미노)-2-메틸피페리딘-1-카르복실레이트의 제조방법 |
| CA3226908A1 (en) * | 2021-07-30 | 2023-02-02 | Scott Bryan HOYT | Multi-cyclic irak and flt3 inhibiting compounds and uses thereof |
| CA3258667A1 (en) * | 2022-06-10 | 2023-12-14 | Interline Therapeutics Inc. | IMIDAZO(1,2-A)PYRIDINE DERIVATIVES USED AS RIPK2 INHIBITORS |
| AR129535A1 (es) | 2022-06-21 | 2024-09-04 | Syngenta Crop Protection Ag | Derivados de carboxamida heterocíclicos bicíclicos microbiocidas |
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| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| GB9518953D0 (en) * | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| WO2000035298A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Chewing gum containing medicament active agents |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| GB9722320D0 (en) * | 1997-10-22 | 1997-12-17 | Janssen Pharmaceutica Nv | Human cell cycle checkpoint proteins |
| US6383744B1 (en) * | 1998-07-10 | 2002-05-07 | Incyte Genomics, Inc. | Human checkpoint kinase |
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| CA2385257A1 (en) | 1999-09-22 | 2001-03-29 | Canbas Co., Ltd. | Compositions and methods for inhibiting g2 cell cycle arrest and sensitizing cells to dna damaging agents |
| US6211164B1 (en) * | 2000-03-10 | 2001-04-03 | Abbott Laboratories | Antisense oligonucleotides of the human chk1 gene and uses thereof |
| UY27087A1 (es) | 2001-01-05 | 2002-06-20 | Pfizer | Anticuerpos contra el receptor del factor de crecimiento similar a insulina |
| UA76977C2 (en) | 2001-03-02 | 2006-10-16 | Icos Corp | Aryl- and heteroaryl substituted chk1 inhibitors and their use as radiosensitizers and chemosensitizers |
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| US20080070930A1 (en) * | 2006-08-24 | 2008-03-20 | Huang Kenneth H | Pyrimidine and Pyrazine Derivatives |
| US8183245B2 (en) | 2007-10-25 | 2012-05-22 | Merck Sharp & Dohme Corp. | Pyrazine substituted pyrrolopyridines as inhibitors of JAK and PDK1 |
-
2009
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- 2009-08-04 CA CA2731368A patent/CA2731368C/en not_active Expired - Fee Related
- 2009-08-04 WO PCT/IB2009/053389 patent/WO2010016005A1/en not_active Ceased
- 2009-08-04 US US13/057,558 patent/US8518952B2/en not_active Expired - Fee Related
- 2009-08-04 EP EP09786799A patent/EP2328890B1/en not_active Not-in-force
- 2009-08-04 ES ES09786799T patent/ES2378513T3/es active Active
- 2009-08-04 JP JP2011521675A patent/JP5576370B2/ja not_active Expired - Fee Related
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|---|---|
| US20110144084A1 (en) | 2011-06-16 |
| WO2010016005A1 (en) | 2010-02-11 |
| ES2378513T3 (es) | 2012-04-13 |
| US8518952B2 (en) | 2013-08-27 |
| CA2731368C (en) | 2013-05-14 |
| EP2328890A1 (en) | 2011-06-08 |
| JP2011530500A (ja) | 2011-12-22 |
| ATE542813T1 (de) | 2012-02-15 |
| CA2731368A1 (en) | 2010-02-11 |
| EP2328890B1 (en) | 2012-01-25 |
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