CN102209711B - 用于治疗丙型肝炎的化合物 - Google Patents
用于治疗丙型肝炎的化合物 Download PDFInfo
- Publication number
- CN102209711B CN102209711B CN200980144810.1A CN200980144810A CN102209711B CN 102209711 B CN102209711 B CN 102209711B CN 200980144810 A CN200980144810 A CN 200980144810A CN 102209711 B CN102209711 B CN 102209711B
- Authority
- CN
- China
- Prior art keywords
- solvent
- fluorophenyl
- gradient
- pyridine
- mmol
- 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.)
- Expired - Fee Related
Links
- ZBVNXWBKKNJXSU-UHFFFAOYSA-N CC(C)(c1ccccc1)NC(c1cc(-c2cc3c(C(O)=O)c(-c(cc4)ccc4F)n[n]3cc2N(CCO)S(C)(=O)=O)ccc1)=O Chemical compound CC(C)(c1ccccc1)NC(c1cc(-c2cc3c(C(O)=O)c(-c(cc4)ccc4F)n[n]3cc2N(CCO)S(C)(=O)=O)ccc1)=O ZBVNXWBKKNJXSU-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)(c1ccccc1)NC(c1cc(-c2ccncc2N(CC*)S(C)(=O)=O)ccc1)=O Chemical compound CC(C)(c1ccccc1)NC(c1cc(-c2ccncc2N(CC*)S(C)(=O)=O)ccc1)=O 0.000 description 1
- LOWZRASZEBOGTC-UHFFFAOYSA-N CC(C)(c1ccccc1)NC(c1cccc(-c2cc3c(C(NC)=O)c(-c(cc4)ccc4F)n[n]3cc2NS(C)(=N)=O)c1)=O Chemical compound CC(C)(c1ccccc1)NC(c1cccc(-c2cc3c(C(NC)=O)c(-c(cc4)ccc4F)n[n]3cc2NS(C)(=N)=O)c1)=O LOWZRASZEBOGTC-UHFFFAOYSA-N 0.000 description 1
- UZNUPXTUWKSZCI-UHFFFAOYSA-N CCN(c(c(-c1ccccc1)cc1c2C(NC)=O)c[n]1nc2-c(cc1)ccc1F)S(C)(=O)=O Chemical compound CCN(c(c(-c1ccccc1)cc1c2C(NC)=O)c[n]1nc2-c(cc1)ccc1F)S(C)(=O)=O UZNUPXTUWKSZCI-UHFFFAOYSA-N 0.000 description 1
- MKNPLYKEDQXBSW-UHFFFAOYSA-N CCOC(c1c(-c(cc2)ccc2F)nc(cc2)[n]1cc2Br)=O Chemical compound CCOC(c1c(-c(cc2)ccc2F)nc(cc2)[n]1cc2Br)=O MKNPLYKEDQXBSW-UHFFFAOYSA-N 0.000 description 1
- GIGQRUJVNJBXDZ-UHFFFAOYSA-N CNC(c1c(ccc(-c(cccc2)c2OC)c2)[n]2nc1-c1ccccc1)=O Chemical compound CNC(c1c(ccc(-c(cccc2)c2OC)c2)[n]2nc1-c1ccccc1)=O GIGQRUJVNJBXDZ-UHFFFAOYSA-N 0.000 description 1
- ZVMKAOAHQZDGIY-UHFFFAOYSA-N Cc(c(-c1cc2c(C(NC)=O)c(-c(cc3)ccc3F)n[n]2c(C)c1)c1)ccc1C(NC1(CC1)c1ccccc1)=O Chemical compound Cc(c(-c1cc2c(C(NC)=O)c(-c(cc3)ccc3F)n[n]2c(C)c1)c1)ccc1C(NC1(CC1)c1ccccc1)=O ZVMKAOAHQZDGIY-UHFFFAOYSA-N 0.000 description 1
- WXKUXIOUHYOLCU-UHFFFAOYSA-N Cc(cc(c(C(NC1(CC1)C1CC1)=O)c1)OC)c1-c(cc[n](c1c2C(NC)=O)nc2-c(cc2)ccc2F)c1F Chemical compound Cc(cc(c(C(NC1(CC1)C1CC1)=O)c1)OC)c1-c(cc[n](c1c2C(NC)=O)nc2-c(cc2)ccc2F)c1F WXKUXIOUHYOLCU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/437—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 containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9600408P | 2008-09-11 | 2008-09-11 | |
| US61/096,004 | 2008-09-11 | ||
| PCT/US2009/055648 WO2010030538A2 (en) | 2008-09-11 | 2009-09-02 | Compounds for the treatment of hepatitis c |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410060239.8A Division CN103864783A (zh) | 2008-09-11 | 2009-09-02 | 用于治疗丙型肝炎的化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102209711A CN102209711A (zh) | 2011-10-05 |
| CN102209711B true CN102209711B (zh) | 2014-06-18 |
Family
ID=41203516
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980144810.1A Expired - Fee Related CN102209711B (zh) | 2008-09-11 | 2009-09-02 | 用于治疗丙型肝炎的化合物 |
| CN201410060239.8A Pending CN103864783A (zh) | 2008-09-11 | 2009-09-02 | 用于治疗丙型肝炎的化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410060239.8A Pending CN103864783A (zh) | 2008-09-11 | 2009-09-02 | 用于治疗丙型肝炎的化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8198449B2 (https=) |
| EP (1) | EP2331502B1 (https=) |
| JP (1) | JP2012502099A (https=) |
| KR (1) | KR20110056537A (https=) |
| CN (2) | CN102209711B (https=) |
| AR (1) | AR073586A1 (https=) |
| AU (1) | AU2009291993A1 (https=) |
| MX (1) | MX2011002471A (https=) |
| TW (1) | TW201014855A (https=) |
| WO (1) | WO2010030538A2 (https=) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101774035B1 (ko) | 2009-10-30 | 2017-09-01 | 얀센 파마슈티카 엔.브이. | 이미다조［１，２―ｂ］피리다진 유도체 및 ＰＤＥ１０ 저해제로서의 그의 용도 |
| EP2496578A4 (en) * | 2009-11-05 | 2013-08-21 | Univ Notre Dame Du Lac | IMIDAZO [1,2-A] PYRIDINE COMPOUNDS, THEIR SYNTHESIS AND METHODS OF USE THEREOF |
| FR2953520B1 (fr) * | 2009-12-04 | 2011-11-25 | Sanofi Aventis | Derives de diphenyl-pyrazolopyridines, leur preparation et leur application en therapeutique |
| US8324212B2 (en) * | 2010-02-25 | 2012-12-04 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| 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 |
| WO2011112186A1 (en) * | 2010-03-10 | 2011-09-15 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis c |
| US8354410B2 (en) | 2010-03-11 | 2013-01-15 | Bristol-Meyers Squibb Company | Compounds for the treatment of hepatitis C |
| AR082453A1 (es) * | 2010-04-21 | 2012-12-12 | Novartis Ag | Compuestos de furopiridina, composiciones farmaceuticas que los contienen y usos de los mismos |
| US8445497B2 (en) | 2010-06-30 | 2013-05-21 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| SG189882A1 (en) * | 2010-10-20 | 2013-06-28 | Biota Scient Management | Viral polymerase inhibitors |
| SG189985A1 (en) | 2010-10-26 | 2013-06-28 | Presidio Pharmaceuticals Inc | Inhibitors of hepatitis c virus |
| CA2822357A1 (en) | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| WO2013000924A1 (en) | 2011-06-27 | 2013-01-03 | Janssen Pharmaceutica Nv | 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES |
| WO2013030750A1 (en) | 2011-09-01 | 2013-03-07 | Lupin Limited | Antiviral compounds |
| US9303020B2 (en) | 2012-02-08 | 2016-04-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| AU2013217224B2 (en) | 2012-02-10 | 2017-04-06 | Lupin Limited | Antiviral compounds with a dibenzooxaheterocycle moiety |
| WO2013148620A1 (en) | 2012-03-27 | 2013-10-03 | Bristol-Myers Squibb Company | Benzofuran derivatives for the treatment of hepatitis c |
| WO2013152392A1 (en) | 2012-04-11 | 2013-10-17 | Biota Scientific Management Pty Ltd | Viral polymerase inhibitors |
| WO2013163466A1 (en) * | 2012-04-25 | 2013-10-31 | Presidio Pharmaceuticals, Inc. | Inhibitors of hepatitis c virus |
| CN102690264B (zh) * | 2012-06-20 | 2014-07-02 | 泰山医学院 | 2-苯基-3-取代咪唑并[1,2-a]吡啶类衍生物及其制备方法 |
| 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 |
| US8778964B2 (en) | 2012-11-05 | 2014-07-15 | Bayer Pharma Aktiengesellschaft | Hydroxy-substituted imidazo[1,2-a]-pyridinecarboxamides and their use |
| US8796305B2 (en) | 2012-11-05 | 2014-08-05 | Bayer Pharma Aktiengesellschaft | Carboxy-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US9624214B2 (en) | 2012-11-05 | 2017-04-18 | Bayer Pharma Aktiengesellschaft | Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US9126998B2 (en) | 2012-11-05 | 2015-09-08 | Bayer Pharma AG | Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US8871754B2 (en) | 2012-11-19 | 2014-10-28 | Irm Llc | Compounds and compositions for the treatment of parasitic diseases |
| LT2925757T (lt) | 2012-11-19 | 2017-12-27 | Novartis Ag | Junginiai ir kompozicijos, skirti parazitinių ligų gydymui |
| US8962651B2 (en) * | 2013-03-13 | 2015-02-24 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US9776997B2 (en) | 2013-06-04 | 2017-10-03 | Bayer Pharma Aktiengesellschaft | 3-aryl-substituted imidazo[1,2-A]pyridines and their use |
| TW201609651A (zh) * | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（一） |
| US9688699B2 (en) | 2014-02-19 | 2017-06-27 | Bayer Pharma Aktiengesellschaft | 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines |
| CN106715426A (zh) | 2014-03-21 | 2017-05-24 | 拜耳医药股份有限公司 | 氰基取代的咪唑并[1,2‑a]吡啶甲酰胺及其用途 |
| AR099820A1 (es) * | 2014-03-21 | 2016-08-17 | Bristol Myers Squibb Co | Ciano que contiene compuestos de azabenzofuran para el tratamiento de la hepatitis c |
| US9920036B2 (en) * | 2014-03-21 | 2018-03-20 | Bristol-Myers Squibb Company | Cyanoamino (aza)benzofuran compounds for the treatment of hepatitis C |
| CN106459037A (zh) | 2014-05-02 | 2017-02-22 | 拜耳医药股份有限公司 | 用于治疗心血管疾病的N‑(2‑氨基‑5‑氟‑2‑甲基戊基)‑8‑[(2,6‑二氟苄基)氧基]‑2‑甲基咪唑并[1,2‑a]吡啶‑3‑甲酰胺的对映异构体及其二‑和三氟衍生物的对映异构体 |
| EP3180346A1 (en) * | 2014-08-05 | 2017-06-21 | Bristol-Myers Squibb Company | Furopyridine compounds for the treatment of hepatitis c |
| JP2017529401A (ja) * | 2014-09-26 | 2017-10-05 | チャーンジョウ インシュヨン ファーマシューティカル カンパニー，リミティド | Ｎｓ４ｂ阻害剤としてのベンゾフラン類似体 |
| EP3227287B1 (de) | 2014-12-02 | 2019-08-07 | Bayer Pharma Aktiengesellschaft | Heteroaryl-substituierte imidazo[1,2-a]pyridine und ihre verwendung |
| CN108348510B (zh) | 2015-09-17 | 2022-01-04 | 圣母大学 | 针对分枝杆菌感染有用的含有苄胺的杂环化合物以及组合物 |
| WO2018184976A1 (de) | 2017-04-05 | 2018-10-11 | Bayer Pharma Aktiengesellschaft | Substituierte imidazo[1,2-a]pyridincarboxamide und ihre verwendung |
| RU2019123849A (ru) * | 2019-07-29 | 2021-02-01 | Дзе Брихэм Энд Уимен`З Хоспитал, Инк. | Ингибиторы фактора ингибирования миграции макрофагов |
| WO2024102699A1 (en) * | 2022-11-07 | 2024-05-16 | ELANCO US, Inc. | Guanylate cyclase (gc) stimulator formulations and uses thereof |
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| WO2009137493A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 2-substituted benzofuran compounds to treat infection with hepatitis c virus |
| US7994171B2 (en) * | 2008-09-11 | 2011-08-09 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8048887B2 (en) * | 2008-09-11 | 2011-11-01 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
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2009
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- 2009-09-02 KR KR1020117008086A patent/KR20110056537A/ko not_active Withdrawn
- 2009-09-02 JP JP2011526911A patent/JP2012502099A/ja active Pending
- 2009-09-02 EP EP09792143.1A patent/EP2331502B1/en not_active Not-in-force
- 2009-09-02 WO PCT/US2009/055648 patent/WO2010030538A2/en not_active Ceased
- 2009-09-02 AU AU2009291993A patent/AU2009291993A1/en not_active Abandoned
- 2009-09-02 CN CN200980144810.1A patent/CN102209711B/zh not_active Expired - Fee Related
- 2009-09-02 MX MX2011002471A patent/MX2011002471A/es active IP Right Grant
- 2009-09-02 CN CN201410060239.8A patent/CN103864783A/zh active Pending
- 2009-09-11 AR ARP090103513A patent/AR073586A1/es not_active Application Discontinuation
- 2009-09-11 TW TW098130826A patent/TW201014855A/zh unknown
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2012
- 2012-05-14 US US13/470,727 patent/US8536338B2/en active Active
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|---|---|---|---|---|
| WO2002016359A1 (en) * | 2000-08-22 | 2002-02-28 | Glaxo Group Limited | Fused pyrazole derivatives being protein kinase inhibitors |
| WO2002078701A1 (en) * | 2001-03-30 | 2002-10-10 | Smithkline Beecham Corporation | Use of pyrazolopyridines as therapeutic compounds |
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| Title |
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| Acid-Catalyzed Reactions of 3-(Hydroxymethyl)- and 3-(1-hydroxyethyl)pyrazolo[1,5-a]pyridines;Yasuyoshi Miki，et al.;《Journal of Heterocyclic Chemistry》;19891231;第26卷(第6期);1739-1745 * |
| Preparation of New Nitrogen-Bridged Heterocycles. XIV. Further Investigation of the Desulfurization and the Rearrangement of Pyrido[1,2-d]-1,3,4-thiadiazine Intermediates;AKIKAZU KAKEHI，et al.;《Chemical & Pharmaceutical Bulletin》;19871231;第35卷(第1期);156-169 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2331502B1 (en) | 2016-03-02 |
| WO2010030538A2 (en) | 2010-03-18 |
| US20120232099A1 (en) | 2012-09-13 |
| TW201014855A (en) | 2010-04-16 |
| AR073586A1 (es) | 2010-11-17 |
| MX2011002471A (es) | 2011-04-05 |
| JP2012502099A (ja) | 2012-01-26 |
| US8536338B2 (en) | 2013-09-17 |
| KR20110056537A (ko) | 2011-05-30 |
| EP2331502A2 (en) | 2011-06-15 |
| AU2009291993A1 (en) | 2010-03-18 |
| US8198449B2 (en) | 2012-06-12 |
| US20100063068A1 (en) | 2010-03-11 |
| WO2010030538A3 (en) | 2010-05-06 |
| CN102209711A (zh) | 2011-10-05 |
| CN103864783A (zh) | 2014-06-18 |
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