JP2013526539A - Atrキナーゼ阻害剤として有用なピラジン - Google Patents
Atrキナーゼ阻害剤として有用なピラジン Download PDFInfo
- Publication number
- JP2013526539A JP2013526539A JP2013510296A JP2013510296A JP2013526539A JP 2013526539 A JP2013526539 A JP 2013526539A JP 2013510296 A JP2013510296 A JP 2013510296A JP 2013510296 A JP2013510296 A JP 2013510296A JP 2013526539 A JP2013526539 A JP 2013526539A
- Authority
- JP
- Japan
- Prior art keywords
- aliphatic
- compound
- cancer
- compound according
- alkyl
- 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.)
- Pending
Links
- 0 *c1ncc(N)nc1C(Nc1ccccc1)=O Chemical compound *c1ncc(N)nc1C(Nc1ccccc1)=O 0.000 description 1
- FBYUCYIVLCKFGO-ONEGZZNKSA-N C/C=C/c(nc1-c2nc(ccc(C)c3)c3[nH]2)cnc1N Chemical compound C/C=C/c(nc1-c2nc(ccc(C)c3)c3[nH]2)cnc1N FBYUCYIVLCKFGO-ONEGZZNKSA-N 0.000 description 1
- ATRCFFDRJPZWFK-UHFFFAOYSA-N CN(CC1)CCN1c1cc(Nc2nc(C(Nc3ccccc3)=O)c(N)nc2)ccc1 Chemical compound CN(CC1)CCN1c1cc(Nc2nc(C(Nc3ccccc3)=O)c(N)nc2)ccc1 ATRCFFDRJPZWFK-UHFFFAOYSA-N 0.000 description 1
- INCSQLZZXBPATR-UHFFFAOYSA-N COC(c1c(N)nccn1)=O Chemical compound COC(c1c(N)nccn1)=O INCSQLZZXBPATR-UHFFFAOYSA-N 0.000 description 1
- CNXSIRHOIFRMOB-UHFFFAOYSA-N COC(c1nc(Br)cnc1N)=O Chemical compound COC(c1nc(Br)cnc1N)=O CNXSIRHOIFRMOB-UHFFFAOYSA-N 0.000 description 1
- UWHOUQGLFIVGKW-UHFFFAOYSA-N Cc(cc1)cc2c1nc(-c1nc(NC(CC#N)=O)cnc1N)[nH]2 Chemical compound Cc(cc1)cc2c1nc(-c1nc(NC(CC#N)=O)cnc1N)[nH]2 UWHOUQGLFIVGKW-UHFFFAOYSA-N 0.000 description 1
- CAELIUDQACEMGX-UHFFFAOYSA-N Cc(nc1)c(C(Nc(cccc2)c2OC)=O)nc1N Chemical compound Cc(nc1)c(C(Nc(cccc2)c2OC)=O)nc1N CAELIUDQACEMGX-UHFFFAOYSA-N 0.000 description 1
- XWCYVCRFSFOMDJ-UHFFFAOYSA-N Cc1ccc2nc(-c3nc(Br)cnc3N)[nH]c2c1 Chemical compound Cc1ccc2nc(-c3nc(Br)cnc3N)[nH]c2c1 XWCYVCRFSFOMDJ-UHFFFAOYSA-N 0.000 description 1
- JZNWUXZWEPEKHO-UHFFFAOYSA-N Nc(c(-c1nc2ccccc2[nH]1)n1)ncc1Sc1cccc(F)c1 Chemical compound Nc(c(-c1nc2ccccc2[nH]1)n1)ncc1Sc1cccc(F)c1 JZNWUXZWEPEKHO-UHFFFAOYSA-N 0.000 description 1
- RSFJAMFLTSNZHU-UHFFFAOYSA-N Nc(c(C(NNC(c1ccccc1)=O)=O)n1)ncc1Br Chemical compound Nc(c(C(NNC(c1ccccc1)=O)=O)n1)ncc1Br RSFJAMFLTSNZHU-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N Nc1ccccn1 Chemical compound Nc1ccccn1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- 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
- C07D241/24—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
- 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
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33385210P | 2010-05-12 | 2010-05-12 | |
| US61/333,852 | 2010-05-12 | ||
| PCT/US2011/036239 WO2011143419A1 (en) | 2010-05-12 | 2011-05-12 | Pyrazines useful as inhibitors of atr kinase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013526539A true JP2013526539A (ja) | 2013-06-24 |
| JP2013526539A5 JP2013526539A5 (enExample) | 2014-06-26 |
Family
ID=44628457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013510296A Pending JP2013526539A (ja) | 2010-05-12 | 2011-05-12 | Atrキナーゼ阻害剤として有用なピラジン |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8962631B2 (enExample) |
| EP (1) | EP2569289A1 (enExample) |
| JP (1) | JP2013526539A (enExample) |
| WO (1) | WO2011143419A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020217733A1 (ja) * | 2019-04-26 | 2020-10-29 | 株式会社カネカ | Vadadustat中間体の製造方法 |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2743134A1 (en) | 2008-11-10 | 2010-05-14 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| ES2921576T3 (es) | 2008-12-19 | 2022-08-29 | Vertex Pharma | Compuestos útiles como inhibidores de la quinasa ATR |
| US9062008B2 (en) | 2010-05-12 | 2015-06-23 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US9334244B2 (en) | 2010-05-12 | 2016-05-10 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US8962631B2 (en) | 2010-05-12 | 2015-02-24 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| NZ603477A (en) | 2010-05-12 | 2014-09-26 | Vertex Pharma | Compounds useful as inhibitors of atr kinase |
| EP2568984A1 (en) | 2010-05-12 | 2013-03-20 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| CA2798760A1 (en) | 2010-05-12 | 2011-11-17 | Vertex Pharmaceuticals Incorporated | 2-aminopyridine derivatives useful as inhibitors of atr kinase |
| MX2013000103A (es) | 2010-06-23 | 2013-06-13 | Vertex Pharma | Derivados de pirrolo-pirazina utiles como inhibidores de cinasa art. |
| MX2013011450A (es) | 2011-04-05 | 2014-02-03 | Vertex Pharma | Compuestos de aminopirazina utiles como inhibidores de la cinasa ataxia telangiectasia mutada y rad3 relacionados (atr). |
| US8822469B2 (en) | 2011-06-22 | 2014-09-02 | Vertex Pharmaceuticals Incorporated | Pyrrolo[2,3-B]pyrazines useful as inhibitors of ATR kinase |
| US9309250B2 (en) | 2011-06-22 | 2016-04-12 | Vertex Pharmaceuticals Incorporated | Substituted pyrrolo[2,3-b]pyrazines as ATR kinase inhibitors |
| EP2723747A1 (en) | 2011-06-22 | 2014-04-30 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of atr kinase |
| WO2013049720A1 (en) | 2011-09-30 | 2013-04-04 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| WO2013049722A1 (en) | 2011-09-30 | 2013-04-04 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| CN108685922A (zh) | 2011-09-30 | 2018-10-23 | 沃泰克斯药物股份有限公司 | 用atr抑制剂治疗胰腺癌和非小细胞肺癌 |
| CN106496173A (zh) | 2011-09-30 | 2017-03-15 | 沃泰克斯药物股份有限公司 | 用于制备可用作atr激酶抑制剂的化合物的方法 |
| US8765751B2 (en) | 2011-09-30 | 2014-07-01 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| JP2015502925A (ja) | 2011-11-09 | 2015-01-29 | 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ピラジン化合物 |
| US8841450B2 (en) | 2011-11-09 | 2014-09-23 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US8846918B2 (en) | 2011-11-09 | 2014-09-30 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US8846917B2 (en) | 2011-11-09 | 2014-09-30 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US8841337B2 (en) | 2011-11-09 | 2014-09-23 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| CN108478577A (zh) | 2012-04-05 | 2018-09-04 | 沃泰克斯药物股份有限公司 | 可用作atr激酶抑制剂的化合物及其组合疗法 |
| US8859553B2 (en) * | 2012-07-30 | 2014-10-14 | Astar Biotech Llc | Protein kinase inhibitors |
| DK2904406T3 (en) | 2012-10-04 | 2018-06-18 | Vertex Pharma | METHOD OF DETERMINING THE ATR INHIBITION, INCREASED DNA DAMAGE |
| EP2909202A1 (en) | 2012-10-16 | 2015-08-26 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| SI2941432T1 (en) | 2012-12-07 | 2018-07-31 | Vertex Pharmaceuticals Incorporated | 2-AMINO-6-FLUORO-N- (5-FLUORO-4- (4- (4- (OXETHAN-3-YL) PIPERAZIN-1-CARBONYL) PIPERIDIN-1-YLIPRIDIN-3-YL) 1,5 ALFA) PYRIMIDINE-3-CARBOXAMIDE AS ATR KINAZE INHIBITOR |
| CN105164107B (zh) * | 2012-12-20 | 2017-12-05 | 卢庆彬 | 用于与放射结合使用的放射增敏剂化合物 |
| WO2014143240A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Fused pyrazolopyrimidine derivatives useful as inhibitors of atr kinase |
| PT3077397T (pt) | 2013-12-06 | 2020-01-22 | Vertex Pharma | Composto de 2-amino-6-fluoro-n-[5-fluoro-piridin-3-il]pirazolo[1,5-a]pirimidin-3-carboxamida útil como inibidor da atr quinase, a sua preparação, diferentes formas sólidas e derivados radiomarcados do mesmo |
| MX373102B (es) | 2014-06-05 | 2020-04-17 | Vertex Pharma | Derivados radiomarcados de un compuesto de 2-amino-6-fluoro-n-[5-fluoro-piridin-3-il]-pirazolo[1,5-a]pirimidin-3-carboxamida útil como inhibidor de ataxia telangiectasia mutada y rad3 relacionado (atr) cinasa, preparación de tal compuesto y diferentes formas sólidas del mismo. |
| SG11201610500WA (en) | 2014-06-17 | 2017-01-27 | Vertex Pharma | Method for treating cancer using a combination of chk1 and atr inhibitors |
| TWI656121B (zh) | 2014-08-04 | 2019-04-11 | 德商拜耳製藥公司 | 2-(嗎啉-4-基)-1,7-萘啶 |
| WO2016207345A1 (en) * | 2015-06-24 | 2016-12-29 | Pierre Fabre Medicament | 3-amino-pyrazin-2-yl carboxamide and 2-amino-pyridin-3-yl carboxamide derivatives as polo-like kinase 1 (plk-1) inhibitors for the treatment of cancer |
| AU2016331955B2 (en) | 2015-09-30 | 2022-07-21 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
| MX2018008507A (es) | 2016-01-11 | 2019-07-04 | Merrimack Pharmaceuticals Inc | Inhibición de proteína relacionada con ataxia telangiectasia y rad3 (atr). |
| JOP20190197A1 (ar) | 2017-02-24 | 2019-08-22 | Bayer Pharma AG | مثبط كيناز ايه تي آر للاستخدام في طريقة لعلاج مرض فرط التكاثر |
| WO2018153972A1 (en) | 2017-02-24 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Combination of atr kinase inhibitors and antiandrogens |
| TW201840319A (zh) | 2017-02-24 | 2018-11-16 | 德商拜耳廠股份有限公司 | Atr激酶抑制劑與鐳-223鹽之組合 |
| WO2018206547A1 (en) | 2017-05-12 | 2018-11-15 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and atr inhibitors |
| WO2018218197A2 (en) * | 2017-05-26 | 2018-11-29 | Board Of Regents, The University Of Texas System | Tetrahydropyrido[4,3-d]pyrimidine inhibitors of atr kinase |
| US10377591B2 (en) | 2017-07-07 | 2019-08-13 | Zebra Technologies Corporation | Input handling for media processing devices |
| WO2019014618A1 (en) | 2017-07-13 | 2019-01-17 | Board Of Regents, University Of Texas System | HETEROCYCLIC INHIBITORS OF KINASE ATR |
| US11690911B2 (en) | 2017-08-04 | 2023-07-04 | Bayer Aktiengesellschaft | Combination of ATR kinase inhibitors and PD-1/PD-L1 inhibitors |
| EP3461480A1 (en) | 2017-09-27 | 2019-04-03 | Onxeo | Combination of a dna damage response cell cycle checkpoint inhibitors and belinostat for treating cancer |
| SG11202003879RA (en) | 2017-10-30 | 2020-05-28 | Neuropore Therapies Inc | Substituted phenyl sulfonyl phenyl triazole thiones and uses thereof |
| EP3720973A1 (en) | 2017-12-08 | 2020-10-14 | Bayer Aktiengesellschaft | Predictive markers for atr kinase inhibitors |
| JP7341156B2 (ja) | 2018-03-16 | 2023-09-08 | ボード オブ レジェンツ,ザ ユニバーシティ オブ テキサス システム | Atrキナーゼの複素環式阻害剤 |
| KR20210066837A (ko) | 2018-09-26 | 2021-06-07 | 메르크 파텐트 게엠베하 | 암 치료를 위한 pd-1 안타고니스트, atr 억제제 및 백금화제의 조합 |
| WO2020078905A1 (en) | 2018-10-15 | 2020-04-23 | Merck Patent Gmbh | Combination therapy utilizing dna alkylating agents and atr inhibitors |
| WO2020078788A1 (en) | 2018-10-16 | 2020-04-23 | Bayer Aktiengesellschaft | Combination of atr kinase inhibitors with 2,3-dihydroimidazo[1,2-c]quinazoline compounds |
| CA3181279A1 (en) | 2022-03-24 | 2023-09-24 | Bloom Energy Corporation | Fuel cell stack assembly including heat sink inserts |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003516974A (ja) * | 1999-12-17 | 2003-05-20 | カイロン コーポレイション | グリコーゲンシンターゼキナーゼ3のピラジンベースインヒビター |
| JP2006520794A (ja) * | 2003-03-21 | 2006-09-14 | スミスクライン ビーチャム コーポレーション | 化合物 |
| JP2006521357A (ja) * | 2003-03-24 | 2006-09-21 | メルク エンド カムパニー インコーポレーテッド | ナトリウムチャンネル遮断薬としてのビアリール置換6員複素環化合物 |
| WO2006124874A2 (en) * | 2005-05-12 | 2006-11-23 | Kalypsys, Inc. | Inhibitors of b-raf kinase |
| JP2007524682A (ja) * | 2004-02-12 | 2007-08-30 | メルク エンド カムパニー インコーポレーテッド | 代謝調節型グルタミン酸受容体−5の調節物質としてのビピリジルアミド |
| WO2008156174A1 (ja) * | 2007-06-21 | 2008-12-24 | Taisho Pharmaceutical Co., Ltd. | ピラジンアミド化合物 |
| WO2009037247A1 (en) * | 2007-09-17 | 2009-03-26 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
| JP2009541247A (ja) * | 2006-06-19 | 2009-11-26 | エフ.ホフマン−ラ ロシュ アーゲー | 2−ピラジンカルボキシアミド誘導体 |
| JP2012508260A (ja) * | 2008-11-10 | 2012-04-05 | 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キナーゼの阻害剤として有用な化合物 |
| JP2014518545A (ja) * | 2011-03-04 | 2014-07-31 | ローカス ファーマシューティカルズ インコーポレイテッド | アミノピラジン化合物 |
Family Cites Families (121)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4309430A (en) | 1980-06-27 | 1982-01-05 | Merck & Co., Inc. | Pyrazinyl-1,2,4-oxadiazole-5-ones, for treatment of edema, and processes for preparing same |
| US5329012A (en) | 1987-10-29 | 1994-07-12 | The Research Foundation Of State University Of New York | Bis(acyloxmethyl)imidazole compounds |
| JP2597917B2 (ja) | 1990-04-26 | 1997-04-09 | 富士写真フイルム株式会社 | 新規な色素形成カプラー及びそれを用いたハロゲン化銀カラー写真感光材料 |
| JP2002241379A (ja) | 1997-03-21 | 2002-08-28 | Dainippon Pharmaceut Co Ltd | 3−オキサジアゾリルキノキサリン誘導体 |
| AU748816B2 (en) | 1998-07-16 | 2002-06-13 | Shionogi & Co., Ltd. | Pyrimidine derivatives exhibiting antitumor activity |
| US6660753B2 (en) | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| US6849660B1 (en) | 2000-08-01 | 2005-02-01 | Isis Pharmaceuticals, Inc. | Antimicrobial biaryl compounds |
| EP1217000A1 (en) | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| ATE409181T1 (de) | 2001-05-08 | 2008-10-15 | Univ Yale | Proteomimetische verbindungen und verfahren |
| SE0102438D0 (sv) | 2001-07-05 | 2001-07-05 | Astrazeneca Ab | New compounds |
| SE0102439D0 (sv) | 2001-07-05 | 2001-07-05 | Astrazeneca Ab | New compounds |
| BR0214309A (pt) | 2001-11-21 | 2004-10-13 | Upjohn Co | Derivados aril-1,4-pirazina substituìdos |
| US6992087B2 (en) | 2001-11-21 | 2006-01-31 | Pfizer Inc | Substituted aryl 1,4-pyrazine derivatives |
| WO2003066629A2 (en) | 2002-02-06 | 2003-08-14 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds useful as inhibitors of gsk-3 |
| CN100445276C (zh) | 2002-03-13 | 2008-12-24 | 詹森药业有限公司 | 用作组蛋白去乙酰酶抑制剂的磺酰基衍生物 |
| GB0206860D0 (en) | 2002-03-22 | 2002-05-01 | Glaxo Group Ltd | Compounds |
| TWI319387B (en) | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
| GB0209715D0 (en) | 2002-04-27 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| US7704995B2 (en) | 2002-05-03 | 2010-04-27 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| EP1501514B1 (en) | 2002-05-03 | 2012-12-19 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| US7429609B2 (en) | 2002-05-31 | 2008-09-30 | Eisai R & D Management Co., Ltd. | Pyrazole compound and medicinal composition containing the same |
| AU2003249369A1 (en) | 2002-06-21 | 2004-01-06 | Cellular Genomics, Inc. | Certain amino-substituted monocycles as kinase modulators |
| AU2003282679A1 (en) | 2002-10-04 | 2004-05-04 | Arena Pharmaceuticals, Inc. | Hydroxypyrazoles for use against metabolic-related disorders |
| SE0203752D0 (sv) | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| SE0203754D0 (sv) | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| WO2004080982A1 (en) | 2003-03-11 | 2004-09-23 | Pfizer Products Inc. | Pyrazine compounds as transforming growth factor (tgf) inhibitors |
| GB2400101A (en) | 2003-03-28 | 2004-10-06 | Biofocus Discovery Ltd | Compounds capable of binding to the active site of protein kinases |
| AU2004240586A1 (en) | 2003-05-15 | 2004-12-02 | Merck & Co., Inc. | 3-(2-amino-1-azacyclyl)-5-aryl-1,2,4-oxadiazoles as S1P receptor agonists |
| TWI339206B (en) | 2003-09-04 | 2011-03-21 | Vertex Pharma | Compositions useful as inhibitors of protein kinases |
| WO2005034952A2 (en) | 2003-10-07 | 2005-04-21 | The Feinstein Institute For Medical Research | Isoxazole and isothiazole compounds useful in the treatment of inflammation |
| JP2008502687A (ja) | 2004-06-14 | 2008-01-31 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| CA2573573A1 (en) | 2004-07-27 | 2006-02-09 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| US7626021B2 (en) | 2004-07-27 | 2009-12-01 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| EP1828144A2 (en) | 2004-11-12 | 2007-09-05 | OSI Pharmaceuticals, Inc. | Integrin antagonists useful as anticancer agents |
| WO2006058120A1 (en) | 2004-11-22 | 2006-06-01 | Vertex Pharmaceuticals Incorporated | Bicyclic inhibitors or rho kinase |
| GB0428235D0 (en) | 2004-12-23 | 2005-01-26 | Glaxo Group Ltd | Novel compounds |
| MX2007007797A (es) | 2004-12-27 | 2007-08-23 | Alcon Inc | Analogo de aminopirazina para tratar glaucoma y otras enfermedades mediadas por rho cinasa. |
| GB0500492D0 (en) | 2005-01-11 | 2005-02-16 | Cyclacel Ltd | Compound |
| US7622583B2 (en) | 2005-01-14 | 2009-11-24 | Chemocentryx, Inc. | Heteroaryl sulfonamides and CCR2 |
| GB0501999D0 (en) | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| JP4873352B2 (ja) | 2005-02-16 | 2012-02-08 | シェーリング コーポレイション | Cxcr3アンタゴニスト活性を有する、複素環で置換されたピペラジン |
| WO2006114180A1 (de) | 2005-04-25 | 2006-11-02 | Merck Patent Gmbh | Neuartige aza-heterozyklen als kinase-inhibitoren |
| WO2007015632A1 (en) | 2005-08-04 | 2007-02-08 | Cgk Co., Ltd. | Atm and atr inhibitor |
| AR056786A1 (es) | 2005-11-10 | 2007-10-24 | Smithkline Beecham Corp | Compuesto de 1h- imidazo ( 4,5-c) piridin-2-ilo, composicion farmaceutica que lo comprende, procedimiento para preparar dicha composicion, su uso para preparar unmedicamento, uso de una combinacion que omprende al compuesto y al menos un agente antineoplasico para preparar un medicamento y dicha com |
| EP1959951B1 (en) | 2005-12-01 | 2009-12-23 | F. Hoffmann-la Roche AG | Heteroaryl substituted piperidine derivatives as l-cpt1 inhibitors |
| EP1970377A4 (en) | 2005-12-09 | 2013-02-27 | Meiji Seika Kaisha | LINCOMYCIN DERIVATIVE AND ANTIBACTERIAL AGENT CONTAINING THIS AS AN ACTIVE SUBSTANCE |
| MX2008008328A (es) | 2005-12-22 | 2008-09-15 | Alcon Res Ltd | (indazol-5-il)-pirazinas y (1,3-dihidro-indol-2-ona)-pirazinas para tratar enfermedades y condiciones mediadas con rho cinasa. |
| ITMI20060311A1 (it) | 2006-02-21 | 2007-08-22 | Btsr Int Spa | Dispositivo perfezionato di alimentazione di filo o filatio ad una macchina tessile e metodo per attuare tale alimentazione |
| GB0603684D0 (en) | 2006-02-23 | 2006-04-05 | Novartis Ag | Organic compounds |
| WO2007096764A2 (en) | 2006-02-27 | 2007-08-30 | Glenmark Pharmaceuticals S.A. | Bicyclic heteroaryl derivatives as cannabinoid receptor modulators |
| TW200800203A (en) | 2006-03-08 | 2008-01-01 | Astrazeneca Ab | New use |
| JP2009533327A (ja) | 2006-03-22 | 2009-09-17 | 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 | 増殖性疾患を処置するためのc−METキナーゼ阻害剤 |
| MX2008012658A (es) | 2006-03-31 | 2008-12-16 | Schering Corp | Inhibidores de cinasa. |
| EP2038261A2 (en) | 2006-06-22 | 2009-03-25 | Mallinckrodt Inc. | Pyrazine derivatives with extended conjugation and uses thereof |
| US20080039450A1 (en) | 2006-06-22 | 2008-02-14 | Jensen Annika J | Compounds |
| WO2008037477A1 (en) | 2006-09-29 | 2008-04-03 | Novartis Ag | Pyrazolopyrimidines as p13k lipid kinase inhibitors |
| GB0619342D0 (en) | 2006-09-30 | 2006-11-08 | Vernalis R&D Ltd | New chemical compounds |
| KR101107896B1 (ko) | 2006-10-04 | 2012-01-25 | 에프. 호프만-라 로슈 아게 | 고 밀도 지단백질(hdl)-콜레스테롤 상승제로서 3-피리딘카복스아마이드 및 2-피라진카복스아마이드 유도체 |
| MX337906B (es) | 2006-10-19 | 2016-03-28 | Signal Pharm Llc | Compuestos de heteroarilo, composiciones de los mismos, y su uso como inhibidores de proteina cinasas. |
| US8148361B2 (en) | 2006-11-10 | 2012-04-03 | Bristol-Myers Squibb Company | Kinase inhibitors |
| EP2125808A2 (en) | 2006-12-15 | 2009-12-02 | Bayer Schering Pharma Aktiengesellschaft | 3-h-pyrazolopyridines and salts thereof, pharmaceutical compositions comprising same, methods of preparing same and uses of same |
| AU2007338792B2 (en) | 2006-12-20 | 2012-05-31 | Amgen Inc. | Substituted heterocycles and methods of use |
| PE20121126A1 (es) | 2006-12-21 | 2012-08-24 | Plexxikon Inc | Compuestos pirrolo [2,3-b] piridinas como moduladores de quinasa |
| GB0625659D0 (en) | 2006-12-21 | 2007-01-31 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| MX2009008531A (es) | 2007-02-16 | 2009-08-26 | Amgen Inc | Cetonas de heterociclilo que contienen nitrogeno y su uso como inhibidores de c-met. |
| CA2679659C (en) | 2007-03-01 | 2016-01-19 | Novartis Ag | Pim kinase inhibitors and methods of their use |
| US8372867B2 (en) | 2007-04-10 | 2013-02-12 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
| PE20090288A1 (es) | 2007-05-10 | 2009-04-03 | Smithkline Beecham Corp | Derivados de quinoxalina como inhibidores de la pi3 quinasa |
| PE20090717A1 (es) | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| UY31137A1 (es) | 2007-06-14 | 2009-01-05 | Smithkline Beecham Corp | Derivados de quinazolina como inhibidores de la pi3 quinasa |
| EP2170306A1 (en) | 2007-06-26 | 2010-04-07 | Lexicon Pharmaceuticals, Inc. | Methods of treating serotonin-mediated diseases and disorders |
| GB0713259D0 (en) | 2007-07-09 | 2007-08-15 | Astrazeneca Ab | Pyrazine derivatives 954 |
| HRP20151052T1 (xx) | 2007-07-19 | 2015-11-06 | H. Lundbeck A/S | Peteroäślani heterocikliäśki amidi i srodne tvari |
| MY150032A (en) | 2007-07-19 | 2013-11-29 | Merck Sharp & Dohme | Heterocyclic amide compounds as protein kinase inhibitors |
| WO2009016460A2 (en) | 2007-08-01 | 2009-02-05 | Pfizer Inc. | Pyrazole compounds and their use as raf inhibitors |
| WO2009024825A1 (en) | 2007-08-21 | 2009-02-26 | Astrazeneca Ab | 2-pyrazinylbenzimidazole derivatives as receptor tyrosine kinase inhibitors |
| JP2011500778A (ja) * | 2007-10-25 | 2011-01-06 | アストラゼネカ・アクチエボラーグ | ピリジン及びピラジン誘導体−083 |
| CA2712507A1 (en) | 2008-02-25 | 2009-09-03 | F. Hoffmann-La Roche Ag | Pyrrolopyrazine kinase inhibitors |
| CN101945877B (zh) | 2008-02-25 | 2013-07-03 | 霍夫曼-拉罗奇有限公司 | 吡咯并吡嗪激酶抑制剂 |
| JP5368485B2 (ja) | 2008-02-25 | 2013-12-18 | エフ.ホフマン−ラ ロシュ アーゲー | ピロロピラジンキナーゼインヒビター |
| WO2009106444A1 (en) | 2008-02-25 | 2009-09-03 | F. Hoffmann-La Roche Ag | Pyrrolopyrazine kinase inhibitors |
| TW200940537A (en) | 2008-02-26 | 2009-10-01 | Astrazeneca Ab | Heterocyclic urea derivatives and methods of use thereof |
| US8110576B2 (en) | 2008-06-10 | 2012-02-07 | Plexxikon Inc. | Substituted pyrrolo[2,3b]pyrazines and methods for treatment of raf protein kinase-mediated indications |
| GB0814364D0 (en) | 2008-08-05 | 2008-09-10 | Eisai London Res Lab Ltd | Diazaindole derivatives and their use in the inhibition of c-Jun N-terminal kinase |
| JP2012506381A (ja) | 2008-10-21 | 2012-03-15 | 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タンパク質キナーゼ阻害剤 |
| WO2010068483A2 (en) | 2008-11-25 | 2010-06-17 | University Of Rochester | Mlk inhibitors and methods of use |
| EP2373653B1 (en) | 2008-12-05 | 2014-04-02 | F. Hoffmann-La Roche AG | Pyrrolopyrazinyl urea kinase inhibitors |
| ES2921576T3 (es) | 2008-12-19 | 2022-08-29 | Vertex Pharma | Compuestos útiles como inhibidores de la quinasa ATR |
| SG172352A1 (en) | 2008-12-23 | 2011-07-28 | Abbott Lab | Anti-viral compounds |
| BRPI1008020A2 (pt) | 2009-02-11 | 2016-03-15 | Sunovion Pharmaceuticals Inc | antagonistas e agonistas inversos h3 da histamina e métodos de uso dos mesmos |
| JP2012522013A (ja) | 2009-03-27 | 2012-09-20 | ザ ユーエービー リサーチ ファウンデーション | 調節ires媒介翻訳 |
| ES2483594T3 (es) | 2009-07-15 | 2014-08-06 | Abbott Laboratories | Pirrolopirazinas inhibidoras de quinasas |
| US8518945B2 (en) | 2010-03-22 | 2013-08-27 | Hoffmann-La Roche Inc. | Pyrrolopyrazine kinase inhibitors |
| MX2012011549A (es) | 2010-04-08 | 2013-01-29 | Ah Usa 42 Llc | Derivados de 3,5-difenil-isoxazolina sustituida como insecticidas y acaricidas. |
| WO2011130689A1 (en) | 2010-04-15 | 2011-10-20 | Tracon Pharmaceuticals, Inc. | Potentiation of anti-cancer activity through combination therapy with ber pathway inhibitors |
| US8962631B2 (en) | 2010-05-12 | 2015-02-24 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US9334244B2 (en) | 2010-05-12 | 2016-05-10 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| CA2798760A1 (en) | 2010-05-12 | 2011-11-17 | Vertex Pharmaceuticals Incorporated | 2-aminopyridine derivatives useful as inhibitors of atr kinase |
| EP2568984A1 (en) | 2010-05-12 | 2013-03-20 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| NZ603477A (en) | 2010-05-12 | 2014-09-26 | Vertex Pharma | Compounds useful as inhibitors of atr kinase |
| US9062008B2 (en) | 2010-05-12 | 2015-06-23 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| EP2571881A1 (en) | 2010-05-20 | 2013-03-27 | F.Hoffmann-La Roche Ag | Pyrrolopyrazine derivatives as syk and jak inhibitors |
| MX2012013378A (es) | 2010-05-20 | 2013-01-24 | Hoffmann La Roche | Derivados de pirrolo [2, 3-b] pirazina-7-carboxamida y sus uso como inhibidores de cinasa janus (jak) y cinasa tirosina del brazo (syk). |
| MX2013000103A (es) | 2010-06-23 | 2013-06-13 | Vertex Pharma | Derivados de pirrolo-pirazina utiles como inhibidores de cinasa art. |
| CN102311396B (zh) | 2010-07-05 | 2015-01-07 | 暨南大学 | 一种吡嗪类衍生物和其制备方法及在制药中的应用 |
| EP2407478A1 (en) | 2010-07-14 | 2012-01-18 | GENETADI Biotech, S.L. | New cyclotetrapeptides with pro-angiogenic properties |
| MX2013011450A (es) | 2011-04-05 | 2014-02-03 | Vertex Pharma | Compuestos de aminopirazina utiles como inhibidores de la cinasa ataxia telangiectasia mutada y rad3 relacionados (atr). |
| CN103502249A (zh) | 2011-05-17 | 2014-01-08 | 普林斯匹亚生物制药公司 | 作为酪氨酸激酶抑制剂的氮杂吲哚衍生物 |
| US9309250B2 (en) | 2011-06-22 | 2016-04-12 | Vertex Pharmaceuticals Incorporated | Substituted pyrrolo[2,3-b]pyrazines as ATR kinase inhibitors |
| US8822469B2 (en) | 2011-06-22 | 2014-09-02 | Vertex Pharmaceuticals Incorporated | Pyrrolo[2,3-B]pyrazines useful as inhibitors of ATR kinase |
| EP2723747A1 (en) | 2011-06-22 | 2014-04-30 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of atr kinase |
| CN108685922A (zh) | 2011-09-30 | 2018-10-23 | 沃泰克斯药物股份有限公司 | 用atr抑制剂治疗胰腺癌和非小细胞肺癌 |
| CN106496173A (zh) | 2011-09-30 | 2017-03-15 | 沃泰克斯药物股份有限公司 | 用于制备可用作atr激酶抑制剂的化合物的方法 |
| WO2013049720A1 (en) | 2011-09-30 | 2013-04-04 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| US8765751B2 (en) | 2011-09-30 | 2014-07-01 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| WO2013049722A1 (en) | 2011-09-30 | 2013-04-04 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| US8846918B2 (en) | 2011-11-09 | 2014-09-30 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| JP2015502925A (ja) | 2011-11-09 | 2015-01-29 | 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ピラジン化合物 |
| US8841450B2 (en) | 2011-11-09 | 2014-09-23 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US8841337B2 (en) | 2011-11-09 | 2014-09-23 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US8846917B2 (en) | 2011-11-09 | 2014-09-30 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
-
2011
- 2011-05-12 US US13/106,173 patent/US8962631B2/en not_active Expired - Fee Related
- 2011-05-12 EP EP11731560A patent/EP2569289A1/en not_active Withdrawn
- 2011-05-12 JP JP2013510296A patent/JP2013526539A/ja active Pending
- 2011-05-12 WO PCT/US2011/036239 patent/WO2011143419A1/en not_active Ceased
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003516974A (ja) * | 1999-12-17 | 2003-05-20 | カイロン コーポレイション | グリコーゲンシンターゼキナーゼ3のピラジンベースインヒビター |
| JP2006520794A (ja) * | 2003-03-21 | 2006-09-14 | スミスクライン ビーチャム コーポレーション | 化合物 |
| JP2006521357A (ja) * | 2003-03-24 | 2006-09-21 | メルク エンド カムパニー インコーポレーテッド | ナトリウムチャンネル遮断薬としてのビアリール置換6員複素環化合物 |
| JP2007524682A (ja) * | 2004-02-12 | 2007-08-30 | メルク エンド カムパニー インコーポレーテッド | 代謝調節型グルタミン酸受容体−5の調節物質としてのビピリジルアミド |
| WO2006124874A2 (en) * | 2005-05-12 | 2006-11-23 | Kalypsys, Inc. | Inhibitors of b-raf kinase |
| JP2009541247A (ja) * | 2006-06-19 | 2009-11-26 | エフ.ホフマン−ラ ロシュ アーゲー | 2−ピラジンカルボキシアミド誘導体 |
| WO2008156174A1 (ja) * | 2007-06-21 | 2008-12-24 | Taisho Pharmaceutical Co., Ltd. | ピラジンアミド化合物 |
| WO2009037247A1 (en) * | 2007-09-17 | 2009-03-26 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
| JP2012508260A (ja) * | 2008-11-10 | 2012-04-05 | 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キナーゼの阻害剤として有用な化合物 |
| JP2014518545A (ja) * | 2011-03-04 | 2014-07-31 | ローカス ファーマシューティカルズ インコーポレイテッド | アミノピラジン化合物 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020217733A1 (ja) * | 2019-04-26 | 2020-10-29 | 株式会社カネカ | Vadadustat中間体の製造方法 |
| JPWO2020217733A1 (enExample) * | 2019-04-26 | 2020-10-29 | ||
| JP7470106B2 (ja) | 2019-04-26 | 2024-04-17 | 株式会社カネカ | Vadadustat中間体の製造方法 |
| US12134600B2 (en) | 2019-04-26 | 2024-11-05 | Kaneka Corporation | Method for producing a vadadustat intermediate |
Also Published As
| Publication number | Publication date |
|---|---|
| US20120035407A1 (en) | 2012-02-09 |
| WO2011143419A1 (en) | 2011-11-17 |
| EP2569289A1 (en) | 2013-03-20 |
| US8962631B2 (en) | 2015-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8962631B2 (en) | Compounds useful as inhibitors of ATR kinase | |
| JP5856151B2 (ja) | Atrキナーゼ阻害剤として有用な2−アミノピリジン誘導体 | |
| US9334244B2 (en) | Compounds useful as inhibitors of ATR kinase | |
| US9062008B2 (en) | Compounds useful as inhibitors of ATR kinase | |
| US8623869B2 (en) | Compounds useful as inhibitors of ATR kinase | |
| US8969356B2 (en) | Compounds useful as inhibitors of ATR kinase | |
| EP2152696B1 (en) | Aminopyrimidines useful as kinase inhibitors | |
| JP2010528021A (ja) | キナーゼのインヒビターとして有用なチアゾールおよびピラゾール | |
| JP2013231083A (ja) | キナーゼ阻害剤として有用なチアゾールおよびピラゾール | |
| US20140037754A1 (en) | Aminopyrimidines useful as kinase inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140509 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140509 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150223 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150226 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150525 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20151112 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20160427 |