WO2008133155A1 - 二環式ヘテロ環化合物 - Google Patents

二環式ヘテロ環化合物 Download PDF

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Publication number
WO2008133155A1
WO2008133155A1 PCT/JP2008/057465 JP2008057465W WO2008133155A1 WO 2008133155 A1 WO2008133155 A1 WO 2008133155A1 JP 2008057465 W JP2008057465 W JP 2008057465W WO 2008133155 A1 WO2008133155 A1 WO 2008133155A1
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WO
WIPO (PCT)
Prior art keywords
platelet aggregation
inhibiting activity
bicyclic heterocyclic
heterocyclic compound
compound
Prior art date
Application number
PCT/JP2008/057465
Other languages
English (en)
French (fr)
Inventor
Yuji Koga
Takao Okuda
Takashi Kamikubo
Michihito Kageyama
Hiroyuki Moritomo
Original Assignee
Astellas Pharma Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Astellas Pharma Inc. filed Critical Astellas Pharma Inc.
Priority to JP2009511835A priority Critical patent/JPWO2008133155A1/ja
Priority to US12/596,643 priority patent/US20100113391A1/en
Priority to EP08740535A priority patent/EP2138482A4/en
Publication of WO2008133155A1 publication Critical patent/WO2008133155A1/ja

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D217/00Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 nitrogen-containing ring
    • C07D217/24Oxygen atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/04Antineoplastic agents specific for metastasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72Quinazolines; Hydrogenated quinazolines
    • C07D239/95Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C07D239/96Two oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D243/00Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/141,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/06Heterocyclic 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 linked by a carbon chain containing only aliphatic carbon atoms

Abstract

【課題】P2Y12阻害作用を有する医薬、特に血小板凝集阻害剤として有用な化合物を提供する。 【解決手段】発明者等は、P2Y12阻害剤について鋭意検討した結果、低級アルキル、シクロアルキル又は低級アルキレン-シクロアルキルで置換されたアミノ基を特定の位置に有することを特徴とするキナゾリンジオン、イソキノロン等の二環式ヘテロ環化合物が、優れた血小板凝集阻害作用を有することを見出し本発明を完成した。本発明化合物は、優れたP2Y12阻害作用及び血小板凝集阻害作用を有することから、血小板凝集阻害剤として有用である。
PCT/JP2008/057465 2007-04-19 2008-04-17 二環式ヘテロ環化合物 WO2008133155A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2009511835A JPWO2008133155A1 (ja) 2007-04-19 2008-04-17 二環式ヘテロ環化合物
US12/596,643 US20100113391A1 (en) 2007-04-19 2008-04-17 Bicyclic heterocyclic compound
EP08740535A EP2138482A4 (en) 2007-04-19 2008-04-17 BICYCLIC HETEROCYCLIC COMPOUND

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007109958 2007-04-19
JP2007-109958 2007-04-19

Publications (1)

Publication Number Publication Date
WO2008133155A1 true WO2008133155A1 (ja) 2008-11-06

Family

ID=39925611

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/057465 WO2008133155A1 (ja) 2007-04-19 2008-04-17 二環式ヘテロ環化合物

Country Status (5)

Country Link
US (1) US20100113391A1 (ja)
EP (1) EP2138482A4 (ja)
JP (1) JPWO2008133155A1 (ja)
TW (1) TW200911755A (ja)
WO (1) WO2008133155A1 (ja)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2944282A1 (fr) * 2009-04-09 2010-10-15 Sanofi Aventis Derives de quinazolinedione, leur preparation et leurs diverses applications therapeutiques
WO2011024933A1 (ja) 2009-08-28 2011-03-03 第一三共株式会社 3-(ビアリールオキシ)プロピオン酸誘導体
US8846654B2 (en) 2009-04-09 2014-09-30 Sanofi Therapeutic applications in the cardiovascular field of quinazolinedione derivatives

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8107260B2 (en) * 2007-11-15 2012-01-31 Illinois Tool Works Inc. EMI shielding and environmental seal device
WO2012174013A2 (en) * 2011-06-14 2012-12-20 Cardeus Pharmaceuticals, Inc. Treatment of cardiovascular disease, stroke, and inflammatory conditions
WO2013033178A1 (en) 2011-08-30 2013-03-07 University Of Utah Research Foundation Methods and compositions for treating nephrogenic diabetes insipidus
WO2016071792A1 (en) * 2014-11-03 2016-05-12 Laboratorio Chimico Internazionale S.P.A. Method for the preparation of 1-(2-halogen-ethyl)-4 piperidine-carboxylic acid ethyl esters
US11884645B2 (en) 2018-03-02 2024-01-30 Inflazome Limited Sulfonyl acetamides as NLRP3 inhibitors
US11530200B2 (en) 2018-03-02 2022-12-20 Inflazome Limited Compounds
US20200407340A1 (en) * 2018-03-02 2020-12-31 Inflazome Limited Sulfonamide derivates as nlrp3 inhibitors
US11834433B2 (en) 2018-03-02 2023-12-05 Inflazome Limited Compounds

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63316778A (ja) * 1987-06-01 1988-12-26 アメリカン・サイアナミド・カンパニ− 3−ヘテロアルキル−2,4−キナゾリンジオン、3−ヘテロアリ−ル−1,2,3−ベンゾトリアジン−4(3h)−オン、3−ヘテロアリ−ルアルキル−4−キナゾリノン
JPH03181469A (ja) 1989-12-11 1991-08-07 Kyorin Pharmaceut Co Ltd キナゾリン―3―アルカン酸誘導体とその塩およびその製造法
WO1994029273A1 (en) * 1993-06-09 1994-12-22 Smithkline Beecham Corporation Bicyclic fibrinogen antagonists
WO2002036631A1 (fr) 2000-11-01 2002-05-10 Yamanouchi Pharmaceutical Co., Ltd. Procede de criblage d'anti-plaquettes
WO2003011872A1 (en) 2001-08-02 2003-02-13 Millennium Pharmaceuticals, Inc. Platelet adp receptor inhibitors
WO2004060878A2 (en) 2002-12-31 2004-07-22 Vertex Pharmaceuticals Incorporated Inhibitors of phosphatases
WO2005009971A1 (ja) 2003-07-24 2005-02-03 Astellas Pharma Inc. キノロン誘導体又はその塩
WO2005032488A2 (en) 2003-10-03 2005-04-14 Portola Pharmaceuticals, Inc. 2,4-dioxo-3-quinazolinylaryl sulfonylureas
WO2005035520A1 (en) 2003-10-03 2005-04-21 Portola Pharmaceuticals, Inc. Substituted isoquinolinones
WO2005061466A1 (ja) 2003-12-22 2005-07-07 Ajinomoto Co., Inc. 新規フェニルアラニン誘導体
WO2006077851A1 (ja) 2005-01-20 2006-07-27 Astellas Pharma Inc. キノロン誘導体又はその塩
WO2007028789A1 (en) 2005-09-07 2007-03-15 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Quinazoline derivatives as antiviral agents
WO2007056219A2 (en) 2005-11-03 2007-05-18 Portola Pharmaceuticals, Inc. [4-(6-halo-7-substituted-2,4-dioxo-1,4-dihydro-2h-quinazolin-3-yl)-phenyl]-5-chloro-thiophen-2-yl-sulfonylureas and forms and methods related thereto
WO2007105751A1 (ja) 2006-03-16 2007-09-20 Astellas Pharma Inc. キノロン誘導体又はその製薬学的に許容される塩

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63316778A (ja) * 1987-06-01 1988-12-26 アメリカン・サイアナミド・カンパニ− 3−ヘテロアルキル−2,4−キナゾリンジオン、3−ヘテロアリ−ル−1,2,3−ベンゾトリアジン−4(3h)−オン、3−ヘテロアリ−ルアルキル−4−キナゾリノン
JPH03181469A (ja) 1989-12-11 1991-08-07 Kyorin Pharmaceut Co Ltd キナゾリン―3―アルカン酸誘導体とその塩およびその製造法
WO1994029273A1 (en) * 1993-06-09 1994-12-22 Smithkline Beecham Corporation Bicyclic fibrinogen antagonists
WO2002036631A1 (fr) 2000-11-01 2002-05-10 Yamanouchi Pharmaceutical Co., Ltd. Procede de criblage d'anti-plaquettes
WO2003011872A1 (en) 2001-08-02 2003-02-13 Millennium Pharmaceuticals, Inc. Platelet adp receptor inhibitors
WO2004060878A2 (en) 2002-12-31 2004-07-22 Vertex Pharmaceuticals Incorporated Inhibitors of phosphatases
WO2005009971A1 (ja) 2003-07-24 2005-02-03 Astellas Pharma Inc. キノロン誘導体又はその塩
WO2005032488A2 (en) 2003-10-03 2005-04-14 Portola Pharmaceuticals, Inc. 2,4-dioxo-3-quinazolinylaryl sulfonylureas
WO2005035520A1 (en) 2003-10-03 2005-04-21 Portola Pharmaceuticals, Inc. Substituted isoquinolinones
WO2005061466A1 (ja) 2003-12-22 2005-07-07 Ajinomoto Co., Inc. 新規フェニルアラニン誘導体
WO2006077851A1 (ja) 2005-01-20 2006-07-27 Astellas Pharma Inc. キノロン誘導体又はその塩
WO2007028789A1 (en) 2005-09-07 2007-03-15 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Quinazoline derivatives as antiviral agents
WO2007056219A2 (en) 2005-11-03 2007-05-18 Portola Pharmaceuticals, Inc. [4-(6-halo-7-substituted-2,4-dioxo-1,4-dihydro-2h-quinazolin-3-yl)-phenyl]-5-chloro-thiophen-2-yl-sulfonylureas and forms and methods related thereto
WO2007105751A1 (ja) 2006-03-16 2007-09-20 Astellas Pharma Inc. キノロン誘導体又はその製薬学的に許容される塩

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
"Drug Design", vol. 7, 1990, HIROGAWA PUBLISHING COMPANY, article "Pharmaceutical Research and Development", pages: 163 - 198
GREENE; WUTS: "Protective Groups in Organic Synthesis", 1999
JOURNAL OF THE AMERICAN COLLEGE OF CARDIOLOGY, vol. 12, 1988, pages 616 - 623
MOL. PHARMACOL., vol. 60, 2001, pages 432
NUCLEIC ACID RES., vol. 18, 1990, pages 5322
PROG. MED., vol. 5, 1985, pages 2157 - 2161
See also references of EP2138482A4 *
THE CLINICS, vol. 52, 2003, pages 1516 - 1521

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2944282A1 (fr) * 2009-04-09 2010-10-15 Sanofi Aventis Derives de quinazolinedione, leur preparation et leurs diverses applications therapeutiques
WO2010116088A3 (fr) * 2009-04-09 2010-12-16 Sanofi-Aventis Dérivés de quinazolinedione, leur préparation et leurs diverses applications thérapeutiques
CN102459244A (zh) * 2009-04-09 2012-05-16 赛诺菲 喹唑啉二酮衍生物、其制备及其多种治疗用途
JP2012523397A (ja) * 2009-04-09 2012-10-04 サノフイ キナゾリンジオン誘導体、その調製およびその様々な治療上の使用
US8722659B2 (en) 2009-04-09 2014-05-13 Sanofi Quinazolinedione derivatives, preparation thereof and various therapeutic uses thereof
US8846654B2 (en) 2009-04-09 2014-09-30 Sanofi Therapeutic applications in the cardiovascular field of quinazolinedione derivatives
CN102459244B (zh) * 2009-04-09 2015-07-08 赛诺菲 喹唑啉二酮衍生物、其制备及其多种治疗用途
EA021765B1 (ru) * 2009-04-09 2015-08-31 Санофи Производные хиназолиндиона, их получение и их различные терапевтические применения
WO2011024933A1 (ja) 2009-08-28 2011-03-03 第一三共株式会社 3-(ビアリールオキシ)プロピオン酸誘導体
US8729095B2 (en) 2009-08-28 2014-05-20 Daiichi Sankyo Company, Limited 3-(biaryloxy)propionic acid derivatives for prevention and/or treatment of thromboembolic diseases

Also Published As

Publication number Publication date
EP2138482A1 (en) 2009-12-30
JPWO2008133155A1 (ja) 2010-07-22
US20100113391A1 (en) 2010-05-06
TW200911755A (en) 2009-03-16
EP2138482A4 (en) 2011-06-15

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