JP2014521750A - マクロラクタムを調製するための方法および中間体 - Google Patents

マクロラクタムを調製するための方法および中間体 Download PDF

Info

Publication number
JP2014521750A
JP2014521750A JP2014526217A JP2014526217A JP2014521750A JP 2014521750 A JP2014521750 A JP 2014521750A JP 2014526217 A JP2014526217 A JP 2014526217A JP 2014526217 A JP2014526217 A JP 2014526217A JP 2014521750 A JP2014521750 A JP 2014521750A
Authority
JP
Japan
Prior art keywords
compound
salt
compounds
salts
added
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
Application number
JP2014526217A
Other languages
English (en)
Japanese (ja)
Inventor
シユイ,フオン
ハンフリー,ガイ
ペイ,タオ
ソン,ジーグオ・ジエイク
ワン,タオ
アルテイノ,ローラ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Sharp and Dohme LLC
Original Assignee
Merck Sharp and Dohme LLC
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 Merck Sharp and Dohme LLC filed Critical Merck Sharp and Dohme LLC
Publication of JP2014521750A publication Critical patent/JP2014521750A/ja
Pending legal-status Critical Current

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/04Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/32Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/34Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/14Preparation of carboxylic acid esters from carboxylic acid halides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/013Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12Acetic acid esters
    • 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
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/16Peri-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08Tripeptides
    • C07K5/0802Tripeptides with the first amino acid being neutral
    • C07K5/0804Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/12Cyclic peptides with only normal peptide bonds in the ring
    • C07K5/126Tetrapeptides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides

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)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Communicable Diseases (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Veterinary Medicine (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Cephalosporin Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
JP2014526217A 2011-08-19 2012-08-16 マクロラクタムを調製するための方法および中間体 Pending JP2014521750A (ja)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US201161525462P 2011-08-19 2011-08-19
US61/525,462 2011-08-19
US201161533439P 2011-09-12 2011-09-12
US61/533,439 2011-09-12
US201161533915P 2011-09-13 2011-09-13
US61/533,915 2011-09-13
US201161539540P 2011-09-27 2011-09-27
US61/539,540 2011-09-27
PCT/US2012/051177 WO2013028470A1 (en) 2011-08-19 2012-08-16 Process and intermediates for preparing macrolactams

Publications (1)

Publication Number Publication Date
JP2014521750A true JP2014521750A (ja) 2014-08-28

Family

ID=47746773

Family Applications (2)

Application Number Title Priority Date Filing Date
JP2014526217A Pending JP2014521750A (ja) 2011-08-19 2012-08-16 マクロラクタムを調製するための方法および中間体
JP2014526215A Pending JP2014524442A (ja) 2011-08-19 2012-08-16 Hcvプロテアーゼ阻害剤の結晶形態

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP2014526215A Pending JP2014524442A (ja) 2011-08-19 2012-08-16 Hcvプロテアーゼ阻害剤の結晶形態

Country Status (11)

Country Link
US (3) US9238604B2 (enExample)
EP (3) EP2744331A4 (enExample)
JP (2) JP2014521750A (enExample)
KR (2) KR20140053330A (enExample)
CN (2) CN103874414A (enExample)
AU (2) AU2012299218A1 (enExample)
BR (2) BR112014003802A2 (enExample)
CA (2) CA2844388A1 (enExample)
MX (2) MX2014001945A (enExample)
RU (2) RU2014110399A (enExample)
WO (3) WO2013028470A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018524382A (ja) * 2015-07-21 2018-08-30 ティーピー・セラピューティクス・インコーポレイテッドTp Therapeutics,Inc. キラルジアリール大環状分子及びその使用

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011014487A1 (en) 2009-07-30 2011-02-03 Merck Sharp & Dohme Corp. Hepatitis c virus ns3 protease inhibitors
US8957203B2 (en) 2011-05-05 2015-02-17 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
EP2744331A4 (en) 2011-08-19 2015-01-21 Merck Sharp & Dohme METHOD AND INTERMEDIATE PRODUCTS FOR THE MANUFACTURE OF MACROLACTAMEN
UA119315C2 (uk) 2012-07-03 2019-06-10 Гіліад Фармассет Елелсі Інгібітори вірусу гепатиту с
BR112015007879A2 (pt) 2012-10-19 2017-07-04 Bristol Myers Squibb Co inibidores do vírus da hepatite c
WO2014070964A1 (en) 2012-11-02 2014-05-08 Bristol-Myers Squibb Company Hepatitis c virus inhibitors
US9334279B2 (en) 2012-11-02 2016-05-10 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US9643999B2 (en) 2012-11-02 2017-05-09 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
WO2014070974A1 (en) 2012-11-05 2014-05-08 Bristol-Myers Squibb Company Hepatitis c virus inhibitors
EP2764866A1 (en) 2013-02-07 2014-08-13 IP Gesellschaft für Management mbH Inhibitors of nedd8-activating enzyme
US9580463B2 (en) 2013-03-07 2017-02-28 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
MX2015013224A (es) 2013-03-15 2015-12-11 Gilead Sciences Inc Inhibidores macrociclicos y biciclicos del virus de la hepatitis c.
US9873707B2 (en) 2013-10-18 2018-01-23 Merck Sharp & Dohme Corp. Methods and intermediates for preparing macrolactams
WO2015095437A1 (en) * 2013-12-20 2015-06-25 Merck Sharp & Dohme Corp. Methods and intermediates for the preparation of macrolactams
DK3636649T3 (da) * 2014-01-24 2024-05-21 Turning Point Therapeutics Inc Diarylmakrocykler som modulatorer af proteinkinaser
AU2015269306B2 (en) * 2014-06-06 2020-06-25 Abbvie Inc. Crystal forms
EP3317285B1 (en) 2015-07-02 2021-01-27 Turning Point Therapeutics, Inc. Chiral diaryl macrocycles as modulators of protein kinases
WO2017007759A1 (en) * 2015-07-06 2017-01-12 Tp Therapeutics, Inc. Diaryl macrocycle polymorph
EP3454856B1 (en) 2016-05-10 2024-09-11 C4 Therapeutics, Inc. Heterocyclic degronimers for target protein degradation
CN109641874A (zh) 2016-05-10 2019-04-16 C4医药公司 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体
ES2990061T3 (es) 2016-05-10 2024-11-28 C4 Therapeutics Inc Degronímeros espirocíclicos para la degradación de proteínas diana
WO2017197051A1 (en) 2016-05-10 2017-11-16 C4 Therapeutics, Inc. Amine-linked c3-glutarimide degronimers for target protein degradation
US10689400B2 (en) 2016-07-28 2020-06-23 Turning Point Therapeutics, Inc. Macrocycle kinase inhibitors
TWI808958B (zh) 2017-01-25 2023-07-21 美商特普醫葯公司 涉及二芳基巨環化合物之組合療法
EP3641762A4 (en) 2017-06-20 2021-03-10 C4 Therapeutics, Inc. N / O-LINKED DEGRONES AND DEGRONIMERS FOR PROTEIN DEGRADATION
JP7224334B2 (ja) 2017-07-28 2023-02-17 ターニング・ポイント・セラピューティクス・インコーポレイテッド 大環式化合物およびその使用
PT3728271T (pt) 2017-12-19 2022-10-06 Turning Point Therapeutics Inc Compostos macrocíclicos para tratar doenças
CN111057045A (zh) * 2019-12-18 2020-04-24 安徽红杉生物医药科技有限公司 Hcv ns3/4a蛋白酶抑制剂中间体及其合成方法、应用
CN112174982A (zh) * 2020-09-10 2021-01-05 上海希迈医药科技有限公司 一种洛普替尼晶型及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010011566A1 (en) * 2008-07-22 2010-01-28 Merck & Co., Inc. Macrocyclic quinoxaline compounds as hcv ns3 protease inhibitors

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4871868A (en) 1987-03-11 1989-10-03 Takeda Chemical Industries, Ltd. Production of substituted acetylenic compounds
GB9207987D0 (en) 1992-04-10 1992-05-27 Smithkline Beecham Plc Novel container and closure
US5716960A (en) * 1995-01-13 1998-02-10 U.S. Bioscience Inc. And Individuals Crystalline trimetrexate salts and the process for making the same
ZA98879B (en) * 1997-02-04 1998-08-03 Ono Pharmaceutical Co Omega-cycloalkyl-prostaglandin e2 derivatives
NO317155B1 (no) 1997-02-04 2004-08-30 Ono Pharmaceutical Co <omega>-cykloalkyl-prostagladin-E<N>2</N>-derivater
KR20130076903A (ko) * 2005-02-18 2013-07-08 미쓰비시 타나베 파마 코퍼레이션 프롤린 유도체의 염 또는 그 용매화물 및 그 제조 방법
US7834145B2 (en) 2005-03-22 2010-11-16 Merck Sharp & Dohme Corp. HCV protease substrates
AU2006242475B2 (en) 2005-05-02 2011-07-07 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
AR057456A1 (es) 2005-07-20 2007-12-05 Merck & Co Inc Inhibidores de la proteasa ns3 del vhc
CN101228181B (zh) * 2005-07-20 2013-09-18 默沙东公司 Hcv ns3蛋白酶抑制剂
US8278322B2 (en) 2005-08-01 2012-10-02 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
MX2008011079A (es) 2006-03-07 2008-09-05 Procter & Gamble Composiciones para teñir oxidativamente fibras de queratina y metodos p ara utilizar tales composiciones.
GB0609492D0 (en) 2006-05-15 2006-06-21 Angeletti P Ist Richerche Bio Therapeutic agents
GB0612423D0 (en) 2006-06-23 2006-08-02 Angeletti P Ist Richerche Bio Therapeutic agents
US8309540B2 (en) 2006-10-24 2012-11-13 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
WO2008051477A2 (en) 2006-10-24 2008-05-02 Merck & Co., Inc. Hcv ns3 protease inhibitors
US8377874B2 (en) 2006-10-27 2013-02-19 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
JP5268927B2 (ja) 2006-10-27 2013-08-21 メルク・シャープ・アンド・ドーム・コーポレーション Hcvns3プロテアーゼ阻害剤
BRPI0811020A2 (pt) 2007-05-03 2015-07-21 Intermune Inc Composto, composição farmacêutica e métodos de inibição da atividade da protease ns3/ns4, de tratamento da fibrose hepática, de intensificação da função hepática em indivíduo com infecção do vírus da hepatite c e métodos de síntese de compostos, de administração de inibidor da infecção do vírus da hepatite c (hcv) e de distribuição de forma de dosagem oral.
US8927569B2 (en) 2007-07-19 2015-01-06 Merck Sharp & Dohme Corp. Macrocyclic compounds as antiviral agents
CA2714604A1 (en) 2008-02-25 2009-09-03 Merck Sharp & Dohme Corp. Macrocyclic hcv ns3 protease inhibitors
WO2009131196A1 (ja) * 2008-04-24 2009-10-29 武田薬品工業株式会社 置換ピロリジン誘導体およびその用途
JP2011518836A (ja) * 2008-04-24 2011-06-30 インサイト・コーポレイション 大環状化合物およびそれらのキナーゼ阻害剤としての使用
JP2011518882A (ja) 2008-04-28 2011-06-30 メルク・シャープ・エンド・ドーム・コーポレイション Hcvns3プロテアーゼ阻害剤
WO2011014487A1 (en) 2009-07-30 2011-02-03 Merck Sharp & Dohme Corp. Hepatitis c virus ns3 protease inhibitors
EP2470189A4 (en) * 2009-08-27 2013-01-23 Merck Sharp & Dohme METHOD FOR PRODUCING PROTEASE INHIBITORS OF HEPATITIS C VIRUS
EP2744331A4 (en) 2011-08-19 2015-01-21 Merck Sharp & Dohme METHOD AND INTERMEDIATE PRODUCTS FOR THE MANUFACTURE OF MACROLACTAMEN

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010011566A1 (en) * 2008-07-22 2010-01-28 Merck & Co., Inc. Macrocyclic quinoxaline compounds as hcv ns3 protease inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JPN6016014786; Song, Zhiguo J.; Tellers, David M.; Journet, Michel; Kuethe, Jeffrey T.; Lieberman, David; Humphrey,: 'Synthesis of vaniprevir (MK-7009): Lactamization to prepare a 22-membered macrocycle' Journal of Organic Chemistry 76(19), 2011, 7804-7815 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018524382A (ja) * 2015-07-21 2018-08-30 ティーピー・セラピューティクス・インコーポレイテッドTp Therapeutics,Inc. キラルジアリール大環状分子及びその使用
US11452725B2 (en) 2015-07-21 2022-09-27 Turning Point Therapeutics, Inc. Chiral diaryl macrocycles and uses thereof

Also Published As

Publication number Publication date
EP2744331A1 (en) 2014-06-25
KR20140053330A (ko) 2014-05-07
AU2012299223A1 (en) 2014-02-27
CA2844386A1 (en) 2013-02-28
CN103889439A (zh) 2014-06-25
KR20140059236A (ko) 2014-05-15
EP2744507A1 (en) 2014-06-25
EP2744336A1 (en) 2014-06-25
US9242917B2 (en) 2016-01-26
CA2844388A1 (en) 2013-02-28
US9238604B2 (en) 2016-01-19
EP2744336A4 (en) 2014-12-31
JP2014524442A (ja) 2014-09-22
US9073825B2 (en) 2015-07-07
CN103874414A (zh) 2014-06-18
RU2014110400A (ru) 2015-09-27
BR112014003802A2 (pt) 2017-06-13
WO2013028471A1 (en) 2013-02-28
WO2013028470A1 (en) 2013-02-28
US20140243519A1 (en) 2014-08-28
BR112014003798A2 (pt) 2017-03-01
US20140200343A1 (en) 2014-07-17
US20140206605A1 (en) 2014-07-24
EP2744336B1 (en) 2017-07-05
EP2744507A4 (en) 2015-01-28
EP2744331A4 (en) 2015-01-21
MX2014001944A (es) 2014-03-27
AU2012299218A1 (en) 2014-02-20
MX2014001945A (es) 2014-03-27
RU2014110399A (ru) 2015-09-27
WO2013028465A1 (en) 2013-02-28

Similar Documents

Publication Publication Date Title
JP2014521750A (ja) マクロラクタムを調製するための方法および中間体
JP6034802B2 (ja) 大環状ラクタムの調製のための方法および中間体
CA2486308C (en) Hepatitis c virus inhibitors
ES2470568T3 (es) Inhibidores macroc�clicos del virus de la hepatitis C
JP5789260B2 (ja) C型肝炎ウイルスのプロテアーゼ阻害薬の調製方法
KR102090780B1 (ko) 혈전색전성 질환의 치료를 위한 인자 xia 억제제로서 치환된 피롤리딘
JP2008517896A (ja) C型肝炎ウイルスプロテアーゼの阻害剤並びにそれを用いた組成物及び治療
KR20250002239A (ko) 치환된 스피로옥스인돌 유도체의 제조 방법
CN103387601B (zh) 抗登革热病毒(denv)杂环肽类化合物及其制备方法和用途
US9873707B2 (en) Methods and intermediates for preparing macrolactams
WO2015095430A1 (en) Methods and intermediates for the preparation of macrolactams
HK1136824B (en) Macrocyclic inhibitors of hepatitis c virus

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20150812

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20160303

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20160426

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20160720

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20170110