KR101434841B1 - 2-치환-8-알킬-7-옥소-7,8-디하이드로피리도[2,3-d] 피리미딘-6-카르보니트릴 및 이의 용도 - Google Patents

2-치환-8-알킬-7-옥소-7,8-디하이드로피리도[2,3-d] 피리미딘-6-카르보니트릴 및 이의 용도 Download PDF

Info

Publication number
KR101434841B1
KR101434841B1 KR1020137004979A KR20137004979A KR101434841B1 KR 101434841 B1 KR101434841 B1 KR 101434841B1 KR 1020137004979 A KR1020137004979 A KR 1020137004979A KR 20137004979 A KR20137004979 A KR 20137004979A KR 101434841 B1 KR101434841 B1 KR 101434841B1
Authority
KR
South Korea
Prior art keywords
compound
cancer
formula
oxo
amino
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.)
Active
Application number
KR1020137004979A
Other languages
English (en)
Korean (ko)
Other versions
KR20130098314A (ko
Inventor
이. 프렘쿠마르 레디
엠.브이. 라마나 레디
Original Assignee
템플 유니버시티-오브 더 커먼웰쓰 시스템 오브 하이어 에듀케이션
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 템플 유니버시티-오브 더 커먼웰쓰 시스템 오브 하이어 에듀케이션 filed Critical 템플 유니버시티-오브 더 커먼웰쓰 시스템 오브 하이어 에듀케이션
Publication of KR20130098314A publication Critical patent/KR20130098314A/ko
Application granted granted Critical
Publication of KR101434841B1 publication Critical patent/KR101434841B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/08Drugs for disorders of the urinary system of the prostate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/08Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • 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
    • A61P9/00Drugs for disorders of the cardiovascular system
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Vascular Medicine (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Oncology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
KR1020137004979A 2010-08-05 2011-07-21 2-치환-8-알킬-7-옥소-7,8-디하이드로피리도[2,3-d] 피리미딘-6-카르보니트릴 및 이의 용도 Active KR101434841B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US37094610P 2010-08-05 2010-08-05
US61/370,946 2010-08-05
PCT/US2011/044807 WO2012018540A1 (en) 2010-08-05 2011-07-21 2-substituted-8-alkyl-7-oxo-7,8-dihydropyrido[2,3-d] pyrimidine-6-carbonitriles and uses thereof

Publications (2)

Publication Number Publication Date
KR20130098314A KR20130098314A (ko) 2013-09-04
KR101434841B1 true KR101434841B1 (ko) 2014-08-29

Family

ID=45559737

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020137004979A Active KR101434841B1 (ko) 2010-08-05 2011-07-21 2-치환-8-알킬-7-옥소-7,8-디하이드로피리도[2,3-d] 피리미딘-6-카르보니트릴 및 이의 용도

Country Status (17)

Country Link
US (1) US8987267B2 (enExample)
EP (1) EP2600719B1 (enExample)
JP (1) JP5512894B2 (enExample)
KR (1) KR101434841B1 (enExample)
CN (1) CN103200822B (enExample)
AU (1) AU2011286282B2 (enExample)
BR (1) BR112013002375B1 (enExample)
CA (1) CA2807498C (enExample)
DK (1) DK2600719T3 (enExample)
EA (1) EA022527B1 (enExample)
ES (1) ES2525866T3 (enExample)
IL (1) IL224555A (enExample)
MX (1) MX2013001427A (enExample)
NZ (1) NZ606281A (enExample)
PL (1) PL2600719T3 (enExample)
PT (1) PT2600719E (enExample)
WO (1) WO2012018540A1 (enExample)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112013002375B1 (pt) * 2010-08-05 2020-05-12 Temple University - Of The Commonwealth System Of Higher Education Composto, processo de preparação do mesmo, composição farmacêutica, e, usos de um composto
WO2014031571A1 (en) * 2012-08-21 2014-02-27 Icahn School Of Medicine At Mount Sinai Treatment of viral infections
EP3733184B1 (en) 2013-03-14 2023-08-30 Icahn School of Medicine at Mount Sinai Pyrimidine compounds for use in the treatment of cancer
WO2015154064A2 (en) 2014-04-04 2015-10-08 Del Mar Pharmaceuticals Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer
AU2015296322B2 (en) 2014-07-26 2019-09-19 Sunshine Lake Pharma Co., Ltd. 2-amino-pyrido[2,3-d]pyrimidin-7(8h)-one derivatives as CDK inhibitors and uses thereof
CN104447739B (zh) * 2014-11-07 2016-02-17 郑州泰基鸿诺药物科技有限公司 一种氘代Palbociclib衍生物、制备方法及应用
CN104496983B (zh) 2014-11-26 2016-06-08 苏州明锐医药科技有限公司 一种帕博西尼的制备方法
CN104447743B (zh) * 2014-11-26 2016-03-02 苏州明锐医药科技有限公司 帕博西尼的制备方法
CN104478874B (zh) * 2014-12-08 2016-03-02 新发药业有限公司 一种帕博赛布的制备方法
CN104610254B (zh) * 2015-01-26 2017-02-01 新发药业有限公司 一种帕博赛布的低成本制备方法
CN105111205B (zh) * 2015-09-12 2017-01-04 山东罗欣药业集团股份有限公司 一种帕博西尼的制备方法
JP7044801B2 (ja) 2016-12-16 2022-03-30 シーストーン・ファーマスーティカルズ・(スージョウ)・カンパニー・リミテッド Cdk4/6阻害剤
BR112020015431A2 (pt) 2018-02-15 2020-12-08 Nuvation Bio Inc. Compostos heterocíclicos como inibidores de quinase
KR102286701B1 (ko) * 2018-09-28 2021-08-06 재단법인 대구경북첨단의료산업진흥재단 피리도[2,3-d]피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 포함하는 암의 예방 또는 치료용 약학적 조성물
US20220002293A1 (en) * 2018-11-12 2022-01-06 Onconova Therapeutics, Inc. 8-cyclopentyl-7-oxo-2-(4-piperazin-1-yl-phenylamino)-7, 8-dihydro-pyrido [2,3-d]pyrimidine-6-carbonitrile and uses thereof in treating proliferative disorders
TWI818930B (zh) * 2018-11-12 2023-10-21 美商昂可諾法治療股份有限公司 8-環戊基-7-側氧基-2-(4-哌嗪-1-基-苯基胺基)-7,8-二氫-吡啶[2,3-d]嘧啶-6-氰基及其用於治療增生性疾病的用途
WO2020140053A1 (en) * 2018-12-28 2020-07-02 Spv Therapeutics Inc. Cyclin-dependent kinase inhibitors
AU2019413683B2 (en) * 2018-12-28 2025-05-22 Spv Therapeutics Inc. Cyclin-dependent kinase inhibitors
CN114340634A (zh) * 2019-07-02 2022-04-12 诺维逊生物股份有限公司 作为激酶抑制剂的杂环化合物
US11697648B2 (en) 2019-11-26 2023-07-11 Theravance Biopharma R&D Ip, Llc Fused pyrimidine pyridinone compounds as JAK inhibitors
US20230132667A1 (en) * 2020-05-28 2023-05-04 University Of Washington Drug-like molecules and methods for the therapeutic targeting of viral rna structures
KR20240115979A (ko) 2021-11-08 2024-07-26 프로젠토스 테라퓨틱스, 인크. 혈소판-유래 성장 인자 수용체(pdgfr) 알파 억제제 및 이의 용도
JP2024542205A (ja) * 2021-11-18 2024-11-13 オンコノヴァ セラピューティクス, インコーポレイテッド がんを処置するための方法および組成物
EP4433060A1 (en) * 2021-11-18 2024-09-25 Onconova Therapeutics, Inc. Methods and compositions for treating cancer
WO2023230288A1 (en) * 2022-05-25 2023-11-30 Onconova Therapeutics, Inc. Methods and compositions for treating cancer
WO2024107730A1 (en) * 2022-11-14 2024-05-23 Onconova Therapeutics, Inc. Methods and compositions for treating cancer
EP4618992A1 (en) * 2022-11-17 2025-09-24 Onconova Therapeutics, Inc. Methods and compositions for treating cancer

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080004285A1 (en) 2004-12-30 2008-01-03 De Jonghe Steven C A Pyrido(3,2-d)pyrimidines and pharmaceutical compositions useful for medical treatment
US20090062274A1 (en) 2005-10-07 2009-03-05 Exelixis, Inc Pyridopyrimidinone inhibitors of pi3kalpha

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5620981A (en) 1995-05-03 1997-04-15 Warner-Lambert Company Pyrido [2,3-D]pyrimidines for inhibiting protein tyrosine kinase mediated cellular proliferation
US6498163B1 (en) 1997-02-05 2002-12-24 Warner-Lambert Company Pyrido[2,3-D]pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation
ES2310039T3 (es) * 1998-05-26 2008-12-16 Warner-Lambert Company Llc Pirimidinas biciclicas y 3,4-dihidropirimidinas biciclicas como inhibidores de la proliferacion celular.
PL357634A1 (en) * 2000-01-27 2004-07-26 Warner-Lambert Company Pyridopyrimidinone derivatives for treatment of neurodegenerative disease
CN1438890A (zh) 2000-02-25 2003-08-27 弗·哈夫曼-拉罗切有限公司 腺苷受体调制剂
SK12472002A3 (sk) 2000-03-06 2003-04-01 Warner-Lambert Company 5-Alkylpyrido[2,3-d]pyrimidínové inhibítory tyrosínových kináz
JP4291696B2 (ja) 2002-01-22 2009-07-08 ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー 2−(ピリジン−2−イルアミノ)−ピリド[2,3−d]ピリミジン−7−オン
CA2555724A1 (en) 2004-02-18 2005-09-09 Warner-Lambert Company Llc 2-(pyridin-3-ylamino)-pyrido[2,3-d]pyrimidin-7-ones
WO2005105097A2 (en) 2004-04-28 2005-11-10 Gpc Biotech Ag Pyridopyrimidines for treating inflammatory and other diseases
US20060142312A1 (en) 2004-12-23 2006-06-29 Pfizer Inc C6-aryl and heteroaryl substituted pyrido[2,3-D] pyrimidin-7-ones
RU2007128961A (ru) * 2004-12-30 2009-02-10 4 Аза Ип Ив (Be) ПИРИДО(3,2-d)ПИРИМИДИНЫ И ФАРМАЦЕВТИЧЕСКИЕ ПРЕПАРАТЫ, ПОЛЕЗНЫЕ ДЛЯ КОНСЕРВАТИВНОГО ЛЕЧЕНИЯ
EP1899332A1 (en) * 2005-06-24 2008-03-19 Gilead Sciences, Inc. Pyrido(3,2-d)pyrimidines and pharmaceutical compositions useful for treating hepatitis c.
EP1940839B1 (en) * 2005-10-07 2013-07-31 Exelixis, Inc. PYRIDOPYRIMIDINONE INHIBITORS OF PI3Kalpha
US20090191193A1 (en) 2006-08-02 2009-07-30 Temple University-Of The Commonwealth System Of Higher Education Aryl Vinyl Sulfides, Sulfones, Sulfoxides and Sulfonamides, Derivatives Thereof and Therapeutic Uses Thereof
EP2084159A1 (en) 2006-10-16 2009-08-05 GPC Biotech Inc. Pyrido ý2, 3-d¨pyrimidines and their use as kinase inhibitors
WO2008150260A1 (en) 2007-06-06 2008-12-11 Gpc Biotech, Inc. 8-oxy-2-aminopyrido (2, 3-d) pyrimidin-7-one derivatives as kinase inhibitors and anticancer agents
WO2011075616A1 (en) 2009-12-18 2011-06-23 Temple University - Of The Commonwealth System Of Higher Education Substituted pyrido[2,3-d]pyrimidin-7(8h)-ones and therapeutic uses thereof
BR112013002375B1 (pt) * 2010-08-05 2020-05-12 Temple University - Of The Commonwealth System Of Higher Education Composto, processo de preparação do mesmo, composição farmacêutica, e, usos de um composto

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080004285A1 (en) 2004-12-30 2008-01-03 De Jonghe Steven C A Pyrido(3,2-d)pyrimidines and pharmaceutical compositions useful for medical treatment
US20090062274A1 (en) 2005-10-07 2009-03-05 Exelixis, Inc Pyridopyrimidinone inhibitors of pi3kalpha

Also Published As

Publication number Publication date
DK2600719T3 (da) 2014-12-15
US8987267B2 (en) 2015-03-24
US20130131058A1 (en) 2013-05-23
EP2600719B1 (en) 2014-10-08
EA022527B1 (ru) 2016-01-29
CA2807498A1 (en) 2012-02-09
EP2600719A1 (en) 2013-06-12
CN103200822A (zh) 2013-07-10
IL224555A (en) 2016-03-31
PL2600719T3 (pl) 2015-03-31
EP2600719A4 (en) 2014-01-01
PT2600719E (pt) 2014-12-22
EA201390199A1 (ru) 2013-07-30
CN103200822B (zh) 2014-12-24
AU2011286282B2 (en) 2014-08-21
NZ606281A (en) 2014-09-26
JP5512894B2 (ja) 2014-06-04
KR20130098314A (ko) 2013-09-04
WO2012018540A1 (en) 2012-02-09
BR112013002375A2 (pt) 2016-05-24
JP2013538196A (ja) 2013-10-10
MX2013001427A (es) 2013-06-13
BR112013002375B1 (pt) 2020-05-12
CA2807498C (en) 2017-02-07
AU2011286282A1 (en) 2013-02-14
ES2525866T3 (es) 2014-12-30

Similar Documents

Publication Publication Date Title
KR101434841B1 (ko) 2-치환-8-알킬-7-옥소-7,8-디하이드로피리도[2,3-d] 피리미딘-6-카르보니트릴 및 이의 용도
US8765755B2 (en) N-containing heterocyclic compounds
JP2013502404A (ja) ホスホイノシチド3−キナーゼ阻害剤としての三環式複素環化合物
KR20190104632A (ko) 트라이사이클릭 자이라제 억제제
EP1325009B1 (en) Amino-substituted tetracyclic compounds useful as anti-inflammatory agents and pharmaceutical compositions comprising same
AU2002211827A1 (en) Amino-substituted tetracyclic compounds useful as anti-inflammatory agents and pharmaceutical compositions comprising same
KR101754664B1 (ko) 치환된 피리도〔2,3-d〕피리미딘-7(8h)-온스 및 이의 치료 용도
ES2747423T3 (es) Compuesto de quinoxalina
CN116528871A (zh) 一种吡唑并喹唑啉类化合物、其制备方法及应用
CA2994036A1 (en) Novel fused pyrimidinone and triazinone derivatives, their process of preparation and their therapeutic uses as antifungal and/or antiparasitic agents
CN111868060B (zh) 二氢吡啶并酞嗪酮衍生物、其制备方法及应用
CN108912095B (zh) 苯并咪唑类化合物及其制备方法和应用
CN111825694A (zh) 稠环化合物、其制备方法及用途
AU2010330863B2 (en) Substituted pyrido[2,3-d]pyrimidin-7(8H)-ones and therapeutic uses thereof
WO2013142010A1 (en) 3-AMINOTHIENO[3,2-c]QUINOLINE DERIVATIVES, METHODS OF PREPARATION AND USES

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20130227

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
A201 Request for examination
A302 Request for accelerated examination
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20140226

Comment text: Request for Examination of Application

PA0302 Request for accelerated examination

Patent event date: 20140226

Patent event code: PA03022R01D

Comment text: Request for Accelerated Examination

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20140708

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20140821

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20140822

End annual number: 3

Start annual number: 1

PG1601 Publication of registration
FPAY Annual fee payment

Payment date: 20170810

Year of fee payment: 4

PR1001 Payment of annual fee

Payment date: 20170810

Start annual number: 4

End annual number: 4

FPAY Annual fee payment

Payment date: 20180808

Year of fee payment: 5

PR1001 Payment of annual fee

Payment date: 20180808

Start annual number: 5

End annual number: 5

FPAY Annual fee payment

Payment date: 20190808

Year of fee payment: 6

PR1001 Payment of annual fee

Payment date: 20190808

Start annual number: 6

End annual number: 6

PR1001 Payment of annual fee

Payment date: 20200812

Start annual number: 7

End annual number: 7

PR1001 Payment of annual fee

Payment date: 20210811

Start annual number: 8

End annual number: 8

PR1001 Payment of annual fee

Payment date: 20220805

Start annual number: 9

End annual number: 9

PR1001 Payment of annual fee

Payment date: 20230808

Start annual number: 10

End annual number: 10