KR100948453B1 - Bcr-abl 키나아제 억제제인 신규한페닐아미노피리미딘 유도체 - Google Patents

Bcr-abl 키나아제 억제제인 신규한페닐아미노피리미딘 유도체 Download PDF

Info

Publication number
KR100948453B1
KR100948453B1 KR1020077008040A KR20077008040A KR100948453B1 KR 100948453 B1 KR100948453 B1 KR 100948453B1 KR 1020077008040 A KR1020077008040 A KR 1020077008040A KR 20077008040 A KR20077008040 A KR 20077008040A KR 100948453 B1 KR100948453 B1 KR 100948453B1
Authority
KR
South Korea
Prior art keywords
methyl
formula
delete delete
single bond
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
KR1020077008040A
Other languages
English (en)
Korean (ko)
Other versions
KR20070106681A (ko
Inventor
아말라 키샨 콤펠라
칼리 사트야 브후잔가 라오 아디브하틀라
스리니바스 라카콘다
크하드가파띠 포딜리
초우다리 난나파네니 벤카이아
Original Assignee
낫코 파마 리미티드
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 낫코 파마 리미티드 filed Critical 낫코 파마 리미티드
Publication of KR20070106681A publication Critical patent/KR20070106681A/ko
Application granted granted Critical
Publication of KR100948453B1 publication Critical patent/KR100948453B1/ko
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • 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
    • C07D401/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K31/506Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/64Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/66Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/18Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/44Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81Amides; Imides
    • C07D213/82Amides; Imides in position 3
    • 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
    • C07D401/14Heterocyclic 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 three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
KR1020077008040A 2004-09-09 2005-07-19 Bcr-abl 키나아제 억제제인 신규한페닐아미노피리미딘 유도체 Expired - Fee Related KR100948453B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN908/CHE/2004 2004-09-09
IN908CH2004 2004-09-09
PCT/IN2005/000243 WO2006027795A1 (en) 2004-09-09 2005-07-19 Novel phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase

Publications (2)

Publication Number Publication Date
KR20070106681A KR20070106681A (ko) 2007-11-05
KR100948453B1 true KR100948453B1 (ko) 2010-03-17

Family

ID=35395645

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020077008040A Expired - Fee Related KR100948453B1 (ko) 2004-09-09 2005-07-19 Bcr-abl 키나아제 억제제인 신규한페닐아미노피리미딘 유도체

Country Status (25)

Country Link
US (2) US7910598B2 (https=)
EP (2) EP1786799B1 (https=)
JP (1) JP5184887B2 (https=)
KR (1) KR100948453B1 (https=)
CN (1) CN101068805B (https=)
AP (1) AP2470A (https=)
AU (1) AU2005281299B2 (https=)
BR (1) BRPI0515081B8 (https=)
CA (1) CA2591321C (https=)
CY (1) CY1113617T1 (https=)
DK (1) DK1786799T3 (https=)
EA (1) EA013328B1 (https=)
ES (1) ES2390227T3 (https=)
HR (1) HRP20070146B1 (https=)
IL (1) IL181811A (https=)
MA (1) MA28922B1 (https=)
MX (1) MX2007002819A (https=)
NO (1) NO337598B1 (https=)
NZ (1) NZ554361A (https=)
PL (1) PL1786799T3 (https=)
PT (1) PT1786799E (https=)
SI (1) SI1786799T1 (https=)
UA (1) UA94570C2 (https=)
WO (1) WO2006027795A1 (https=)
ZA (2) ZA200701942B (https=)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6667300B2 (en) * 2000-04-25 2003-12-23 Icos Corporation Inhibitors of human phosphatidylinositol 3-kinase delta
SI2612862T1 (sl) 2004-05-13 2017-04-26 Icos Corporation Kinazolini kot inhibitorji humane fosfatidilinozitol 3-kinaze delta
US20110190328A1 (en) * 2004-09-09 2011-08-04 Natco Pharma Limited Acid addition salts of (3,5-bis trifluoromethyl)-n-[4-methyl-3-(4-pyridin-3yl-pyrimidin-2ylamino)-phenyl]-benzamide
US8735415B2 (en) 2004-09-09 2014-05-27 Natco Pharma Limited Acid addition salts of (3,5-Bis trifluoromethyl)-N-[4-methyl-3-(4-pyridin-3yl-pyrimidin-2ylamino)-phenyl]-benzamide
UA94570C2 (en) 2004-09-09 2011-05-25 Натко Фарма Лимитед Phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase
US7939541B2 (en) * 2004-09-09 2011-05-10 Natco Pharma Limited Intermediates and a process employing the intermediates for the preparation of (3-trifluoromethylsulfonyl)-N-[4-methyl-3-(4-pyridin-3yl-pyrimidin-2ylamino)-phenyl]-benzamide
WO2008031534A1 (en) * 2006-09-11 2008-03-20 Syngenta Participations Ag Insecticidal compounds
WO2008058037A1 (en) * 2006-11-03 2008-05-15 Irm Llc Compounds and compositions as protein kinase inhibitors
ES2396160T3 (es) * 2006-12-14 2013-02-19 Bayer Intellectual Property Gmbh Derivados de DIHIDROPIRIDINA que utiliza como inhibidores de la proteina quinasa
EP2152688A1 (en) * 2007-05-04 2010-02-17 Irm Llc Compounds and compositions as c-kit and pdgfr kinase inhibitors
EP2148874B1 (en) * 2007-05-04 2012-02-08 Irm Llc Pyrimidine derivatives and compositions as c-kit and pdgfr kinase inhibitors
CA2697077C (en) 2007-08-22 2012-10-16 Irm Llc 2-heteroarylamino-pyrimidine derivatives as kinase inhibitors
CA2697081C (en) 2007-08-22 2013-04-23 Irm Llc 5-(4-(haloalkoxy)phenyl)pyrimidine-2-amine compounds and compositions as kinase inhibitors
US8067422B2 (en) 2008-03-04 2011-11-29 Natco Pharma Limited Crystal form of phenylamino pyrimidine derivatives
MY183331A (en) * 2008-03-04 2021-02-18 Natco Pharma Ltd Crystal form of phenylamino pyrimidine derivatives
WO2012004801A1 (en) * 2010-07-07 2012-01-12 Hetero Research Foundation Process for imatinib mesylate
GB2488788B (en) 2011-03-07 2013-07-10 Natco Pharma Ltd Oral formulation of phenylaminopyrymidine compound with enhanced bioavailability and pharmacological response
CN103797011B (zh) 2011-09-01 2016-03-30 诺华股份有限公司 作为c-Kit激酶抑制剂的化合物和组合物
US9061028B2 (en) 2012-02-15 2015-06-23 Natco Pharma Limited Process for the preparation of Nilotinib
CN104379582A (zh) * 2012-06-15 2015-02-25 巴斯夫欧洲公司 包含达沙替尼和所选择的共晶体形成剂的多组分晶体
PT3389633T (pt) 2015-12-18 2021-08-05 Natco Pharma Ltd Composições farmacêuticas compreendendo derivados de fenilaminopirimidina
US10722484B2 (en) 2016-03-09 2020-07-28 K-Gen, Inc. Methods of cancer treatment
JP2023534963A (ja) 2020-07-15 2023-08-15 サード ハーモニック バイオ, インコーポレイテッド 選択的c-kitキナーゼ阻害剤の結晶質形態
US11744823B2 (en) 2020-11-19 2023-09-05 Third Harmonic Bio, Inc. Pharmaceutical compositions of a selective c-kit kinase inhibitor and methods for making and using same
CN113125689B (zh) * 2021-03-29 2022-02-22 创芯国际生物科技(广州)有限公司 一种新型mtt细胞活力检测试剂盒及其应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999015164A1 (en) * 1997-09-23 1999-04-01 Zeneca Limited Amide derivatives for the treatment of diseases mediated by cytokines
WO2004029038A1 (en) 2002-09-27 2004-04-08 Novartis Ag Novel pyrimidineamide derivatives and the use thereof
WO2004110452A1 (en) 2003-06-13 2004-12-23 Novartis Ag 2-aminopyrimidine derivatives as raf kinase inhibitors

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW225528B (https=) 1992-04-03 1994-06-21 Ciba Geigy Ag
US5516775A (en) 1992-08-31 1996-05-14 Ciba-Geigy Corporation Further use of pyrimidine derivatives
KR100330553B1 (ko) 1993-10-01 2002-11-27 노파르티스 아게 약물학적활성피리딘유도체및그의제조방법
JPH08503971A (ja) 1993-10-01 1996-04-30 チバ−ガイギー アクチェンゲゼルシャフト ピリミジンアミン誘導体及びその調製のための方法
WO1995009851A1 (en) 1993-10-01 1995-04-13 Ciba-Geigy Ag Pharmacologically active pyrimidineamine derivatives and processes for the preparation thereof
CO4940418A1 (es) 1997-07-18 2000-07-24 Novartis Ag Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso
CA2338121A1 (en) * 1998-08-04 2000-02-17 Astrazeneca Ab Amide derivatives useful as inhibitors of the production of cytokines
GB0022438D0 (en) 2000-09-13 2000-11-01 Novartis Ag Organic Compounds
WO2004002963A1 (ja) * 2002-06-28 2004-01-08 Nippon Shinyaku Co., Ltd. アミド誘導体及び医薬
AU2003242988A1 (en) * 2003-06-06 2005-01-04 Adibhatla Kali Sathya Bhujanga Rao Process for the preparation of the anti-cancer drug imatinib and its analogues
UA94570C2 (en) 2004-09-09 2011-05-25 Натко Фарма Лимитед Phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase
WO2008058037A1 (en) * 2006-11-03 2008-05-15 Irm Llc Compounds and compositions as protein kinase inhibitors

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999015164A1 (en) * 1997-09-23 1999-04-01 Zeneca Limited Amide derivatives for the treatment of diseases mediated by cytokines
WO2004029038A1 (en) 2002-09-27 2004-04-08 Novartis Ag Novel pyrimidineamide derivatives and the use thereof
WO2004110452A1 (en) 2003-06-13 2004-12-23 Novartis Ag 2-aminopyrimidine derivatives as raf kinase inhibitors

Also Published As

Publication number Publication date
EP1786799B1 (en) 2012-07-04
CY1113617T1 (el) 2016-06-22
ZA200701942B (en) 2008-10-29
US20070232633A1 (en) 2007-10-04
MA28922B1 (fr) 2007-10-01
SI1786799T1 (sl) 2012-12-31
JP5184887B2 (ja) 2013-04-17
PL1786799T3 (pl) 2012-12-31
IL181811A (en) 2013-07-31
NZ554361A (en) 2009-03-31
ES2390227T3 (es) 2012-11-07
MX2007002819A (es) 2007-08-14
AP2007003944A0 (en) 2007-04-30
UA94570C2 (en) 2011-05-25
EA013328B1 (ru) 2010-04-30
AU2005281299A1 (en) 2006-03-16
IL181811A0 (en) 2007-07-04
NO337598B1 (no) 2016-05-09
DK1786799T3 (da) 2012-10-01
JP2008512448A (ja) 2008-04-24
HRP20070146A2 (en) 2007-08-31
EP2295424B1 (en) 2015-10-14
NO20071521L (no) 2007-06-11
US7910598B2 (en) 2011-03-22
US8183253B2 (en) 2012-05-22
WO2006027795A1 (en) 2006-03-16
PT1786799E (pt) 2012-09-18
CN101068805A (zh) 2007-11-07
AU2005281299B2 (en) 2012-03-15
ZA200703123B (en) 2008-10-29
EA200700601A1 (ru) 2008-02-28
HRP20070146B1 (hr) 2015-12-04
EP2295424A1 (en) 2011-03-16
CA2591321A1 (en) 2006-03-16
HK1110588A1 (en) 2008-07-18
CN101068805B (zh) 2013-04-03
KR20070106681A (ko) 2007-11-05
BRPI0515081A (pt) 2008-07-08
BRPI0515081B8 (pt) 2021-05-25
AP2470A (en) 2012-09-17
BRPI0515081B1 (pt) 2021-05-04
US20080306100A1 (en) 2008-12-11
CA2591321C (en) 2013-09-24
EP1786799A1 (en) 2007-05-23

Similar Documents

Publication Publication Date Title
KR100948453B1 (ko) Bcr-abl 키나아제 억제제인 신규한페닐아미노피리미딘 유도체
AU2003249962B2 (en) Inhibitors of tyrosine kinases
AU693114B2 (en) Pharmacologically active pyrimidineamine derivatives and processes for the preparation thereof
DE60315479T2 (de) Pyrimidinamid derivate und deren verwendung
NO316753B1 (no) Substituerte aza- og diazacykloheptan og -cyklooktan-forbindelser og deres anvendelser, samt farmasoytiske blandinger inneholdende slike forbindelser
JP2002508780A (ja) 新規な化合物
US20230131025A1 (en) Quinolyl phosphine oxide compound, and composition and application thereof
US10047088B2 (en) 1H-1,8-naphthyridin-2-ones as anti proliferative compounds
HK1110588B (en) Novel phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase
HK1150362A (en) Processes for the preparation of novel phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase
TW378208B (en) Pharmacologically active N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives
CN104370883A (zh) 一种三唑类抗真菌化合物及其盐类
JPH04235983A (ja) 新規キノリン誘導体およびそれを有効成分として含有する制癌剤効果増強剤

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

A201 Request for examination
E13-X000 Pre-grant limitation requested

St.27 status event code: A-2-3-E10-E13-lim-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

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

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

FPAY Annual fee payment

Payment date: 20130227

Year of fee payment: 4

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 4

FPAY Annual fee payment

Payment date: 20140227

Year of fee payment: 5

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 5

FPAY Annual fee payment

Payment date: 20150227

Year of fee payment: 6

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 6

FPAY Annual fee payment

Payment date: 20160108

Year of fee payment: 7

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 7

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 8

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

FPAY Annual fee payment

Payment date: 20180305

Year of fee payment: 9

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 9

FPAY Annual fee payment

Payment date: 20190226

Year of fee payment: 10

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 10

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 11

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 12

PC1903 Unpaid annual fee

St.27 status event code: A-4-4-U10-U13-oth-PC1903

Not in force date: 20220312

Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

PC1903 Unpaid annual fee

St.27 status event code: N-4-6-H10-H13-oth-PC1903

Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

Not in force date: 20220312