CN105814043B - 用作tnf活性调节剂的三唑并吡啶衍生物 - Google Patents

用作tnf活性调节剂的三唑并吡啶衍生物 Download PDF

Info

Publication number
CN105814043B
CN105814043B CN201480067043.XA CN201480067043A CN105814043B CN 105814043 B CN105814043 B CN 105814043B CN 201480067043 A CN201480067043 A CN 201480067043A CN 105814043 B CN105814043 B CN 105814043B
Authority
CN
China
Prior art keywords
base
alkyl
methyl
amino
group
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
CN201480067043.XA
Other languages
English (en)
Chinese (zh)
Other versions
CN105814043A (zh
Inventor
D·C·布鲁金斯
V·E·杰克逊
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.)
UCB Biopharma SRL
Original Assignee
UCB SA
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 UCB SA filed Critical UCB SA
Publication of CN105814043A publication Critical patent/CN105814043A/zh
Application granted granted Critical
Publication of CN105814043B publication Critical patent/CN105814043B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • 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
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/53751,4-Oxazines, e.g. morpholine
    • A61K31/53771,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • 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
    • 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
    • A61P3/00Drugs for disorders of the metabolism
    • 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
    • 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
    • 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)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Cardiology (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Vascular Medicine (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Ophthalmology & Optometry (AREA)
  • Rheumatology (AREA)
  • Urology & Nephrology (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CN201480067043.XA 2013-12-09 2014-12-08 用作tnf活性调节剂的三唑并吡啶衍生物 Expired - Fee Related CN105814043B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB1321742.7A GB201321742D0 (en) 2013-12-09 2013-12-09 Therapeutic agents
GB1321742.7 2013-12-09
PCT/EP2014/076832 WO2015086496A1 (en) 2013-12-09 2014-12-08 Triazolopyridine derivatives as modulators of tnf activity

Publications (2)

Publication Number Publication Date
CN105814043A CN105814043A (zh) 2016-07-27
CN105814043B true CN105814043B (zh) 2019-05-17

Family

ID=50000425

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201480067043.XA Expired - Fee Related CN105814043B (zh) 2013-12-09 2014-12-08 用作tnf活性调节剂的三唑并吡啶衍生物

Country Status (11)

Country Link
US (1) US9850240B2 (https=)
EP (1) EP3080109B1 (https=)
JP (1) JP6426185B2 (https=)
CN (1) CN105814043B (https=)
BR (1) BR112016011844B1 (https=)
CA (1) CA2931578C (https=)
ES (1) ES2730942T3 (https=)
GB (1) GB201321742D0 (https=)
RU (1) RU2677697C1 (https=)
TR (1) TR201907702T4 (https=)
WO (1) WO2015086496A1 (https=)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201321735D0 (en) * 2013-12-09 2014-01-22 Ucb Pharma Sa Therapeutic Agents
CA2982446A1 (en) 2015-03-18 2016-09-22 Bristol-Myers Squibb Company Tricyclic heterocyclic compounds useful as inhibitors of tnf
AU2016233288A1 (en) 2015-03-18 2017-11-09 Bristol-Myers Squibb Company Substituted tricyclic heterocyclic compounds
MX2017011577A (es) 2015-03-18 2017-10-26 Bristol Myers Squibb Co Compuestos heterociclicos utiles como inhibidores de factor de necrosis tumoral (tnf).
US9879016B2 (en) 2015-04-17 2018-01-30 Abbvie Inc. Indazolones as modulators of TNF signaling
AR104291A1 (es) 2015-04-17 2017-07-12 Abbvie Inc Moduladores tricíclicos de la señalización por tnf
US20160304496A1 (en) 2015-04-17 2016-10-20 Abbvie Inc. Indazolones as modulators of tnf signaling
GB201510758D0 (en) 2015-06-18 2015-08-05 Ucb Biopharma Sprl Novel TNFa structure for use in therapy
KR102679517B1 (ko) 2015-08-03 2024-06-27 브리스톨-마이어스 스큅 컴퍼니 Tnf 알파의 조정제로서 유용한 시클릭 화합물
GB201621907D0 (en) 2016-12-21 2017-02-01 Ucb Biopharma Sprl And Sanofi Antibody epitope
WO2018119142A1 (en) 2016-12-21 2018-06-28 Amgen Inc. Anti-tnf alpha antibody formulations
CN111770924B (zh) * 2018-04-04 2023-05-09 深圳福沃药业有限公司 用于治疗乳腺癌的雌激素受体降解剂

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060281750A1 (en) * 2005-06-09 2006-12-14 Li James J Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors
WO2008045393A2 (en) * 2006-10-11 2008-04-17 Amgen Inc. Imidazo- and triazolo-pyridine compounds and methods of use therof
US20090093516A1 (en) * 2007-10-01 2009-04-09 Bristol-Myers Squibb Company Triazolopyridine 11-beta hydroxysteroid dehydrogenase type i inhibitors
FR2933980A1 (fr) * 2008-07-18 2010-01-22 Sanofi Aventis Nouveaux derives triazolo°4,3-a!pyridine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met
WO2010022076A1 (en) * 2008-08-19 2010-02-25 Array Biopharma Inc. Triazolopyridine compounds as pim kinase inhibitors
WO2010022081A1 (en) * 2008-08-19 2010-02-25 Array Biopharma Inc. Triazolopyridine compounds as pim kinase inhibitors
WO2012065297A1 (en) * 2010-11-16 2012-05-24 Impact Therapeutics, Inc. 3-ARYL-6-ARYL-[1,2,4]TRIAZOLO[4,3-a]PYRIDINES AS INHIBITORS OF CELL PROLIFERATION AND THE USE THEREOF
CN103130792A (zh) * 2011-11-30 2013-06-05 江苏正大天晴药业股份有限公司 一种2-氨基噻唑类化合物
WO2013083206A1 (en) * 2011-12-09 2013-06-13 Chiesi Farmaceutici S.P.A. Derivatives of 4-hydroxy-1,2,3,4-tetrahydronaphtalen-1-yl urea and their use in the treatment of, inter alia, diseases of the respiratory tract
WO2013138687A1 (en) * 2012-03-16 2013-09-19 Bristol-Myers Squibb Company Positive allosteric modulators of mglur2

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2601952B1 (fr) * 1986-07-23 1988-11-25 Carpibem Nouveaux derives amino alkyl thio de triazolopyridine ou triazoloquinoline, leurs procedes de preparation, medicaments les contenant, utiles notamment comme antalgiques
DE10038019A1 (de) * 2000-08-04 2002-02-14 Bayer Ag Substituierte Triazolopyrid(az)ine
HUP0303415A2 (hu) * 2001-03-09 2004-01-28 Pfizer Products Inc. Triazolopiridinek, mint gyulladásgátló anyagok és ezeket tartalmazó gyógyszerkészítmények
CN2783538Y (zh) 2004-08-04 2006-05-24 蒋沛康 无电线电池按扣
US20090209577A1 (en) * 2004-08-18 2009-08-20 Pfizer Inc. Novel Triazolopyridine Compounds
US7579360B2 (en) * 2005-06-09 2009-08-25 Bristol-Myers Squibb Company Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors
US8217177B2 (en) * 2006-07-14 2012-07-10 Amgen Inc. Fused heterocyclic derivatives and methods of use
PE20080403A1 (es) * 2006-07-14 2008-04-25 Amgen Inc Derivados heterociclicos fusionados y metodos de uso
US8324241B2 (en) * 2008-04-11 2012-12-04 Bristol-Myers Squibb Company Triazolo compounds useful as DGAT1 inhibitors
JP2011528337A (ja) * 2008-07-18 2011-11-17 サノフイ−アベンテイス 新規トリアゾロ[4,3−a]ピリジン誘導体、これらの調製方法、医薬としてのこれらの使用、医薬組成物および、特にmet阻害剤としての、新規使用
DE102008063667A1 (de) * 2008-12-18 2010-07-01 Merck Patent Gmbh 3-(3-Pyrimidin-2-yl-benzyl)-°[1,2,4]triazolo[4,3-b]pyrimidin-derivate
CA2752693A1 (en) * 2009-02-17 2010-08-26 Chiesi Farmaceutici S.P.A. Triazolopyridine derivatives as p38 map kinase inhibitors
ES2642586T3 (es) * 2009-07-27 2017-11-16 Gilead Sciences, Inc. Compuestos heterocíclicos condensados como moduladores de canales iónicos
FR2966471A1 (fr) * 2010-09-20 2012-04-27 Valeo Vision Piece de vehicule automobile en materiau a base de polymere (s) traite en surface
CA2848809A1 (en) * 2011-09-15 2013-03-21 Novartis Ag 6-substituted 3-(quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyradines as c-met tyrosine kinase
US9340549B2 (en) * 2012-03-05 2016-05-17 Amgen Inc. Oxazolidinone compounds and derivatives thereof
BR112014030940B1 (pt) 2012-06-11 2022-09-06 UCB Biopharma SRL Benzimidazóis que modulam tnf-alfa e composição farmacêutica compreendendo os mesmos
GB201212513D0 (en) 2012-07-13 2012-08-29 Ucb Pharma Sa Therapeutic agents
CN104619709B (zh) 2012-07-13 2016-11-09 Ucb生物制药私人有限公司 作为tnf活性调节剂的咪唑并吡啶衍生物

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060281750A1 (en) * 2005-06-09 2006-12-14 Li James J Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors
WO2008045393A2 (en) * 2006-10-11 2008-04-17 Amgen Inc. Imidazo- and triazolo-pyridine compounds and methods of use therof
US20090093516A1 (en) * 2007-10-01 2009-04-09 Bristol-Myers Squibb Company Triazolopyridine 11-beta hydroxysteroid dehydrogenase type i inhibitors
FR2933980A1 (fr) * 2008-07-18 2010-01-22 Sanofi Aventis Nouveaux derives triazolo°4,3-a!pyridine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met
WO2010022076A1 (en) * 2008-08-19 2010-02-25 Array Biopharma Inc. Triazolopyridine compounds as pim kinase inhibitors
WO2010022081A1 (en) * 2008-08-19 2010-02-25 Array Biopharma Inc. Triazolopyridine compounds as pim kinase inhibitors
WO2012065297A1 (en) * 2010-11-16 2012-05-24 Impact Therapeutics, Inc. 3-ARYL-6-ARYL-[1,2,4]TRIAZOLO[4,3-a]PYRIDINES AS INHIBITORS OF CELL PROLIFERATION AND THE USE THEREOF
CN103130792A (zh) * 2011-11-30 2013-06-05 江苏正大天晴药业股份有限公司 一种2-氨基噻唑类化合物
WO2013083206A1 (en) * 2011-12-09 2013-06-13 Chiesi Farmaceutici S.P.A. Derivatives of 4-hydroxy-1,2,3,4-tetrahydronaphtalen-1-yl urea and their use in the treatment of, inter alia, diseases of the respiratory tract
WO2013138687A1 (en) * 2012-03-16 2013-09-19 Bristol-Myers Squibb Company Positive allosteric modulators of mglur2

Also Published As

Publication number Publication date
JP2016539971A (ja) 2016-12-22
WO2015086496A1 (en) 2015-06-18
TR201907702T4 (tr) 2019-06-21
US20160304512A1 (en) 2016-10-20
US9850240B2 (en) 2017-12-26
CA2931578C (en) 2021-10-26
RU2677697C1 (ru) 2019-01-21
EP3080109B1 (en) 2019-05-15
JP6426185B2 (ja) 2018-11-21
RU2016127228A (ru) 2018-01-23
GB201321742D0 (en) 2014-01-22
BR112016011844B1 (pt) 2022-08-16
ES2730942T3 (es) 2019-11-13
CN105814043A (zh) 2016-07-27
CA2931578A1 (en) 2015-06-18
BR112016011844A2 (https=) 2017-08-08
EP3080109A1 (en) 2016-10-19

Similar Documents

Publication Publication Date Title
CN105814041B (zh) 用作tnf活性调节剂的苯并三唑衍生物
CN105814043B (zh) 用作tnf活性调节剂的三唑并吡啶衍生物
CN105814025B (zh) 用作tnf活性调节剂的四氢苯并咪唑衍生物
JP7554672B2 (ja) Irak分解剤およびそれらの使用
CN112135824B (zh) 作为免疫调节剂的杂环化合物
CN102971317B (zh) 四氢-吡啶并-嘧啶衍生物
CN102015705B (zh) 稠合的杂环衍生物及其用途
CN105189494B (zh) 作为ssao抑制剂的咪唑并[4,5‑c]吡啶和吡咯并[2,3‑c]吡啶衍生物
CA3150108A1 (en) Hpk1 antagonists and uses thereof
KR20220145325A (ko) Irak 분해제 및 이의 용도
WO2020251972A1 (en) Smarca degraders and uses thereof
CA3121236A1 (en) 2-oxoquinazoline derivatives as methionine adenosyltransferase 2a inhibitors
CN109195969A (zh) 作为tnf活性调节剂的稠合五环咪唑衍生物
JP2022516401A (ja) Irak分解剤およびそれらの使用
AU2018389145B2 (en) Exo-aza spiro inhibitors of menin-MLL interaction
EP3833439B1 (en) Benzimidazole inhibitors of pad enzymes
KR20230130179A (ko) Irak 분해제 및 그 용도
CN105814051B (zh) 用作tnf活性调节剂的四氢咪唑并吡啶衍生物
KR20160135283A (ko) 5-치환된 인다졸-3-카르복스아미드 및 이의 제조 및 용도
BR112020015328A2 (pt) Inibidores de gcn2 e usos dos mesmos
CA3192393A1 (en) Piperidinyl small molecule degraders of helios and methods of use
CN109219609A (zh) 作为tnf活性调节剂的稠合六环咪唑衍生物
TW201016676A (en) Heterocyclic derivatives and methods of use thereof
CN109195968A (zh) 作为tnf活性调节剂的稠合五环咪唑衍生物
AU2024334386A1 (en) Stat6 degraders and uses thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CP01 Change in the name or title of a patent holder

Address after: Brussels

Patentee after: UCB biopharmaceutical Co.,Ltd.

Address before: Brussels

Patentee before: UCB BIOPHARMA SPRL

CP01 Change in the name or title of a patent holder
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20190517

CF01 Termination of patent right due to non-payment of annual fee