CA3009937C - Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases - Google Patents

Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases Download PDF

Info

Publication number
CA3009937C
CA3009937C CA3009937A CA3009937A CA3009937C CA 3009937 C CA3009937 C CA 3009937C CA 3009937 A CA3009937 A CA 3009937A CA 3009937 A CA3009937 A CA 3009937A CA 3009937 C CA3009937 C CA 3009937C
Authority
CA
Canada
Prior art keywords
alkyl
groups
chloro
ethyl
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
CA3009937A
Other languages
English (en)
French (fr)
Other versions
CA3009937A1 (en
Inventor
Kiyoshi Kanazawa
Kazuhiko Nonomura
Takako Okumura
Shinichi Koizumi
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.)
Askat Inc
Original Assignee
Askat 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 Askat Inc filed Critical Askat Inc
Publication of CA3009937A1 publication Critical patent/CA3009937A1/en
Application granted granted Critical
Publication of CA3009937C publication Critical patent/CA3009937C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/38Heterocyclic compounds having sulfur as a ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/38Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381Heterocyclic compounds having sulfur as a ring hetero atom having five-membered 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
    • A61K31/435Heterocyclic 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
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4412Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
    • 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/443Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • A61P31/08Antibacterial agents for leprosy
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • 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
    • 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
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Pain & Pain Management (AREA)
  • Transplantation (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pulmonology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA3009937A 2010-02-22 2011-02-22 Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases Active CA3009937C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US28250610P 2010-02-22 2010-02-22
US61/282,506 2010-02-22
CA2789665A CA2789665C (en) 2010-02-22 2011-02-22 Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2789665A Division CA2789665C (en) 2010-02-22 2011-02-22 Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases

Publications (2)

Publication Number Publication Date
CA3009937A1 CA3009937A1 (en) 2011-08-25
CA3009937C true CA3009937C (en) 2020-12-15

Family

ID=44482754

Family Applications (2)

Application Number Title Priority Date Filing Date
CA3009937A Active CA3009937C (en) 2010-02-22 2011-02-22 Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases
CA2789665A Active CA2789665C (en) 2010-02-22 2011-02-22 Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2789665A Active CA2789665C (en) 2010-02-22 2011-02-22 Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases

Country Status (12)

Country Link
US (1) US9457084B2 (enExample)
EP (1) EP2538978B1 (enExample)
JP (2) JP6152643B2 (enExample)
KR (1) KR101780666B1 (enExample)
CN (2) CN102770159A (enExample)
BR (1) BR112012020236A2 (enExample)
CA (2) CA3009937C (enExample)
ES (1) ES2600355T3 (enExample)
HK (1) HK1249401A1 (enExample)
MX (1) MX341482B (enExample)
RU (1) RU2571816C2 (enExample)
WO (1) WO2011102149A1 (enExample)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR091429A1 (es) * 2012-06-29 2015-02-04 Lilly Co Eli Compuestos de fenoxietil piperidina
UA115576C2 (uk) * 2012-12-06 2017-11-27 Байєр Фарма Акцієнгезелльшафт Похідні бензимідазолу як антагоністи ер4
EP2765128A1 (en) * 2013-02-07 2014-08-13 Almirall, S.A. Substituted benzamides with activity towards EP4 receptors
TW201443004A (zh) 2013-02-15 2014-11-16 Lilly Co Eli 苯氧基乙氧基化合物
TWI636046B (zh) 2013-05-17 2018-09-21 美國禮來大藥廠 苯氧基乙基二氫-1h-異喹啉化合物
CN105793242B (zh) 2013-12-17 2018-02-16 伊莱利利公司 苯氧基乙基环状胺衍生物及其作为ep4受体调节剂的活性
TW201607943A (zh) * 2013-12-19 2016-03-01 拜耳製藥公司 作為ep4配體之新穎苯并咪唑衍生物
CN105939713A (zh) 2014-03-06 2016-09-14 阿莱塔纳治疗学股份有限公司 格拉匹纶组合物及其使用方法
US12109218B2 (en) 2014-12-09 2024-10-08 Aratana Therapeutics, Inc. Compositions of grapiprant and methods for using the same
CA3002144C (en) * 2015-10-16 2024-01-23 Eisai R&D Management Co., Ltd. Ep4 antagonists
US10342785B2 (en) * 2016-11-04 2019-07-09 Askat Inc. Use of EP4 receptor antagonists for the treatment of NASH-associated liver cancer
CA3047336A1 (en) 2017-01-23 2018-07-26 Jecure Therapeutics, Inc. Chemical compounds as inhibitors of interleukin-1 activity
CN109836434B (zh) * 2017-11-27 2020-09-25 上海宇耀生物科技有限公司 噻吩并环类化合物及其合成方法和应用
AU2019255196A1 (en) 2018-04-16 2020-11-12 Arrys Therapeutics, Inc. EP4 inhibitors and use thereof
US10239885B1 (en) 2018-06-18 2019-03-26 Avista Pharma Solutions, Inc. Compound 1-[2-[4-(2-ethyl-6,8-dimethylimidazo[1,2-α]pyrazin-3-yl)phenyl]ethyl]-3-(p-tolylsulfonyl)urea as a prostaglandin EP4 receptor antagonist
US20210315909A1 (en) 2018-07-11 2021-10-14 Arrys Therapeutics, Inc. Polymorphic compounds and uses thereof
BR112021001044A2 (pt) 2018-07-20 2021-04-13 F. Hoffmann-La Roche Ag Compostos de sulfonimidamida como inibidores da atividade de interleucina-1
CA3104199A1 (en) * 2018-07-20 2020-01-23 F. Hoffmann-La Roche Ag Sulfonylurea compounds as inhibitors of interleukin-1 activity
PT3860998T (pt) 2018-10-05 2024-04-02 Annapurna Bio Inc Compostos e composições para o tratamento de condições associadas à atividade do recetor apj
EP3917935A4 (en) 2019-01-30 2022-11-16 Avista Pharma Solutions, Inc. SYNTHESIS PROCESS AND NEW INTERMEDIATES
US11459331B2 (en) 2019-01-30 2022-10-04 Avista Pharma Solutions, Inc. Chemical compounds
JP7843705B2 (ja) 2020-01-22 2026-04-10 エフ・ホフマン-ラ・ロシュ・アクチェンゲゼルシャフト Nlrp3モジュレーターとしてのスルホンイミドアミド化合物
WO2021205367A1 (en) * 2020-04-08 2021-10-14 Askat Inc. Use of ep4 receptor antagonists for the treatment of liver cancer, melanoma, lymphoma and leukemia

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HN2001000224A (es) 2000-10-19 2002-06-13 Pfizer Compuestos de imidazol condensado con arilo o heteroarilo como agentes anti - inflamatorios y analgesicos.
IL164263A0 (en) 2002-04-12 2005-12-18 Pfizer Use of ep4 receptor ligands on the treatment of il-6 involved diseases
GB0302094D0 (en) 2003-01-29 2003-02-26 Pharmagene Lab Ltd EP4 receptor antagonists
DK1603893T3 (da) * 2003-01-29 2008-09-08 Asterand Uk Ltd EP4 -Receptorantagonister
RS20060143A (sr) * 2003-09-03 2008-06-05 Pfizer Inc., Jedinjenja fenil ili piridil amida kao antagonisti prostaglandina e2
CN1946391A (zh) * 2004-04-20 2007-04-11 辉瑞产品公司 包含α-2-δ配体的组合
MXPA06011555A (es) * 2004-05-04 2006-12-15 Pfizer Compuestos de metil-aril o heteroaril-amida sustituida.
RU2357968C1 (ru) * 2005-03-11 2009-06-10 Раквалиа Фарма Инк. Кристаллические формы производной имидазола
EP1886987A1 (en) * 2006-08-11 2008-02-13 Givaudan S.A. Process for producing 2,2,3-trimethylcyclopent-3-enecarbaldehyde (campholytic aldehyde)
WO2008017164A1 (en) * 2006-08-11 2008-02-14 Merck Frosst Canada Ltd. Thiophenecarboxamide derivatives as ep4 receptor ligands

Also Published As

Publication number Publication date
US20120316197A1 (en) 2012-12-13
EP2538978A1 (en) 2013-01-02
JP2013520397A (ja) 2013-06-06
MX2012009503A (es) 2012-09-12
HK1249401A1 (zh) 2018-11-02
CN107693518A (zh) 2018-02-16
KR20130040787A (ko) 2013-04-24
JP6152643B2 (ja) 2017-06-28
WO2011102149A1 (en) 2011-08-25
RU2571816C2 (ru) 2015-12-20
CA2789665C (en) 2020-06-16
MX341482B (es) 2016-08-22
CA3009937A1 (en) 2011-08-25
BR112012020236A2 (pt) 2016-05-17
KR101780666B1 (ko) 2017-09-21
EP2538978A4 (en) 2013-10-16
EP2538978B1 (en) 2016-09-07
CN102770159A (zh) 2012-11-07
JP2017095511A (ja) 2017-06-01
CA2789665A1 (en) 2011-08-25
HK1178088A1 (zh) 2013-09-06
RU2012140450A (ru) 2014-03-27
US9457084B2 (en) 2016-10-04
ES2600355T3 (es) 2017-02-08

Similar Documents

Publication Publication Date Title
CA2789665C (en) Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases
US10786490B2 (en) Use of EP4 receptor antagonists in the treatment of cartilage disease
US20220313668A1 (en) Method of treating liver fibrosis
US10391086B2 (en) Use of EP4 receptor antagonists in the treatment of cartilage disease
HK1177148A (en) Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases
HK1212211B (zh) Ep4受体拮抗剂在软骨疾病的治疗中的用途
HK1178088B (en) Use of an ep4 receptor antagonist in the treatment of allergic contact dermatitis and psoriasis

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20180831

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 14TH ANNIV.) - STANDARD

Year of fee payment: 14

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241206

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20241206

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20241206

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 15TH ANNIV.) - STANDARD

Year of fee payment: 15

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20251209

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20251209