CA2811033C - N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors - Google Patents

N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors Download PDF

Info

Publication number
CA2811033C
CA2811033C CA2811033A CA2811033A CA2811033C CA 2811033 C CA2811033 C CA 2811033C CA 2811033 A CA2811033 A CA 2811033A CA 2811033 A CA2811033 A CA 2811033A CA 2811033 C CA2811033 C CA 2811033C
Authority
CA
Canada
Prior art keywords
indazole
oxo
piperidin
spiro
tetrahydro
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
CA2811033A
Other languages
English (en)
French (fr)
Other versions
CA2811033A1 (en
Inventor
Mary Theresa Didiuk
Robert Lee Dow
David Andrew Griffith
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.)
Pfizer Inc
Original Assignee
Pfizer 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 Pfizer Inc filed Critical Pfizer Inc
Publication of CA2811033A1 publication Critical patent/CA2811033A1/en
Application granted granted Critical
Publication of CA2811033C publication Critical patent/CA2811033C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic 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
    • C07D471/02—Heterocyclic 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
    • C07D471/10—Spiro-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic 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
    • A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/20—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2811033A 2010-09-30 2011-09-20 N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors Active CA2811033C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US38810210P 2010-09-30 2010-09-30
US61/388,102 2010-09-30
PCT/IB2011/054119 WO2012042433A1 (en) 2010-09-30 2011-09-20 N1-PYRAZOLOSPIROKETONE ACETYL-CoA CARBOXYLASE INHIBITORS

Publications (2)

Publication Number Publication Date
CA2811033A1 CA2811033A1 (en) 2012-04-05
CA2811033C true CA2811033C (en) 2015-10-20

Family

ID=44789556

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2811033A Active CA2811033C (en) 2010-09-30 2011-09-20 N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors

Country Status (15)

Country Link
US (8) US8859577B2 (enExample)
EP (1) EP2621493B1 (enExample)
JP (1) JP5824055B2 (enExample)
CA (1) CA2811033C (enExample)
CY (1) CY1118016T1 (enExample)
DK (1) DK2621493T3 (enExample)
ES (1) ES2602111T3 (enExample)
HR (1) HRP20161178T1 (enExample)
HU (1) HUE031616T2 (enExample)
LT (1) LT2621493T (enExample)
PL (1) PL2621493T3 (enExample)
PT (1) PT2621493T (enExample)
RS (1) RS55224B1 (enExample)
SI (1) SI2621493T1 (enExample)
WO (1) WO2012042433A1 (enExample)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040198483A1 (en) 2003-04-03 2004-10-07 Amaitis Lee M. System and method for betting on a subset of participants in an event
US9098883B2 (en) 2004-02-03 2015-08-04 Cantor Index, Llc Managing bets that select events and participants
US8636571B2 (en) 2004-02-03 2014-01-28 Cantor Index, Llc System and method for managing select five horseracing bets
WO2009144554A1 (en) 2008-05-28 2009-12-03 Pfizer, Inc. Pyrazolospiroketone acetyl-c0a carboxylase inhibitors
PT2499139E (pt) 2009-11-10 2014-02-10 Pfizer Inibidores de n1-pirazolospirocetona acetil-coa carboxilase
HRP20161178T1 (hr) 2010-09-30 2016-11-04 Pfizer Inc. N1-PIRAZOLOSPIROKETONSKI INHIBITORI ACETIL-CoA-KARBOKSILAZE
HUE025078T2 (en) 2010-10-29 2016-01-28 Pfizer N1 / N2-lactam-acetyl-CoA carboxylase inhibitors
PE20141187A1 (es) * 2011-04-22 2014-09-18 Pfizer Inhibidores sustituidos de aeitl-coa carboxilasa
US8905832B2 (en) 2012-01-30 2014-12-09 Cfph, Llc Event wagering with group and/or in run options
US11055967B2 (en) 2014-03-26 2021-07-06 Cfph, Llc Event wagering with group and/or in run options
US20170178994A1 (en) * 2015-12-21 2017-06-22 Intel Corporation Integrated circuit package support structures
KR102579876B1 (ko) 2016-02-22 2023-09-18 삼성전자주식회사 반도체 패키지
CN110536683A (zh) * 2017-04-18 2019-12-03 基恩菲特公司 包含PPAR激动剂如伊拉非诺和乙酰CoA羧化酶ACC抑制剂的组合
IL313710A (en) * 2017-11-21 2024-08-01 Pfizer Crystalline 2-amino-2-(hydroxymethyl)propane-1,3-diol salt of 4-(4-(1-isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4'-piperidine]-1'-carbonyl)-6-methoxypyridin-2-yl)benzoic acid
US10934279B2 (en) 2018-06-13 2021-03-02 Pfizer Inc. GLP-1 receptor agonists and uses thereof
BR112021003039A2 (pt) 2018-08-31 2021-05-18 Pfizer Inc. combinações para o tratamento de nash/nafld e doenças relacionadas
US12611401B2 (en) 2019-05-20 2026-04-28 Pfizer Inc. Combinations comprising benzodioxol as GLP-1R agonists for use in the treatment of NASH/NAFLD and related diseases
CN110183456A (zh) * 2019-07-11 2019-08-30 河南师范大学 一种2-芳基吲唑琥珀酰亚胺螺环化合物的合成方法
WO2021116874A1 (en) 2019-12-10 2021-06-17 Pfizer Inc. Solid forms of 2-((4-((s)-2-(5-chloropyridin-2-yl)-2-methylbenzo[d] [1,3]dioxol-4-yl)piperidin-1-yl)methyl)-1-(((s)-oxetan-2-yl)methyl)-1h-benzo[d] imidazole-6-carboxylic acid, 1,3-dihydroxy-2-(hydroxymethyl)propan-2-amine salt
AU2020417293A1 (en) 2020-01-03 2022-09-01 Berg Llc Polycyclic amides as UBE2K modulators for treating cancer
PE20231066A1 (es) 2020-02-07 2023-07-17 Gasherbrum Bio Inc Agonistas heterociclicos de glp-1
JP2021134211A (ja) * 2020-02-24 2021-09-13 ファイザー・インク Ｎａｆｌｄ／ｎａｓｈおよび関連疾患の処置のための組合せ
JP2022058085A (ja) 2020-02-24 2022-04-11 ファイザー・インク ジアシルグリセロールアシルトランスフェラーゼ２阻害剤とアセチル－ＣｏＡカルボキシラーゼ阻害剤との組合せ
IL296694A (en) 2020-03-27 2022-11-01 Pfizer Treatment of type 2 diabetes, obesity or excess weight using 2-[(4-{6-[(4-cyano-2-fluorobenzyl)oxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-[( 2s)-oxetan-2-ylmethyl]-1h-benzimidazole-6-carboxylic acid or its pharmaceutical salts
EP4143183B1 (en) 2020-04-29 2025-10-22 Gasherbrum Bio, Inc. Heterocyclic glp-1 agonists
CN117940422A (zh) 2021-08-31 2024-04-26 辉瑞大药厂 2-[(4-{6-[(4-氰基-2-氟芐基)氧基]吡啶-2-基}哌啶-1-基)甲基]-1-[(2s)-氧杂环丁烷-2-基甲基]-1h-苯并咪唑-6-羧酸，1,3-二羟基-2-(羟甲基)丙-2-胺盐的固体形式
JP2025509281A (ja) 2022-03-09 2025-04-11 ガシャーブラム・バイオ・インコーポレイテッド ヘテロ環式ｇｌｐ－１アゴニスト
EP4508047A1 (en) 2022-04-14 2025-02-19 Gasherbrum Bio, Inc. Heterocyclic glp-1 agonists
WO2023228023A1 (en) 2022-05-23 2023-11-30 Pfizer Inc. Treatment of type 2 diabetes or weight management control with 2-((4-((s)-2-(5-chloropyridin-2-yl)-2-methylbenzo[d][1,3]dioxol-4-yl)piperidin-1-yl)methyl)-1-(((s)-oxetan-2-yl)methyl)-1h-benzo[d]imidazole-6-carboxylic acid or a pharmaceutically salt thereof
CN120129681A (zh) 2022-10-18 2025-06-10 辉瑞大药厂 含Patatin样磷脂酶结构域的蛋白3（PNPLA3）调节剂
KR20250157491A (ko) 2022-12-15 2025-11-04 가셔브룸 바이오, 인크. Glp-1 효능제 활성을 갖는 화합물의 염 및 고체 형태
WO2025099561A1 (en) 2023-11-07 2025-05-15 Pfizer Inc. Oral controlled-release matrix formulations of 2-[(4-{6-[(4-cyano-2-fluorobenzyl)oxy]pyridin-2-yl}piperidin-1-yl)methyl]-1-[(2s)-oxetan-2-ylmethyl]-1h-benzimidazole-6-carboxylic acid or a pharmaceutically salt thereof
WO2025224648A1 (en) 2024-04-26 2025-10-30 Pfizer Inc. Oral compositions/formulations of 2-({4-[(2s)-2-(4-chloro-2-fluorophenyl)-2-methyl-1,3-benzodioxol-4-yl]piperidin-1-yl}methyl)-1-[(2s)-oxetan-2-ylmethyl]-1h-benzimidazole-6-carboxylic acid or a pharmaceutically salt thereof

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK0901786T3 (da) 1997-08-11 2007-10-08 Pfizer Prod Inc Faste farmaceutiske dispersioner med foröget biotilgængelighed
GEP20053710B (en) 2001-02-28 2005-12-26 Merck & Co Inc Acylated Piperidine Derivatives as Melanocortin-4 Receptor Agonists
NZ534582A (en) 2002-02-27 2006-03-31 Pfizer Prod Inc ACC inhibitors
US7105526B2 (en) 2002-06-28 2006-09-12 Banyu Pharmaceuticals Co., Ltd. Benzimidazole derivatives
JPWO2004092179A1 (ja) 2003-04-14 2006-07-06 日本曹達株式会社 スピロ誘導体、製造法および抗酸化薬
JP2005119987A (ja) 2003-10-15 2005-05-12 Ajinomoto Co Inc アシルスルホンアミド誘導体
WO2005113069A2 (en) 2004-05-14 2005-12-01 Research Development Foundation Use of circumin and analogues as inhibitors of acc2
EA010888B1 (ru) 2004-05-25 2008-12-30 Пфайзер Продактс, Инк. Тетраазабензо[е]азуленовые производные и их аналоги
PA8660701A1 (es) 2005-02-04 2006-09-22 Pfizer Prod Inc Agonistas de pyy y sus usos
KR20080036041A (ko) 2005-07-19 2008-04-24 머크 앤드 캄파니 인코포레이티드 아세틸 조효소 카복실라제(ａｃｃ) 억제제로서의스피로크로마논 유도체
WO2007013691A1 (ja) 2005-07-29 2007-02-01 Takeda Pharmaceutical Company Limited スピロ環化合物
DE102006016566B4 (de) 2005-09-22 2008-06-12 Beru Ag Zusammengesetzter Leiter, insbesondere für Glühkerzen für Dieselmotoren
US8071770B2 (en) 2005-11-18 2011-12-06 Merck Sharp & Dohme Corp. Spirohydantoin aryl CGRP receptor antagonists
CN101384568B (zh) 2006-02-15 2012-12-12 雅培制药有限公司 乙酰辅酶a羧化酶(acc)抑制剂及其在糖尿病、肥胖症和代谢综合征中的应用
EP2097420B1 (en) 2006-11-29 2012-04-04 Pfizer Products Inc. Spiroketone inhibitors of acetyl-coa carboxylase
US8138197B2 (en) * 2007-01-12 2012-03-20 Msd K.K. Spirochromanon derivatives
PE20081559A1 (es) 2007-01-12 2008-11-20 Merck & Co Inc DERIVADOS DE ESPIROCROMANONA SUSTITUIDOS COMO INHIBIDORES DE ACETIL CoA CARBOXILASA
JPWO2008102749A1 (ja) 2007-02-20 2010-05-27 武田薬品工業株式会社 複素環化合物
CA2683695C (en) 2007-04-12 2013-06-18 Pfizer Inc. 3-amido-pyrrolo[3,4-c]pyrazole-5(1h,4h,6h) carbaldehyde derivatives
US7981904B2 (en) 2008-03-20 2011-07-19 Takeda Pharmaceutical Company Limited Acetyl CoA carboxylase inhibitors
WO2009144554A1 (en) * 2008-05-28 2009-12-03 Pfizer, Inc. Pyrazolospiroketone acetyl-c0a carboxylase inhibitors
CA2724603A1 (en) 2008-05-28 2009-12-03 Pfizer Inc. Pyrazolospiroketone acetyl-coa carboxylase inhibitors
US8524730B2 (en) 2008-07-04 2013-09-03 Msd K.K. Spirochromanone carboxylic acids
WO2010008521A1 (en) 2008-07-14 2010-01-21 Cropsolution, Inc. Modulators of acetyl-coenzyme a carboxylase and methods of use thereof
PT2499139E (pt) 2009-11-10 2014-02-10 Pfizer Inibidores de n1-pirazolospirocetona acetil-coa carboxilase
JP2013510191A (ja) * 2009-11-10 2013-03-21 ファイザー・インク Ｎ−２ピラゾロスピロケトンアセチル−ＣｏＡカルボキシラーゼ阻害薬
HRP20161178T1 (hr) * 2010-09-30 2016-11-04 Pfizer Inc. N1-PIRAZOLOSPIROKETONSKI INHIBITORI ACETIL-CoA-KARBOKSILAZE
US20160034775A1 (en) 2014-08-02 2016-02-04 General Vault, LLC Methods and apparatus for bounded image data analysis and notification mechanism

Also Published As

Publication number Publication date
US10822335B2 (en) 2020-11-03
ES2602111T3 (es) 2017-02-17
US11673890B2 (en) 2023-06-13
US20150011470A1 (en) 2015-01-08
JP2013540119A (ja) 2013-10-31
SI2621493T1 (sl) 2016-10-28
RS55224B1 (sr) 2017-02-28
US20150376185A1 (en) 2015-12-31
DK2621493T3 (en) 2016-10-24
HRP20161178T1 (hr) 2016-11-04
EP2621493A1 (en) 2013-08-07
PT2621493T (pt) 2016-11-14
HUE031616T2 (hu) 2017-07-28
US9145416B2 (en) 2015-09-29
LT2621493T (lt) 2016-10-25
US9908883B2 (en) 2018-03-06
US20130190334A1 (en) 2013-07-25
US20180162858A1 (en) 2018-06-14
CA2811033A1 (en) 2012-04-05
CY1118016T1 (el) 2017-05-17
US8859577B2 (en) 2014-10-14
US20190218218A1 (en) 2019-07-18
US10294225B2 (en) 2019-05-21
US20210047325A1 (en) 2021-02-18
US20160347752A1 (en) 2016-12-01
JP5824055B2 (ja) 2015-11-25
WO2012042433A1 (en) 2012-04-05
PL2621493T3 (pl) 2017-01-31
EP2621493B1 (en) 2016-08-17
US20230322777A1 (en) 2023-10-12

Similar Documents

Publication Publication Date Title
US20230322777A1 (en) N1-Pyrazolospiroketone Acetyl-CoA Carboxylase Inhibitors
AU2010317501B2 (en) N1-pyrazolospiroketone acetyl-CoA carboxylase inhibitors
CA2815169C (en) N1/n2-lactam acetyl-coa carboxylase inhibitors
AU2012245996B2 (en) Pyrazolospiroketone derivatives for use as acetyl-CoA carboxylase inhibitors
US20120225900A1 (en) N2-pyrazolospiroketone acetyl-coa carboxylase inhibitors

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20130311

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: 20250811

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: 20250829