TWI736529B - 氟化之四氫啶基壬酸衍生物及其用途 - Google Patents

氟化之四氫啶基壬酸衍生物及其用途 Download PDF

Info

Publication number
TWI736529B
TWI736529B TW105104964A TW105104964A TWI736529B TW I736529 B TWI736529 B TW I736529B TW 105104964 A TW105104964 A TW 105104964A TW 105104964 A TW105104964 A TW 105104964A TW I736529 B TWI736529 B TW I736529B
Authority
TW
Taiwan
Prior art keywords
fold
compound
present
disease
fibrosis
Prior art date
Application number
TW105104964A
Other languages
English (en)
Chinese (zh)
Other versions
TW201643161A (zh
Inventor
班 艾斯克
古谷建
Original Assignee
美商賽氟洛生命科學公司
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 美商賽氟洛生命科學公司 filed Critical 美商賽氟洛生命科學公司
Publication of TW201643161A publication Critical patent/TW201643161A/zh
Application granted granted Critical
Publication of TWI736529B publication Critical patent/TWI736529B/zh

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
    • A61K31/435Heterocyclic 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
    • A61K31/4375Heterocyclic 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 six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • 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
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/70One oxygen atom
    • 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
    • C07D401/06Heterocyclic 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 linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
TW105104964A 2015-02-19 2016-02-19 氟化之四氫啶基壬酸衍生物及其用途 TWI736529B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201562118303P 2015-02-19 2015-02-19
US62/118,303 2015-02-19

Publications (2)

Publication Number Publication Date
TW201643161A TW201643161A (zh) 2016-12-16
TWI736529B true TWI736529B (zh) 2021-08-21

Family

ID=56689184

Family Applications (1)

Application Number Title Priority Date Filing Date
TW105104964A TWI736529B (zh) 2015-02-19 2016-02-19 氟化之四氫啶基壬酸衍生物及其用途

Country Status (13)

Country Link
US (5) US9790222B2 (https=)
EP (2) EP3925959A1 (https=)
JP (2) JP2018510139A (https=)
KR (1) KR102647026B1 (https=)
CN (2) CN114805342A (https=)
AU (1) AU2016219906B2 (https=)
BR (1) BR112017017888A2 (https=)
CA (1) CA2976634C (https=)
ES (1) ES2892954T3 (https=)
IL (1) IL253873A0 (https=)
RU (1) RU2017132433A (https=)
TW (1) TWI736529B (https=)
WO (1) WO2016134223A2 (https=)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8901144B2 (en) * 2013-02-07 2014-12-02 Scifluor Life Sciences, Llc Fluorinated 3-(2-oxo-3-(3-arylpropyl)imidazolidin-1-yl)-3-arylpropanoic acid derivatives
PT2953948T (pt) 2013-02-07 2017-12-12 Scifluor Life Sciences Inc Antagonistas de integrina fluorada
GB201305668D0 (en) 2013-03-28 2013-05-15 Glaxosmithkline Ip Dev Ltd Avs6 Integrin Antagonists
GB201417018D0 (en) 2014-09-26 2014-11-12 Glaxosmithkline Ip Dev Ltd Novel compounds
GB201417094D0 (en) 2014-09-26 2014-11-12 Glaxosmithkline Ip Dev Ltd Novel compounds
GB201417011D0 (en) 2014-09-26 2014-11-12 Glaxosmithkline Ip Dev Ltd Novel compounds
GB201417002D0 (en) 2014-09-26 2014-11-12 Glaxosmithkline Ip Dev Ltd Novel compound
US9790222B2 (en) * 2015-02-19 2017-10-17 Scifluor Life Sciences, Inc. Fluorinated tetrahydronaphthyridinyl nonanoic acid derivatives and uses thereof
WO2016154369A1 (en) * 2015-03-26 2016-09-29 Merck Sharp & Dohme Corp. Composition and methods for treating chronic kidney disease
BR112017023432A2 (pt) * 2015-04-30 2018-07-24 Scifluor Life Sciences Inc Derivados de ácido propiônico tetra- hidronaftiridinila e usos do mesmo
GB201604680D0 (en) 2016-03-21 2016-05-04 Glaxosmithkline Ip Dev Ltd Chemical Compounds
US10118929B2 (en) 2016-04-27 2018-11-06 Scifluor Life Sciences, Inc. Nonanoic and decanoic acid derivatives and uses thereof
EP3509590A4 (en) 2016-09-07 2020-12-02 Pliant Therapeutics, Inc. N-ACYL AMINO ACID COMPOUNDS AND METHODS OF USE
HRP20210228T1 (hr) 2016-11-08 2021-03-19 Bristol-Myers Squibb Company Amidi pirola kao inhibitori alfa v integrina
ES2984394T3 (es) * 2016-11-08 2024-10-29 Bristol Myers Squibb Co Compuestos mono y espirocíclicos que contienen ciclobutano y azetidina como inhibidores de la integrina alfa v
BR112019009245A2 (pt) 2016-11-08 2019-07-16 Bristol-Myers Squibb Company azol amidas e aminas como inibidores de alfav integrina
WO2018089357A1 (en) 2016-11-08 2018-05-17 Bristol-Myers Squibb Company INDAZOLE DERIVATIVES AS αV INTEGRIN ANTAGONISTS
AU2017359023B2 (en) 2016-11-08 2021-12-09 Bristol-Myers Squibb Company 3-substituted propionic acids as alpha v integrin inhibitors
MA52117A (fr) 2017-02-28 2022-04-06 Morphic Therapeutic Inc Inhibiteurs de l'intégrine (alpha-v) (bêta-6)
MX394210B (es) 2017-02-28 2025-03-04 Morphic Therapeutic Inc INHIBIDORES DE INTEGRINA AVß6.
WO2018183795A1 (en) * 2017-03-30 2018-10-04 Scifluor Life Sciences, Inc. Method of making tetrahydronaphthyridinyl nonanoic acid compounds
KR102700471B1 (ko) 2017-11-07 2024-08-28 브리스톨-마이어스 스큅 컴퍼니 알파 v 인테그린 억제제로서의 피롤로피라진 유도체
SG11202009734VA (en) * 2018-04-27 2020-11-27 Arrowhead Pharmaceuticals Inc Integrin targeting ligands and uses thereof
WO2020047239A1 (en) 2018-08-29 2020-03-05 Morphic Therapeutic, Inc. INHIBITING αV β6 INTEGRIN
SI3844162T1 (sl) * 2018-08-29 2025-06-30 Morphic Therapeutic, Inc. Zaviralci integrina alfa v beta6
WO2020047208A1 (en) 2018-08-29 2020-03-05 Morphic Therapeutic, Inc. Inhibitors of (alpha-v)(beta-6) integrin
CN115989235A (zh) * 2020-05-07 2023-04-18 普利安特治疗公司 使用氨基酸化合物治疗呼吸系统疾病的方法
WO2021231581A1 (en) 2020-05-12 2021-11-18 Scifluor Life Sciences, Inc. METHODS OF TREATING OR PREVENTING VIRAL INFECTION WITH FLUORINATED α V INTEGRIN ANTAGONISTS
US20230398061A1 (en) * 2020-10-20 2023-12-14 The Board Of Trustees Of The Leland Stanford Junior University Injectable hydrogels for adoptive cell therapy

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6410526B1 (en) * 1999-06-02 2002-06-25 Merck & Co., Inc. αv integrin receptor antagonists
WO2014124302A1 (en) * 2013-02-07 2014-08-14 Scifluor Life Sciences, Llc Fluorinated integrin antagonists

Family Cites Families (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4927266A (en) 1987-03-30 1990-05-22 Anritsu Corporation Optical signal generating apparatus and optical power meter calibrating system using the same
CA1318254C (en) 1988-01-06 1993-05-25 Munehiro Tomikawa Inhibitory agent of hepatic fibrosis containing pantethine
ES2104938T3 (es) 1991-04-01 1997-10-16 Univ Duke Metodo de inhibir la fibrosis.
US5501969A (en) 1994-03-08 1996-03-26 Human Genome Sciences, Inc. Human osteoclast-derived cathepsin
JP3818322B2 (ja) 1994-04-28 2006-09-06 敏一 中村 コラーゲン分解促進剤
US6544767B1 (en) 1994-10-27 2003-04-08 Axys Pharmaceuticals, Inc. Cathespin O2 protease
US5736357A (en) 1994-10-27 1998-04-07 Arris Pharmaceutical Cathespin O protease
US5645839A (en) 1995-06-07 1997-07-08 Trustees Of Boston University Combined use of angiotensin inhibitors and nitric oxide stimulators to treat fibrosis
US6664227B1 (en) 1996-03-01 2003-12-16 Genetics Institute, Llc Treatment of fibrosis by antagonism of IL-13 and IL-13 receptor chains
US6211184B1 (en) 1996-08-29 2001-04-03 Merck & Co., Inc. Integrin antagonists
WO1998008528A1 (en) 1996-08-30 1998-03-05 Biomeasure Incorporated Method of inhibiting fibrosis with a somatostatin agonist
CA2315370A1 (en) 1997-12-17 1999-06-24 Merck & Co., Inc. Integrin receptor antagonists
US6017926A (en) 1997-12-17 2000-01-25 Merck & Co., Inc. Integrin receptor antagonists
EA003095B1 (ru) * 1997-12-17 2002-12-26 Мерк Энд Ко., Инк. Антагонисты рецепторов интегринов
CN1284955A (zh) 1997-12-17 2001-02-21 麦克公司 整联蛋白受体拮抗剂
US6066648A (en) 1997-12-17 2000-05-23 Merck & Co., Inc. Integrin receptor antagonists
US6048861A (en) 1997-12-17 2000-04-11 Merck & Co., Inc. Integrin receptor antagonists
KR20010033248A (ko) 1997-12-17 2001-04-25 폴락 돈나 엘. 인테그린 수용체 길항제
US6117445A (en) 1998-01-28 2000-09-12 Link Technology Inc. Methods for the prevention and treatment of fibrosis and sclerosis
US6420396B1 (en) * 1998-12-16 2002-07-16 Beiersdorf Ag Biphenyl and biphenyl-analogous compounds as integrin antagonists
US6677360B2 (en) 1998-12-16 2004-01-13 Bayer Aktiengesellschaft Biphenyl and biphenyl-analogous compounds as integrin antagonists
US6291503B1 (en) * 1999-01-15 2001-09-18 Bayer Aktiengesellschaft β-phenylalanine derivatives as integrin antagonists
US6407241B1 (en) 1999-11-08 2002-06-18 Merck & Co., Inc. Process and intermediates for the preparation of imidazolidinone αv integrin antagonists
US6455539B2 (en) * 1999-12-23 2002-09-24 Celltech R&D Limited Squaric acid derivates
CA2397194C (en) 2000-01-20 2011-05-17 Mark E. Duggan Alpha v integrin receptor antagonists
CA2397665A1 (en) 2000-01-24 2001-07-26 Merck & Co., Inc. Alpha v integrin receptor antagonists
CN1366461A (zh) 2000-02-22 2002-08-28 三得利株式会社 含有胃促胰酶抑制剂作为有效成分的预防或治疗纤维变性的药物
GB0011817D0 (en) * 2000-05-16 2000-07-05 Pharmacia & Upjohn Spa Antagonists of integrin receptors
AU7793501A (en) 2000-07-26 2002-02-05 Merck & Co Inc Alpha v integrin receptor antagonists
WO2002022616A2 (en) 2000-09-14 2002-03-21 Merck & Co., Inc. Alpha v integrin receptor antagonists
WO2002022615A1 (en) 2000-09-14 2002-03-21 Merck & Co., Inc. Alpha v integrin receptor antagonists
EP1322311A1 (en) * 2000-09-18 2003-07-02 Merck & Co., Inc. Treatment of inflammation with a combination of a cyclooxygenase-2 inhibitor and an integrin alpha-v antagonist
EP1444231A4 (en) 2001-11-06 2005-11-09 Merck & Co Inc AMINO SALT OF AN INTEGRIN RECEPTOR ANTAGONIST
US20040053968A1 (en) 2001-12-28 2004-03-18 Hartman George D. Methods and compositions for treating peridontal disease
EP1551401A4 (en) 2002-09-20 2006-03-22 Merck & Co Inc MANNITOL FORMULATION FOR AN INTEGRIN RECEPTOR ANTAGONIST
EP1592421A1 (en) 2002-12-20 2005-11-09 Pharmacia Corporation Heteroarylalkanoic acids as integrin receptor antagonists
ATE399542T1 (de) 2003-10-01 2008-07-15 Merck Patent Gmbh Alfavbeta3 und alfavbeta6 integrin antagonisten als antifibrotische mittel
CN102026671B (zh) * 2008-03-14 2014-09-03 Visen医药公司 整联蛋白靶向试剂及使用其的体内和体外成像方法
WO2011060395A1 (en) 2009-11-16 2011-05-19 Schering Corporation Cyclic ureas useful as hiv inhibitors
US8969349B2 (en) 2010-05-26 2015-03-03 Sunovion Pharmaceuticals Inc. Substituted quinoxalines and quinoxalinones as PDE-10 inhibitors
KR102165421B1 (ko) 2011-05-09 2020-10-14 알레그로 파마슈티칼스, 인코포레이티드. 인테그린 수용체 길항물질 및 이의 사용 방법
CN103764118A (zh) 2011-06-28 2014-04-30 拜尔健康护理有限责任公司 含有索拉非尼的局部眼用药用组合物
US8901144B2 (en) 2013-02-07 2014-12-02 Scifluor Life Sciences, Llc Fluorinated 3-(2-oxo-3-(3-arylpropyl)imidazolidin-1-yl)-3-arylpropanoic acid derivatives
US9790222B2 (en) * 2015-02-19 2017-10-17 Scifluor Life Sciences, Inc. Fluorinated tetrahydronaphthyridinyl nonanoic acid derivatives and uses thereof
BR112017023432A2 (pt) 2015-04-30 2018-07-24 Scifluor Life Sciences Inc Derivados de ácido propiônico tetra- hidronaftiridinila e usos do mesmo
WO2018183795A1 (en) * 2017-03-30 2018-10-04 Scifluor Life Sciences, Inc. Method of making tetrahydronaphthyridinyl nonanoic acid compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6410526B1 (en) * 1999-06-02 2002-06-25 Merck & Co., Inc. αv integrin receptor antagonists
WO2014124302A1 (en) * 2013-02-07 2014-08-14 Scifluor Life Sciences, Llc Fluorinated integrin antagonists

Also Published As

Publication number Publication date
ES2892954T3 (es) 2022-02-07
AU2016219906A1 (en) 2017-09-07
WO2016134223A3 (en) 2016-10-20
CN114805342A (zh) 2022-07-29
WO2016134223A2 (en) 2016-08-25
IL253873A0 (en) 2017-10-31
JP2018510139A (ja) 2018-04-12
RU2017132433A3 (https=) 2019-03-25
JP7191299B2 (ja) 2022-12-19
KR20170117578A (ko) 2017-10-23
EP3259271A2 (en) 2017-12-27
US20240092775A1 (en) 2024-03-21
US20210277000A1 (en) 2021-09-09
JP2021008511A (ja) 2021-01-28
CA2976634C (en) 2023-10-17
US20160244447A1 (en) 2016-08-25
KR102647026B1 (ko) 2024-03-12
US12286432B2 (en) 2025-04-29
TW201643161A (zh) 2016-12-16
US11685738B2 (en) 2023-06-27
AU2016219906B2 (en) 2020-10-01
EP3925959A1 (en) 2021-12-22
US9790222B2 (en) 2017-10-17
CA2976634A1 (en) 2016-08-25
RU2017132433A (ru) 2019-03-19
US20170369490A1 (en) 2017-12-28
US10301307B2 (en) 2019-05-28
CN107531699A (zh) 2018-01-02
BR112017017888A2 (pt) 2018-04-10
EP3259271B1 (en) 2021-05-05
US20190225609A1 (en) 2019-07-25
EP3259271A4 (en) 2018-07-11

Similar Documents

Publication Publication Date Title
TWI736529B (zh) 氟化之四氫啶基壬酸衍生物及其用途
CN105246889B (zh) 氟化整联蛋白拮抗剂
WO2018183795A1 (en) Method of making tetrahydronaphthyridinyl nonanoic acid compounds
US10118929B2 (en) Nonanoic and decanoic acid derivatives and uses thereof
HK40066388A (en) Fluorinated derivatives of 3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid and uses thereof
HK1243061A1 (en) Fluorinated tetrahydronaphthyridinyl nonanoic acid derivatives and uses thereof
HK1241361B (en) Fluorinated derivatives of 3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid and uses thereof
HK1248677B (en) Fluorinated integrin antagonists
HK1217696B (en) Fluorinated integrin antagonists

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees