NO972930L - Fibronectin-adhesjonsinhibitorer - Google Patents

Fibronectin-adhesjonsinhibitorer

Info

Publication number
NO972930L
NO972930L NO972930A NO972930A NO972930L NO 972930 L NO972930 L NO 972930L NO 972930 A NO972930 A NO 972930A NO 972930 A NO972930 A NO 972930A NO 972930 L NO972930 L NO 972930L
Authority
NO
Norway
Prior art keywords
amino acid
acid selected
fibronectin
terminus
linker
Prior art date
Application number
NO972930A
Other languages
English (en)
Other versions
NO972930D0 (no
Inventor
Anand Swaroop Dutta
Original Assignee
Zeneca Ltd
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
Priority claimed from GBGB9426254.0A external-priority patent/GB9426254D0/en
Priority claimed from GBGB9505905.1A external-priority patent/GB9505905D0/en
Priority claimed from GBGB9513904.4A external-priority patent/GB9513904D0/en
Application filed by Zeneca Ltd filed Critical Zeneca Ltd
Publication of NO972930D0 publication Critical patent/NO972930D0/no
Publication of NO972930L publication Critical patent/NO972930L/no

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K14/00Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/78Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin or cold insoluble globulin [CIG]
    • 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
    • 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
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
    • 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
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pain & Pain Management (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biophysics (AREA)
  • Rheumatology (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biochemistry (AREA)
  • Immunology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Det beskrives cykliske peptider med formel (1) >-.AA1-AA2-AA3-AA'^ LINKER' (1) hvor AA1 er en L- eller ^-aminosyre valgt fra Ile ogLeu eller en aminosyreanalog derav, AA2 er en L-aminosyre valgl fra Lau eller en aminosyreanalog derav, AA3 er en L-aminosyre valgt fra Asp eller en aminosyreanalog cderav, som i sin sidekjede inneholderen karboksylgruppe; AA4 er en L-aminosyre valgt fra Val eller en aminosyreanalog derav, og; LINKER representerer en sammenkoblende del for å koble N-enden av AA1 til C- enden av AA4 under dannelse av et cyklisk peptid som inneholder en heterocyklisk ring som har 17 til 30 ledd. De cykliske peptidene inhiberer interaksjonen mellom VCAM-1 (Vascular Cell Adhesion Molecule-1) og fibronectin, med integrinet VLA-4 (Very Late Antigen 4) og har terapeutiske anvendelser, f eks. ved reumatoid artritt eller multippel sklerose.
NO972930A 1994-12-24 1997-06-23 Fibronectin-adhesjonsinhibitorer NO972930L (no)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB9426254.0A GB9426254D0 (en) 1994-12-24 1994-12-24 Chemical compounds
GBGB9505905.1A GB9505905D0 (en) 1995-03-23 1995-03-23 Methods
GBGB9513904.4A GB9513904D0 (en) 1995-07-07 1995-07-07 Chemical compounds
PCT/GB1995/002992 WO1996020216A1 (en) 1994-12-24 1995-12-21 Fibronectin adhesion inhibitors

Publications (2)

Publication Number Publication Date
NO972930D0 NO972930D0 (no) 1997-06-23
NO972930L true NO972930L (no) 1997-08-19

Family

ID=27267539

Family Applications (1)

Application Number Title Priority Date Filing Date
NO972930A NO972930L (no) 1994-12-24 1997-06-23 Fibronectin-adhesjonsinhibitorer

Country Status (18)

Country Link
US (1) US6034056A (no)
EP (1) EP0800535A1 (no)
JP (1) JP3248584B2 (no)
CN (1) CN1171118A (no)
AU (1) AU705717B2 (no)
BR (1) BR9510284A (no)
CA (1) CA2204793A1 (no)
CZ (1) CZ198497A3 (no)
GB (1) GB9524630D0 (no)
HU (1) HUT77120A (no)
IL (1) IL116512A0 (no)
MX (1) MX9704767A (no)
NO (1) NO972930L (no)
NZ (1) NZ297530A (no)
PL (1) PL320995A1 (no)
SK (1) SK81097A3 (no)
TR (1) TR199501656A2 (no)
WO (1) WO1996020216A1 (no)

Families Citing this family (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0842195A1 (en) * 1995-07-06 1998-05-20 Zeneca Limited Peptide inhibitors of fibronectine
GB9613112D0 (en) * 1996-06-21 1996-08-28 Zeneca Ltd Chemical compounds
DE19647381A1 (de) 1996-11-15 1998-05-20 Hoechst Ag Neue Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten
PL323130A1 (en) * 1996-11-15 1998-05-25 Hoechst Ag Application of heterocyclic compounds in production of a pharmaceutic agent, novel heterocyclic compounds and pharmaceutic agent as such
DE19653036A1 (de) * 1996-12-19 1998-06-25 Merck Patent Gmbh Cyclopeptidderivate
US6291511B1 (en) 1997-05-29 2001-09-18 Merck & Co., Inc. Biarylalkanoic acids as cell adhesion inhibitors
US6221888B1 (en) 1997-05-29 2001-04-24 Merck & Co., Inc. Sulfonamides as cell adhesion inhibitors
US6903075B1 (en) 1997-05-29 2005-06-07 Merck & Co., Inc. Heterocyclic amide compounds as cell adhesion inhibitors
DE19741235A1 (de) 1997-09-18 1999-03-25 Hoechst Marion Roussel De Gmbh Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
DE19741873A1 (de) * 1997-09-23 1999-03-25 Hoechst Marion Roussel De Gmbh Neue 5-Ring-Heterocyclen, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
US6069163A (en) * 1997-10-21 2000-05-30 Merck & Co., Inc. Azapeptide acids as cell adhesion inhibitors
US6020347A (en) * 1997-11-18 2000-02-01 Merck & Co., Inc. 4-substituted-4-piperidine carboxamide derivatives
DE19751251A1 (de) 1997-11-19 1999-05-20 Hoechst Marion Roussel De Gmbh Substituierte Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmezeutische Präparate
US6191171B1 (en) 1997-11-20 2001-02-20 Merck & Co., Inc. Para-aminomethylaryl carboxamide derivatives
US6090841A (en) * 1997-11-21 2000-07-18 Merck & Co., Inc. Substituted pyrrole derivatives as cell adhesion inhibitors
US6645939B1 (en) 1997-11-24 2003-11-11 Merck & Co., Inc. Substituted β-alanine derivatives as cell adhesion inhibitors
DE19821483A1 (de) 1998-05-14 1999-11-18 Hoechst Marion Roussel De Gmbh Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
DE19922462A1 (de) 1999-05-17 2000-11-23 Aventis Pharma Gmbh Spiro-imidazolidinderivate, ihre Herstellung ihre Verwendung und sie enthaltende pharmazeutische Präparate
EP1242118B1 (en) 1999-12-16 2009-11-11 Biogen Idec MA Inc. Methods of treating central nervous system ischemic or hemorrhagic injury using anti alpha4 integrin antagonists
NZ518886A (en) 1999-12-28 2004-02-27 Pfizer Prod Inc Non-peptidyl inhibitors of VLA-4 dependent cell binding useful in treating inflammatory, autoimmune, and respiratory diseases
GB0015923D0 (en) * 2000-06-30 2000-08-23 Astrazeneca Ab Methods
DE10111877A1 (de) 2001-03-10 2002-09-12 Aventis Pharma Gmbh Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
EP1423400B2 (en) * 2001-03-19 2013-05-22 President and Fellows of Harvard College Evolving new molecular function
DE10137595A1 (de) 2001-08-01 2003-02-13 Aventis Pharma Gmbh Neue Imidazolidinderivate, ihre Herstellung und ihre Verwendung
EP1423135A4 (en) * 2001-08-06 2006-06-07 Univ California PROCESS FOR INHIBITING THE ANGIOGENESIS
AR038136A1 (es) 2002-01-24 2004-12-29 Merck Frosst Canada Inc Cicloalcanindoles con sustitucion con fluor composiciones que contienen estos compuestos y metodos de tratamiento
US7247725B2 (en) 2002-10-30 2007-07-24 Merck & Co., Inc. Gamma-aminoamide modulators of chemokine receptor activity
CA2545248A1 (en) 2003-09-29 2005-04-14 The Regents Of The University Of California Methods for altering hematopoietic progenitor cell adhesion, differentiation, and migration
SE0302853D0 (sv) * 2003-10-29 2003-10-29 Astrazeneca Ab Chemical compounds
EP1734966B1 (en) 2004-04-13 2013-07-31 Incyte Corporation Piperazinylpiperidine derivatives as chemokine receptor antagonists
MEP1008A (xx) 2005-12-21 2010-02-10 Incyte Corp 3-aminociklopentankarboksamidi kao modulatori receptora hemokina
WO2007092471A2 (en) 2006-02-03 2007-08-16 The Regents Of The University Of California Methods for inhibition of lymphangiogenesis and tumor metastasis
CA2714335A1 (en) 2007-02-20 2008-08-28 Merrimack Pharmaceuticals, Inc. Methods of treating multiple sclerosis by administration of alpha-fetoprotein in combination with an integrin antagonist
FR2914304B1 (fr) * 2007-03-28 2012-11-16 Guerbet Sa Composes pour le diagnostic de maladies liees a l'expression de vcam.
JP2012502927A (ja) 2008-09-22 2012-02-02 メルク カナダ インコーポレイテッド Crth2受容体拮抗薬としてのインドール誘導体
WO2010051274A2 (en) * 2008-10-31 2010-05-06 Centocor Ortho Biotech Inc. Fibronectin type iii domain based scaffold compositions, methods and uses
WO2010053572A2 (en) 2008-11-07 2010-05-14 Massachusetts Institute Of Technology Aminoalcohol lipidoids and uses thereof
GEP20146064B (en) 2008-11-26 2014-03-25 Pfizer 3-minocyclopentanecarboxamides as chemokine receptor modulators
TW201041892A (en) 2009-02-09 2010-12-01 Supergen Inc Pyrrolopyrimidinyl Axl kinase inhibitors
MY152062A (en) 2009-02-24 2014-08-15 Merck Sharp & Dohme Indole derivatives as crth2 receptor antagonists
WO2011020874A1 (en) 2009-08-20 2011-02-24 Inserm (Institut National De La Sante Et De La Recherche Medicale) Vla-4 as a biomarker for prognosis and target for therapy in duchenne muscular dystrophy
US8853149B2 (en) 2010-03-19 2014-10-07 H. Lee Moffitt Cancer Center And Research Institute, Inc. Integrin interaction inhibitors for the treatment of cancer
WO2012051036A1 (en) 2010-10-11 2012-04-19 Merck Sharp & Dohme Corp. Quinazolinone-type compounds as crth2 antagonists
ES2635030T3 (es) 2010-12-23 2017-10-02 Merck Sharp & Dohme Corp. Quinoxalinas y aza-quinoxalinas como moduladores del receptor CRTH2
US9428845B1 (en) 2010-12-28 2016-08-30 Warp Drive Bio, Inc. Identifying new therapeutic agents
CA2831392C (en) 2011-03-28 2020-04-28 Massachusetts Institute Of Technology Conjugated lipomers and uses thereof
WO2012151137A1 (en) 2011-05-04 2012-11-08 Merck Sharp & Dohme Corp. Amino-pyridine-containing spleen tyrosine kinase (syk) inhibitors
ES2613644T3 (es) 2011-06-17 2017-05-25 Merck Sharp & Dohme Corp. Tetrahidroquinolinas condensadas con cicloalquilo como moduladores del receptor CRTH2
US8987456B2 (en) 2011-10-05 2015-03-24 Merck Sharp & Dohme Corp. 3-pyridyl carboxamide-containing spleen tyrosine kinase (SYK) inhibitors
EA032088B1 (ru) 2011-10-27 2019-04-30 Массачусетс Инститьют Оф Текнолоджи Аминокислотные производные, функционализованные на n-конце, способные образовывать микросферы, инкапсулирующие лекарственное средство
CA2884870C (en) 2012-08-13 2022-03-29 Massachusetts Institute Of Technology Amine-containing lipidoids and uses thereof
US10011635B2 (en) 2013-09-27 2018-07-03 H. Lee Moffitt Cancer Center And Research Institute, Inc. Cyclic peptide conjugates and methods of use
GB201400292D0 (en) 2014-01-08 2014-02-26 Haemostatix Ltd Peptide dendrimers and agents
CN106659731A (zh) 2014-05-30 2017-05-10 夏尔人类遗传性治疗公司 用于递送核酸的可生物降解脂质
MX2017000143A (es) 2014-06-24 2017-05-01 Shire Human Genetic Therapies Composiciones enriquecidas estereoquimicamente para administracion de acidos nucleicos.
WO2016004202A1 (en) 2014-07-02 2016-01-07 Massachusetts Institute Of Technology Polyamine-fatty acid derived lipidoids and uses thereof
EP3247378B8 (en) 2015-01-09 2023-08-23 Revolution Medicines, Inc. Macrocyclic compounds that participate in cooperative binding and medical uses thereof
TW201629069A (zh) * 2015-01-09 2016-08-16 霍普驅動生物科技股份有限公司 參與協同結合之化合物及其用途
HUE062274T2 (hu) 2015-06-19 2023-10-28 Massachusetts Inst Technology Alkenil-szubsztituált 2,5-piperazindionok és alkalmazásuk hatóanyag alanyba vagy sejtbe történõ célbajuttatására szolgáló készítményekben
CA3000822A1 (en) 2015-10-01 2017-04-06 Warp Drive Bio, Inc. Methods and reagents for analyzing protein-protein interfaces
WO2017079820A1 (en) * 2015-11-11 2017-05-18 Encycle Therapeutics, Inc. CYCLIC PEPTIDES TARGETING α4β7 INTEGRIN
EP3442599B1 (en) 2016-04-12 2022-03-30 Warp Drive Bio, Inc. Compositions and methods for the production of compounds
CA3042231A1 (en) 2016-10-28 2018-05-03 Ginkgo Bioworks, Inc. Compositions and methods for the production of compounds
CA3042576A1 (en) * 2016-11-11 2018-05-17 Encycle Therapeutics, Inc. Cyclic peptides multimers targeting .alpha.4.beta.7 integrin
WO2018140510A1 (en) 2017-01-25 2018-08-02 Biogen Ma Inc. Compositions and methods for treatment of stroke and other cns disorders
CA3062385A1 (en) 2017-05-10 2018-11-15 Encycle Therapeutics, Inc. Homodetic cyclic peptides targeting a4s7 1ntegrin
JP2022517610A (ja) 2019-01-10 2022-03-09 シーエスピーシー ゾンチー ファーマシューティカル テクノロジー(シージアチュアン)カンパニー,リミテッド 複素環化合物塩およびその使用
KR20220109407A (ko) 2019-11-04 2022-08-04 레볼루션 메디슨즈, 인크. Ras 억제제
AU2020379734A1 (en) 2019-11-04 2022-05-05 Revolution Medicines, Inc. Ras inhibitors
WO2021091967A1 (en) 2019-11-04 2021-05-14 Revolution Medicines, Inc. Ras inhibitors
US11690915B2 (en) 2020-09-15 2023-07-04 Revolution Medicines, Inc. Ras inhibitors
EP4284947A1 (en) 2021-01-29 2023-12-06 Institut National de la Santé et de la Recherche Médicale (INSERM) Methods of assessing the risk of developing progressive multifocal leukoencephalopathy in patients treated with vla-4 antagonists

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZW6189A1 (en) * 1988-05-09 1990-05-09 Smithkline Beckman Corp Anti-aggregatory peptides
NZ235563A (en) * 1989-10-13 1993-04-28 Merck & Co Inc Fibrinogen receptor antagonist and pharmaceutical composition
US5192746A (en) * 1990-07-09 1993-03-09 Tanabe Seiyaku Co., Ltd. Cyclic cell adhesion modulation compounds
IL102646A (en) * 1992-07-26 1996-05-14 Yeda Res & Dev Non-peptidic surrogates of the ldv sequence and pharmaceutical compositions comprising them
JPH08505628A (ja) * 1993-01-08 1996-06-18 田辺製薬株式会社 ペプチド型細胞接着阻害薬
US5981478A (en) * 1993-11-24 1999-11-09 La Jolla Cancer Research Foundation Integrin-binding peptides
EP0767674A4 (en) * 1994-06-29 1999-06-16 Texas Biotechnology Corp METHOD FOR INHIBITING THE BINDING OF INTEGRIN ALPHA 4 BETA 1 TO VCAM-1 OR FIBRONECTIN
US5811391A (en) * 1994-08-25 1998-09-22 Cytel Corporation Cyclic CS-1 peptidomimetics, compositions and methods of using same
EP0741948B1 (en) * 1994-11-02 2000-05-10 Koninklijke Philips Electronics N.V. Waveform generation

Also Published As

Publication number Publication date
BR9510284A (pt) 1998-01-06
MX9704767A (es) 1997-10-31
CA2204793A1 (en) 1996-07-04
CZ198497A3 (en) 1997-10-15
NZ297530A (en) 2000-02-28
NO972930D0 (no) 1997-06-23
JP3248584B2 (ja) 2002-01-21
WO1996020216A1 (en) 1996-07-04
AU705717B2 (en) 1999-05-27
CN1171118A (zh) 1998-01-21
US6034056A (en) 2000-03-07
TR199501656A2 (tr) 1996-07-21
JPH10508315A (ja) 1998-08-18
SK81097A3 (en) 1997-12-10
HUT77120A (hu) 1998-03-02
EP0800535A1 (en) 1997-10-15
PL320995A1 (en) 1997-11-24
AU4269896A (en) 1996-07-19
GB9524630D0 (en) 1996-01-31
IL116512A0 (en) 1996-07-23

Similar Documents

Publication Publication Date Title
NO972930L (no) Fibronectin-adhesjonsinhibitorer
Yaron et al. Proline-dependent structural and biological properties of peptides and proteins
ATE165836T1 (de) Peptide als arzneimittel
NZ332778A (en) Cyclic peptides that are cell adhesion inhibiting compounds that inhibit the interaction of vascular cell adhesion molecule-1 and fibronectin with integrin very late antigen and mucosal addressin cell adhesion molecule-1
FI102379B1 (fi) Uretaanisuojattuja aminohappo-N-karboksianhydridejä
Witkop Chemical Cleavage of Proteins: Selective fragmentations and modifications reveal structure.
Katsoyannis The synthesis of the insulin chains and their combination to biologically active material
DE69009476T2 (de) Hemmung des reaktionswegs für die n-ende-regel in lebenden zellen.
ABEL et al. Structural differences in the hinge region of human gamma A myeloma proteins of different subclasses
ATE205855T1 (de) Gegen bakterien, mycota und viren wirksame vertebraten proteine und dessen kosmetische zubereitungen
Franciskovich et al. A systematic evaluation of the inhibition of HIV-1 protease by its C-and N-terminal peptides
KR0154528B1 (ko) 항응고성 펩티드
US5192747A (en) Anticoagulant peptides
ATE140234T1 (de) Neue inhibitorische peptide
ATE245168T1 (de) Peptide, die anti-zellanhaftungsaktivität aufweisen
DK0667781T3 (da) Peptidbaserede diagnostiske og terapeutiske midler til spondylarthropatier
Moroder et al. Studies on cytochrome c. Part I. Synthesis of the protected hexadecapeptide (sequence 1–16) of Baker's Yeast iso‐1‐cytochrome c
Ten Kortenaar et al. Semisynthesis of horse heart cytochrome c analogues from two or three fragments.
WO1993000108A1 (en) Novel inhibitors of platelet aggregation
Gaudron et al. NAcSDKP analogues resistant to angiotensin-converting enzyme
Fraenkel-Conrat The chemistry of proteins and peptides
Nozaki et al. Synthetic studies on troponin I active site. Preparation of a pentadecapeptide with inhibitory activity toward actomyosin adenosine triphosphatase
ATE85077T1 (de) Enzym zur alpha-amidierung von c-termini und verfahren zu dessen herstellung.
NO993684L (no) Peptider som omfatter et T-celle-epitop spesifikt til kollagen-II
ATE46173T1 (de) Pharmakologisch aktive peptide.

Legal Events

Date Code Title Description
FC2A Withdrawal, rejection or dismissal of laid open patent application