KR20120092617A - 단백질 티로신 키나제 2 저해제로서의 피리미딘 유도체 - Google Patents

단백질 티로신 키나제 2 저해제로서의 피리미딘 유도체 Download PDF

Info

Publication number
KR20120092617A
KR20120092617A KR1020127011321A KR20127011321A KR20120092617A KR 20120092617 A KR20120092617 A KR 20120092617A KR 1020127011321 A KR1020127011321 A KR 1020127011321A KR 20127011321 A KR20127011321 A KR 20127011321A KR 20120092617 A KR20120092617 A KR 20120092617A
Authority
KR
South Korea
Prior art keywords
methoxy
ylamino
benzamide
membered
trifluoromethylpyrimidin
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.)
Withdrawn
Application number
KR1020127011321A
Other languages
English (en)
Korean (ko)
Inventor
하인즈 스타트뮐러
아이오아니스 사포운치스
Original Assignee
베링거 인겔하임 인터내셔날 게엠베하
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=43048878&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=KR20120092617(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by 베링거 인겔하임 인터내셔날 게엠베하 filed Critical 베링거 인겔하임 인터내셔날 게엠베하
Publication of KR20120092617A publication Critical patent/KR20120092617A/ko
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72Quinazolines; Hydrogenated quinazolines
    • C07D239/78Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
    • C07D239/84Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • 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
    • 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
    • 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
    • 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
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D401/12Heterocyclic 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 chain containing hetero atoms as chain links
    • 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
    • C07D403/12Heterocyclic 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 chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Oncology (AREA)
  • Rheumatology (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
KR1020127011321A 2009-10-02 2010-10-01 단백질 티로신 키나제 2 저해제로서의 피리미딘 유도체 Withdrawn KR20120092617A (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP09172026.8 2009-10-02
EP09172026 2009-10-02
EP10172460.7 2010-08-11
EP10172460 2010-08-11

Publications (1)

Publication Number Publication Date
KR20120092617A true KR20120092617A (ko) 2012-08-21

Family

ID=43048878

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020127011321A Withdrawn KR20120092617A (ko) 2009-10-02 2010-10-01 단백질 티로신 키나제 2 저해제로서의 피리미딘 유도체

Country Status (25)

Country Link
US (1) US8466155B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP2483249B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JP5702390B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
KR (1) KR20120092617A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CN (1) CN102695700A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AP (1) AP2012006166A0 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AR (1) AR078513A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU2010302648A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
BR (1) BR112012007300A2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA2775418A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CL (1) CL2012000825A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EA (1) EA201200552A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EC (1) ECSP12011830A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IL (1) IL218543A0 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IN (1) IN2012DN02714A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
MA (1) MA33606B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
MX (1) MX2012003101A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NZ (1) NZ598614A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PE (1) PE20121431A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PH (1) PH12012500527A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
TN (1) TN2012000142A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
TW (1) TW201124386A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
UY (1) UY32916A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO2011039344A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ZA (1) ZA201201703B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120244141A1 (en) 2010-09-28 2012-09-27 Boehringer Ingelheim International Gmbh Stratification of cancer patients for susceptibility to therapy with PTK2 inhibitors
US8754114B2 (en) 2010-12-22 2014-06-17 Incyte Corporation Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3
WO2012110774A1 (en) 2011-02-17 2012-08-23 Cancer Therapeutics Crc Pty Limited Selective fak inhibitors
JP5937111B2 (ja) 2011-02-17 2016-06-22 カンサー・セラピューティクス・シーアールシー・プロプライエタリー・リミテッドCancer Therapeutics Crc Pty Limited Fak阻害剤
EP2788378A4 (en) * 2011-12-09 2015-09-09 Oncomed Pharm Inc ASSOCIATION THERAPY FOR THE TREATMENT OF CANCER
EP2832734A4 (en) * 2012-03-28 2015-08-26 Takeda Pharmaceutical HETEROCYCLIC COMPOUND
EP2861595B9 (en) 2012-06-13 2017-06-21 Incyte Holdings Corporation Substituted tricyclic compounds as fgfr inhibitors
US9388185B2 (en) 2012-08-10 2016-07-12 Incyte Holdings Corporation Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors
US9266892B2 (en) 2012-12-19 2016-02-23 Incyte Holdings Corporation Fused pyrazoles as FGFR inhibitors
TWI715901B (zh) 2013-04-19 2021-01-11 美商英塞特控股公司 作為fgfr抑制劑之雙環雜環
WO2014190207A1 (en) * 2013-05-22 2014-11-27 The Regents Of The University Of California Aurora kinase inhibitors
US10851105B2 (en) 2014-10-22 2020-12-01 Incyte Corporation Bicyclic heterocycles as FGFR4 inhibitors
MA41551A (fr) 2015-02-20 2017-12-26 Incyte Corp Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4
WO2016134294A1 (en) 2015-02-20 2016-08-25 Incyte Corporation Bicyclic heterocycles as fgfr4 inhibitors
MX388991B (es) 2015-02-20 2025-03-20 Incyte Corp Heterociclos biciclicos como inhibidores de receptores del factor de crecimiento fibroblastico (fgfr)
AR111960A1 (es) 2017-05-26 2019-09-04 Incyte Corp Formas cristalinas de un inhibidor de fgfr y procesos para su preparación
EP3788047B1 (en) 2018-05-04 2024-09-04 Incyte Corporation Solid forms of an fgfr inhibitor and processes for preparing the same
MA52493A (fr) 2018-05-04 2021-03-10 Incyte Corp Sels d'un inhibiteur de fgfr
WO2020185532A1 (en) 2019-03-08 2020-09-17 Incyte Corporation Methods of treating cancer with an fgfr inhibitor
WO2021007269A1 (en) 2019-07-09 2021-01-14 Incyte Corporation Bicyclic heterocycles as fgfr inhibitors
US12122767B2 (en) 2019-10-01 2024-10-22 Incyte Corporation Bicyclic heterocycles as FGFR inhibitors
WO2021076602A1 (en) 2019-10-14 2021-04-22 Incyte Corporation Bicyclic heterocycles as fgfr inhibitors
WO2021076728A1 (en) 2019-10-16 2021-04-22 Incyte Corporation Bicyclic heterocycles as fgfr inhibitors
CR20220285A (es) 2019-12-04 2022-10-27 Incyte Corp Derivados de un inhibidor de fgfr
US11897891B2 (en) 2019-12-04 2024-02-13 Incyte Corporation Tricyclic heterocycles as FGFR inhibitors
US12012409B2 (en) 2020-01-15 2024-06-18 Incyte Corporation Bicyclic heterocycles as FGFR inhibitors
WO2022221170A1 (en) 2021-04-12 2022-10-20 Incyte Corporation Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent
TW202313611A (zh) 2021-06-09 2023-04-01 美商英塞特公司 作為fgfr抑制劑之三環雜環
WO2023107705A1 (en) 2021-12-10 2023-06-15 Incyte Corporation Bicyclic amines as cdk12 inhibitors

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0004887D0 (en) * 2000-03-01 2000-04-19 Astrazeneca Uk Ltd Chemical compounds
KR100874791B1 (ko) 2001-05-29 2008-12-18 바이엘 쉐링 파마 악티엔게젤샤프트 Cdk-억제 피리미딘, 그의 제조방법 및 약제로서의 용도
WO2003032997A1 (de) 2001-10-17 2003-04-24 Boehringer Ingelheim Pharma Gmbh & Co. Kg Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung
JP2005526765A (ja) * 2002-03-11 2005-09-08 シエーリング アクチエンゲゼルシャフト Cdk−阻害性2−ヘテロアリール−ピリミジン類、それらの生成及び医薬としての使用
AR042486A1 (es) * 2002-12-18 2005-06-22 Glaxo Group Ltd Compuesto de quinolina y naftiridina halosustituido en la posicion 3, procedimiento para preparar el compuesto, composicion farmaceutica que lo comprende y su uso para preparar dicha composicion .
US7754714B2 (en) * 2004-05-18 2010-07-13 Rigel Pharmaceuticals, Inc. Cycloalkyl substituted pyrimidinediamine compounds and their uses
EP1794134A1 (de) * 2004-09-29 2007-06-13 Bayer Schering Pharma Aktiengesellschaft Substituierte 2-anilinopyrimidine als zellzyklus -kinase oder rezeptortyrosin-kinase inhibitoren, deren herstellung und verwendung als arzneimittel
US20070032514A1 (en) * 2005-07-01 2007-02-08 Zahn Stephan K 2,4-diamino-pyrimidines as aurora inhibitors
JP4332590B2 (ja) * 2005-12-21 2009-09-16 ファイザー・プロダクツ・インク 異常細胞増殖を治療するためのピリミジン誘導体
US8623887B2 (en) 2006-05-15 2014-01-07 Boehringer Ingelheim International Gmbh Compounds
TW200808325A (en) 2006-07-06 2008-02-16 Astrazeneca Ab Novel compounds
GB0619343D0 (en) 2006-09-30 2006-11-08 Vernalis R&D Ltd New chemical compounds
WO2008077885A2 (en) * 2006-12-22 2008-07-03 Boehringer Ingelheim International Gmbh 2- [(phenylamino) -pyrimidin-4ylamin0] -cyclopentane carboxamide derivatives and related compounds as inhibitors of kinases of the cell cycle for the treatment of cancer
BRPI0809715A2 (pt) 2007-04-16 2019-11-05 Hutchison Medipharma Entpr Ltd "composto, método de tratamento de um distúrbio relacionado com a angiogênese,método de inibição da atividade de receptor de domínio de inserto de quinase, método de inibição de angiogênese e método de tratamento de degeneração macular"
US8338439B2 (en) * 2008-06-27 2012-12-25 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
CA3031835C (en) * 2008-06-27 2021-09-07 Celgene Car Llc Heteroaryl compounds and uses thereof
AR074209A1 (es) 2008-11-24 2010-12-29 Boehringer Ingelheim Int Derivados de pirimidina utiles para el tratamiento del cancer
CN102482277B (zh) 2009-05-05 2017-09-19 达纳-法伯癌症研究所有限公司 表皮生长因子受体抑制剂及治疗障碍的方法

Also Published As

Publication number Publication date
EP2483249A1 (en) 2012-08-08
IN2012DN02714A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 2015-09-11
AU2010302648A1 (en) 2012-04-05
AR078513A1 (es) 2011-11-16
CN102695700A (zh) 2012-09-26
JP2013506636A (ja) 2013-02-28
AP2012006166A0 (en) 2012-04-30
NZ598614A (en) 2013-08-30
CL2012000825A1 (es) 2012-08-24
WO2011039344A1 (en) 2011-04-07
PE20121431A1 (es) 2012-11-10
TN2012000142A1 (en) 2013-09-19
EA201200552A1 (ru) 2013-03-29
US20110237598A1 (en) 2011-09-29
JP5702390B2 (ja) 2015-04-15
TW201124386A (en) 2011-07-16
ZA201201703B (en) 2014-05-28
MX2012003101A (es) 2012-04-11
ECSP12011830A (es) 2012-06-29
IL218543A0 (en) 2012-05-31
BR112012007300A2 (pt) 2017-11-07
PH12012500527A1 (en) 2012-10-22
UY32916A (es) 2011-04-29
EP2483249B1 (en) 2015-12-23
MA33606B1 (fr) 2012-09-01
CA2775418A1 (en) 2011-04-07
US8466155B2 (en) 2013-06-18

Similar Documents

Publication Publication Date Title
JP5702390B2 (ja) タンパク質チロシンキナーゼ2阻害剤としてのピリミジン誘導体
JP5622740B2 (ja) 新規化合物
KR102190087B1 (ko) 트라이아졸로피라진
EP2978757B1 (en) Indolinone analogues as brd4 inhibitors
EP3033335B1 (en) Pyridinones
US8785464B2 (en) Pyrimidine derivatives that inhibit FAK/PTK2
EP2435411B1 (en) 2,4-diaminopyrimidines for the treatment of diseases characterised by excessive or abnormal cell proliferation
JP2011505407A (ja) 過剰な又は異常な細胞増殖を特徴とする疾患を治療するためのジアミノピリジン
JP2013526559A (ja) 1H−イミダゾ[4,5−c]キノリン
EP2668178B1 (en) New 5-alkynyl-pyridines
HK1172027A (en) Pyrimidine derivatives as protein tyrosine kinase 2 inhibitors
HK1164857A (en) 2, 4-diaminopyrimidines for the treatment of diseases characterised by excessive or abnormal cell proliferation
TW201307321A (zh) 新苯甲基羥吲哚嘧啶

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20120501

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
PC1203 Withdrawal of no request for examination
WITN Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid