CO6781549A2 - Uso de ligandos sigma en dolor por cáncer de huesos - Google Patents

Uso de ligandos sigma en dolor por cáncer de huesos

Info

Publication number
CO6781549A2
CO6781549A2 CO13155721A CO13155721A CO6781549A2 CO 6781549 A2 CO6781549 A2 CO 6781549A2 CO 13155721 A CO13155721 A CO 13155721A CO 13155721 A CO13155721 A CO 13155721A CO 6781549 A2 CO6781549 A2 CO 6781549A2
Authority
CO
Colombia
Prior art keywords
bone cancer
cancer pain
sigma ligands
sigma
ligands
Prior art date
Application number
CO13155721A
Other languages
English (en)
Spanish (es)
Inventor
Daniel Zamanillo-Castanedo
Hernandez Jose Miguel Vela
Carlos Plata-Salaman
Original Assignee
Esteve Labor Dr
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 Esteve Labor Dr filed Critical Esteve Labor Dr
Publication of CO6781549A2 publication Critical patent/CO6781549A2/es

Links

Classifications

    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further 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
    • A61K31/435—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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Emergency Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Compression, Expansion, Code Conversion, And Decoders (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Steroid Compounds (AREA)
CO13155721A 2010-12-03 2013-07-02 Uso de ligandos sigma en dolor por cáncer de huesos CO6781549A2 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP10382330A EP2460519A1 (en) 2010-12-03 2010-12-03 Use of sigma ligands in bone cancer pain

Publications (1)

Publication Number Publication Date
CO6781549A2 true CO6781549A2 (es) 2013-10-31

Family

ID=43629676

Family Applications (1)

Application Number Title Priority Date Filing Date
CO13155721A CO6781549A2 (es) 2010-12-03 2013-07-02 Uso de ligandos sigma en dolor por cáncer de huesos

Country Status (35)

Country Link
US (1) US20130324535A1 (enExample)
EP (2) EP2460519A1 (enExample)
JP (1) JP6027014B2 (enExample)
KR (1) KR101855358B1 (enExample)
CN (1) CN103313709B (enExample)
AR (1) AR084730A1 (enExample)
BR (1) BR112013013369A8 (enExample)
CA (1) CA2819442C (enExample)
CO (1) CO6781549A2 (enExample)
CY (1) CY1119030T1 (enExample)
DK (1) DK2646025T3 (enExample)
ES (1) ES2626672T3 (enExample)
HR (1) HRP20170818T1 (enExample)
HU (1) HUE033488T2 (enExample)
IL (1) IL226706A (enExample)
LT (1) LT2646025T (enExample)
MA (1) MA34878B1 (enExample)
ME (1) ME02852B (enExample)
MX (1) MX343773B (enExample)
MY (1) MY171994A (enExample)
NZ (1) NZ612119A (enExample)
PH (1) PH12013501127A1 (enExample)
PL (1) PL2646025T3 (enExample)
PT (1) PT2646025T (enExample)
RS (1) RS56081B1 (enExample)
RU (1) RU2585095C2 (enExample)
SG (1) SG190745A1 (enExample)
SI (1) SI2646025T1 (enExample)
SM (1) SMT201700270T1 (enExample)
TN (1) TN2013000227A1 (enExample)
TR (1) TR201708567T4 (enExample)
TW (1) TWI629060B (enExample)
UA (1) UA112638C2 (enExample)
WO (1) WO2012072782A1 (enExample)
ZA (1) ZA201304966B (enExample)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2116539A1 (en) 2008-04-25 2009-11-11 Laboratorios Del. Dr. Esteve, S.A. 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof
EP2353598A1 (en) 2010-02-04 2011-08-10 Laboratorios Del. Dr. Esteve, S.A. Sigma ligands for use in the prevention and/or treatment of postoperative pain
EP2353591A1 (en) 2010-02-04 2011-08-10 Laboratorios Del. Dr. Esteve, S.A. Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof
EP2388005A1 (en) 2010-05-21 2011-11-23 Laboratorios Del. Dr. Esteve, S.A. Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy
EP2415471A1 (en) 2010-08-03 2012-02-08 Laboratorios Del. Dr. Esteve, S.A. Use of sigma ligands in opioid-induced hyperalgesia
EP2426111A1 (en) * 2010-08-09 2012-03-07 Laboratorios Del. Dr. Esteve, S.A. 4-[-2-[[5-methyl-1-(2-naphtalenyl)-1h-pyrazol-3-yl]oxy]ethyl]morpholine hydrochloride amorphous solid forms
EP2524694A1 (en) 2011-05-19 2012-11-21 Laboratorios Del. Dr. Esteve, S.A. Use of sigma ligands in diabetes type-2 associated pain
EP2792352A1 (en) 2013-04-16 2014-10-22 Laboratorios Del. Dr. Esteve, S.A. Alpha-2 adrenoreceptor and sigma receptor ligand combinations
EP2818166A1 (en) * 2013-06-26 2014-12-31 Laboratorios del Dr. Esteve S.A. Use of sigma receptor ligands for the prevention and treatment of pain associated to interstitial cystitis/bladder pain syndrome (IC/BPS)
MX2016002892A (es) * 2013-09-12 2016-06-10 Esteve Labor Dr Combinaciones de ligando de receptores sigma y aine.
SG11201604480PA (en) 2013-12-17 2016-07-28 Esteve Labor Dr SEROTONIN-NOREPINEPHRINE REUPTAKE INHIBITORS (SNRIs) AND SIGMA RECEPTOR LIGANDS COMBINATIONS
MX2016007286A (es) 2013-12-17 2016-08-04 Esteve Labor Dr Combinaciones de gabapentinoides y ligandos de receptores sigma.
EP2929883A1 (en) * 2014-04-08 2015-10-14 Institut Pasteur Pyrazole derivatives as dihydroorotate dehydrogenase (DHODH) inhibitors
WO2018011169A1 (en) * 2016-07-12 2018-01-18 Laboratorios Del Dr. Esteve, S.A. Use of sigma receptor ligands in post-herpetic pain
EP3415143A1 (en) * 2017-06-16 2018-12-19 Kai-Uwe Kern Bromhexine for the treatment of pain
WO2019224184A1 (en) * 2018-05-21 2019-11-28 Ipsen Biopharm Limited Suppression of bone cancer-induced allodynia
AU2019387370A1 (en) 2018-11-30 2021-06-10 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
CN112341397B (zh) * 2019-08-09 2023-05-23 成都苑东生物制药股份有限公司 吡嗪类衍生物或盐、异构体、其制备方法及用途
KR102744822B1 (ko) 2020-06-05 2024-12-20 주식회사 허밍아비스 발열체 조성물 및 이를 이용한 마스크 제조방법

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1832928B (zh) * 2003-06-26 2012-07-04 诺瓦提斯公司 以5元杂环为基础的p38激酶抑制剂
MX2007002341A (es) * 2004-08-27 2007-09-25 Esteve Labor Dr Inhibidores del receptor sigma.
KR101352012B1 (ko) * 2004-08-27 2014-01-15 라보라토리오스 델 드라. 에스테브.에스.에이. 시그마 수용체 저해제
WO2007098953A1 (en) * 2006-03-01 2007-09-07 Laboratorios Del Dr. Esteve, S.A. Pyrazole derivatives as sigma receptor inhibitors
EP2116539A1 (en) * 2008-04-25 2009-11-11 Laboratorios Del. Dr. Esteve, S.A. 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof
EP2113501A1 (en) * 2008-04-25 2009-11-04 Laboratorios Del. Dr. Esteve, S.A. 5-Methyl-1-(naphthalen-2-YL)-1H-Pyrazoles useful as sigma receptor inhibitors
EP2353591A1 (en) * 2010-02-04 2011-08-10 Laboratorios Del. Dr. Esteve, S.A. Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof

Also Published As

Publication number Publication date
SI2646025T1 (sl) 2017-07-31
JP2014501732A (ja) 2014-01-23
TW201249805A (en) 2012-12-16
NZ612119A (en) 2014-06-27
ZA201304966B (en) 2014-09-25
CA2819442C (en) 2018-06-12
LT2646025T (lt) 2017-06-12
PL2646025T3 (pl) 2017-09-29
CN103313709A (zh) 2013-09-18
AU2011334880B2 (en) 2016-09-15
AR084730A1 (es) 2013-06-05
DK2646025T3 (en) 2017-06-06
AU2011334880A1 (en) 2013-07-11
KR20130135881A (ko) 2013-12-11
TWI629060B (zh) 2018-07-11
SMT201700270T1 (it) 2017-07-18
ES2626672T3 (es) 2017-07-25
TN2013000227A1 (en) 2014-11-10
EP2646025B1 (en) 2017-03-15
ME02852B (me) 2018-04-20
CA2819442A1 (en) 2012-06-07
BR112013013369A2 (pt) 2016-09-06
WO2012072782A1 (en) 2012-06-07
HUE033488T2 (en) 2017-12-28
MX343773B (es) 2016-11-23
PT2646025T (pt) 2017-06-26
CN103313709B (zh) 2017-05-24
CY1119030T1 (el) 2018-01-10
RS56081B1 (sr) 2017-10-31
TR201708567T4 (tr) 2019-01-21
US20130324535A1 (en) 2013-12-05
PH12013501127A1 (en) 2020-10-19
MA34878B1 (fr) 2014-02-01
EP2646025A1 (en) 2013-10-09
HRP20170818T1 (hr) 2017-08-25
MY171994A (en) 2019-11-11
RU2013130222A (ru) 2015-01-10
BR112013013369A8 (pt) 2018-01-09
SG190745A1 (en) 2013-07-31
MX2013006140A (es) 2013-07-03
IL226706A (en) 2015-07-30
KR101855358B1 (ko) 2018-05-04
UA112638C2 (uk) 2016-10-10
JP6027014B2 (ja) 2016-11-16
RU2585095C2 (ru) 2016-05-27
EP2460519A1 (en) 2012-06-06

Similar Documents

Publication Publication Date Title
TN2013000227A1 (en) Use of sigma ligands in bone cancer pain
EA201300242A1 (ru) Фармацевтические композиции, содержащие замещенные ациланилиды
CO6680628A2 (es) Uso de ligandos sigma en la hiperalgesia inducida por opioides
EA201171367A1 (ru) Винилиндазолильные соединения
MX2010000465A (es) Metodos y composiciones para el tratamiento de cancer, tumores y alteraciones relacionadas con tumores.
MX2014011134A (es) Compuestos de carbamato y preparacion y uso de los mismos.
BR112015011756A2 (pt) inibidores da glutamase e métodos de uso
MX2012007098A (es) Derivados fenolicos y su uso farmaceutico o cosmetico.
EA200970737A1 (ru) Оксабициклогептаны и оксабициклогептены, их получение и применение
CL2015001250A1 (es) Compuestos derivados de triazolopirazinas, inhibidores de brd4; preparacion farmaceutica; y su uso en el tratamiento y/o la prevencion de cancer, tal como cancer de pulmon, higado, colon, cerebro, tiroides, mamas, entre otros.
MX343687B (es) Compuestos sulfonamida tricíclica y métodos para su fabricación y uso.
BR112013001613A2 (pt) compostos tricíclicos e métodos para fazer e usar os mesmos.
CL2009000545A1 (es) Uso de un antagonista de c-met y un antagonista de her para el tratamiento de cancer.
MX339201B (es) Compuestos de sulfonamida y métodos para elaborarlos y usarlos.
NI201200175A (es) Métodos de tratamiento de cáncer de vejiga
PH12019501393A1 (en) Afucosylated anti-fgfr2iiib antibodies
CR20120202A (es) Métodos y composiciones para tratar cáncer
EA201400178A1 (ru) Лечение рака молочной железы
CL2008002381A1 (es) Oligonucleotido inmunoestimulador; composicion farmaceutica que lo comprende; y su uso para tratar un trastorno o afeccion en un sujeto, incluyendo cancer.
MX2014008706A (es) Compuestos tricíclicos de sulfonamida y métodos para elaborarlos y usarlos.
MX2014008705A (es) Compuestos tricíclicos de sulfona y métodos para elaborarlos y utilizarlos.
UA113849C2 (xx) Застосування сигма-лігандів при болю, пов'язаному з діабетом 2 типу
TN2016000229A1 (en) Gabapentinoids and sigma receptor ligands combinations.
CL2013003324A1 (es) Composicion que comprende quimioterapia con paclitaxel y carboplatino y un oligonucleotido anti-clusterina; uso de la composición para el tratamiento de un paciente humano que padece cancer de pulmón.
MX359181B (es) Hidrolizado de colágeno y uso del mismo.

Legal Events

Date Code Title Description
FA Application withdrawn