ES2237332B1 - Derivados de piridinio y quinolinio. - Google Patents

Derivados de piridinio y quinolinio.

Info

Publication number
ES2237332B1
ES2237332B1 ES200400072A ES200400072A ES2237332B1 ES 2237332 B1 ES2237332 B1 ES 2237332B1 ES 200400072 A ES200400072 A ES 200400072A ES 200400072 A ES200400072 A ES 200400072A ES 2237332 B1 ES2237332 B1 ES 2237332B1
Authority
ES
Spain
Prior art keywords
trifluoromethyl
alkoxy
optionally substituted
hydroxyl
halogen
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.)
Expired - Fee Related
Application number
ES200400072A
Other languages
English (en)
Spanish (es)
Other versions
ES2237332A1 (es
Inventor
Juan Carlos Lacal Sanjuan
Joaquin Campos Rosa
Miguel Angel Gallo Meza
Antonio Espinosa Ubeda
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.)
Consejo Superior de Investigaciones Cientificas CSIC
Universidad de Granada
Original Assignee
Consejo Superior de Investigaciones Cientificas CSIC
Universidad de Granada
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 to ES200400072A priority Critical patent/ES2237332B1/es
Application filed by Consejo Superior de Investigaciones Cientificas CSIC, Universidad de Granada filed Critical Consejo Superior de Investigaciones Cientificas CSIC
Priority to PT05708100T priority patent/PT1710236E/pt
Priority to JP2006548321A priority patent/JP5047627B2/ja
Priority to MXPA06007940A priority patent/MXPA06007940A/es
Priority to KR1020067016298A priority patent/KR101157206B1/ko
Priority to EP09157208A priority patent/EP2085386A3/en
Priority to EP05708100A priority patent/EP1710236B1/en
Priority to PCT/ES2005/070002 priority patent/WO2005068429A1/es
Priority to AT05708100T priority patent/ATE461918T1/de
Priority to US10/597,095 priority patent/US7781458B2/en
Priority to BRPI0506486-4A priority patent/BRPI0506486A/pt
Priority to DK05708100.2T priority patent/DK1710236T3/da
Priority to CA2553328A priority patent/CA2553328C/en
Priority to CN2005800024289A priority patent/CN1910153B/zh
Priority to DE602005020112T priority patent/DE602005020112D1/de
Priority to HK07108357.3A priority patent/HK1100441B/xx
Priority to ES05708100T priority patent/ES2343418T3/es
Priority to PL05708100T priority patent/PL1710236T3/pl
Publication of ES2237332A1 publication Critical patent/ES2237332A1/es
Application granted granted Critical
Publication of ES2237332B1 publication Critical patent/ES2237332B1/es
Priority to US12/856,196 priority patent/US8586613B2/en
Priority to JP2012062569A priority patent/JP5619805B2/ja
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • C07D401/10Heterocyclic 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 aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72Nitrogen atoms
    • C07D213/74Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10Antimycotics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • A61P33/02Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • 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
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38Nitrogen atoms
    • C07D215/42Nitrogen atoms attached in position 4
    • C07D215/44Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
ES200400072A 2004-01-14 2004-01-14 Derivados de piridinio y quinolinio. Expired - Fee Related ES2237332B1 (es)

Priority Applications (20)

Application Number Priority Date Filing Date Title
ES200400072A ES2237332B1 (es) 2004-01-14 2004-01-14 Derivados de piridinio y quinolinio.
DK05708100.2T DK1710236T3 (da) 2004-01-14 2005-01-11 Derivater af pyridin og quinolin
MXPA06007940A MXPA06007940A (es) 2004-01-14 2005-01-11 Derivados de piridinio y quinolinio.
KR1020067016298A KR101157206B1 (ko) 2004-01-14 2005-01-11 피리딘 및 퀴놀린 유도체
EP09157208A EP2085386A3 (en) 2004-01-14 2005-01-11 Pyridinium and quinolinium derivatives as Choline kinase inhibitors
EP05708100A EP1710236B1 (en) 2004-01-14 2005-01-11 Derivatives of pyridine and quinoline
JP2006548321A JP5047627B2 (ja) 2004-01-14 2005-01-11 ピリジニウムおよびキノリニウム誘導体
AT05708100T ATE461918T1 (de) 2004-01-14 2005-01-11 Derivate von pyridin und chinolin
US10/597,095 US7781458B2 (en) 2004-01-14 2005-01-11 Derivatives of pyridine and quinoline
BRPI0506486-4A BRPI0506486A (pt) 2004-01-14 2005-01-11 derivados de piridìnio e quinolìnio
PT05708100T PT1710236E (pt) 2004-01-14 2005-01-11 Derivados de piridínio e quinolínio
PCT/ES2005/070002 WO2005068429A1 (es) 2004-01-14 2005-01-11 Derivados de piridinio y quinolinio
PL05708100T PL1710236T3 (pl) 2004-01-14 2005-01-11 Pochodne pirydyny i chinoliny
DE602005020112T DE602005020112D1 (de) 2004-01-14 2005-01-11 Derivate von pyridin und chinolin
HK07108357.3A HK1100441B (en) 2004-01-14 2005-01-11 Derivatives of pyridine and quinoline
ES05708100T ES2343418T3 (es) 2004-01-14 2005-01-11 Derivados de piridinio y quinolinio.
CN2005800024289A CN1910153B (zh) 2004-01-14 2005-01-11 吡啶和喹啉衍生物
CA2553328A CA2553328C (en) 2004-01-14 2005-01-11 Pyridinium and quinolinium derivatives
US12/856,196 US8586613B2 (en) 2004-01-14 2010-08-13 Pyridinium and quinolinium derivatives
JP2012062569A JP5619805B2 (ja) 2004-01-14 2012-03-19 ピリジニウムおよびキノリニウム誘導体

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES200400072A ES2237332B1 (es) 2004-01-14 2004-01-14 Derivados de piridinio y quinolinio.

Publications (2)

Publication Number Publication Date
ES2237332A1 ES2237332A1 (es) 2005-07-16
ES2237332B1 true ES2237332B1 (es) 2006-11-01

Family

ID=34778265

Family Applications (2)

Application Number Title Priority Date Filing Date
ES200400072A Expired - Fee Related ES2237332B1 (es) 2004-01-14 2004-01-14 Derivados de piridinio y quinolinio.
ES05708100T Expired - Lifetime ES2343418T3 (es) 2004-01-14 2005-01-11 Derivados de piridinio y quinolinio.

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES05708100T Expired - Lifetime ES2343418T3 (es) 2004-01-14 2005-01-11 Derivados de piridinio y quinolinio.

Country Status (15)

Country Link
US (1) US7781458B2 (enExample)
EP (2) EP1710236B1 (enExample)
JP (2) JP5047627B2 (enExample)
KR (1) KR101157206B1 (enExample)
CN (1) CN1910153B (enExample)
AT (1) ATE461918T1 (enExample)
BR (1) BRPI0506486A (enExample)
CA (1) CA2553328C (enExample)
DE (1) DE602005020112D1 (enExample)
DK (1) DK1710236T3 (enExample)
ES (2) ES2237332B1 (enExample)
MX (1) MXPA06007940A (enExample)
PL (1) PL1710236T3 (enExample)
PT (1) PT1710236E (enExample)
WO (1) WO2005068429A1 (enExample)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8586613B2 (en) * 2004-01-14 2013-11-19 Universidad De Granada Pyridinium and quinolinium derivatives
CA2729857A1 (en) 2008-07-04 2010-01-07 Traslational Cancer Drugs Pharma, S.L. Methods for the treatment and diagnosis of cancer
US20100068302A1 (en) * 2008-09-17 2010-03-18 Traslational Cancer Drugs Pharma, S.L. Methods and compositions for the treatment of cancer
US20110212994A1 (en) * 2009-06-26 2011-09-01 Brian Clem Small Molecule Choline Kinase Inhibitors, Screening Assays, and Methods for Safe and Effective Treatment of Neoplastic Disorders
WO2012041493A1 (en) * 2010-09-28 2012-04-05 Julius-Maximilians-Universität Würzburg Aminoquinolinium salts, methods of their production and their use as active agents for biotechnological and medical applications against binary toxins
EP2468259A1 (en) * 2010-12-23 2012-06-27 Traslational Cancer Drugs Pharma, S.L. Pharmaceutical compositions of pyridinium and quinolinium derivatives
BR112013032857A2 (pt) 2011-06-20 2017-01-24 Traslational Cancer Drugs Pharma S L método para prever a resposta clínica à quimioterapia em um indivíduo com câncer
EP2758395A1 (en) * 2011-09-22 2014-07-30 Vertex Pharmaceuticals Inc. Compounds useful as inhibitors of choline kinase
ES2472367B1 (es) * 2012-12-28 2015-06-02 Universidad De Granada Inhibidores no simétricos de colina quinasa con actividad antitumoral y antimalárica
WO2015028662A1 (en) 2013-08-30 2015-03-05 Consejo Superior De Investigaciones Cientificas (Csic) Compositions and methods for characterization and amelioration of rheumatoid arthritis
ES2482290B1 (es) * 2014-06-05 2015-05-19 Universidad De Granada Inhibidores polares simétricos de colina cinasa con actividad antitumoral
JP6920411B2 (ja) 2016-07-25 2021-08-18 ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ コリンキナーゼ阻害剤としてのプリン及び3−デアザプリンアナログ
CN110997678B (zh) 2017-07-11 2023-02-21 内尔维亚诺医疗科学公司 作为胆碱激酶抑制剂的吡唑并喹唑啉衍生物
WO2025196502A1 (en) * 2024-03-20 2025-09-25 North Carolina Agricultural & Technical State University Choline kinase inhibitors as a therapeutic treatment for obesity

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4206215A (en) * 1976-02-25 1980-06-03 Sterling Drug Inc. Antimicrobial bis-[4-(substituted-amino)-1-pyridinium]alkanes
GB1533952A (en) * 1976-02-25 1978-11-29 Sterling Drug Inc Anti-microbial bis-pyridinium compounds
FR2498187A1 (fr) * 1981-01-16 1982-07-23 Rhone Poulenc Sante Procede de preparation d'amino-4 chloro-7 quinoleines
IL89026A (en) * 1988-01-29 1993-02-21 Lilly Co Eli Substituted quinolines and cinnolines, process for their preparation and fungicidal, insecticidal and miticidal compositions containing them
ES2117950B1 (es) 1996-08-02 1999-09-16 Univ Granada Nuevos compuestos que bloquean la biosintesis de fosforilcolina y su uso como segundo mensajero en proliferacion celular.

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CAMPOS, J. y col. Anticancer bisquaternary heterocyclic compounds: a racional design. Fármaco. 2003, Volumen 58, Nº 3, páginas 221-229, ISSN 0014-827X. Página 224, tabla 2, compuesto 3k con RN 468742-50-9. *
CAMPOS, J. y col. Quantitative structure-activity relationships for a series of symmetrical bisquaternary anticancer compounds. Bioorganic & Medicinal Chemistry. 2002, Volumen 10, Nº 7, páginas 2215-2231, ISSN 0968-0896. Página 2220, tabla 5, compuestos con RN 468742-49-6, 468742-50-9, 468742-51-0. Página 2224, 2º párrafo. 13 *
CONEJO-GARCÍA, A. y col. Choline kinase inhibitory effect and antiproliferative activity of new 1,1',1''-(benzene-1,3,5- triylmethylene)tris{4-[(disubstituted)amino]pyridinium} tribromides. European Journal of Medicinal Chemistry. 2003, Volumen 38, Nº 1, páginas 109-116, ISSN 0223-5234. Página 110, tabla I, compuesto 5 con RN 556795-28-9. Página 110, tabla I, compuestos 9,10,11 con RN 556795-32-5, 556795-33-6, 556795-34-7. Páginas 111-112. Chemistry. 13 *
GALANAKIS D. y col. Synthesis and Quantitative Structure- Activity. Relationship of Dequalinium Analogs as K+ Channel Blockers: Investigations on the Role of the Substituent at Position 4 of the Quinoline Ring. Journal of Medicinal Chemistry. 1995, Vol. 38, Nº 18, páginas 3536-46, ISSN 0022-2623. Compuesto con RN 167277-01-2, página 3537. *

Also Published As

Publication number Publication date
CN1910153B (zh) 2010-05-26
BRPI0506486A (pt) 2007-02-13
DK1710236T3 (da) 2010-07-12
JP2012149077A (ja) 2012-08-09
ATE461918T1 (de) 2010-04-15
PT1710236E (pt) 2010-06-18
ES2343418T3 (es) 2010-07-30
CA2553328C (en) 2012-05-15
JP5047627B2 (ja) 2012-10-10
MXPA06007940A (es) 2007-01-23
US20070185170A1 (en) 2007-08-09
EP1710236A1 (en) 2006-10-11
WO2005068429A1 (es) 2005-07-28
EP2085386A2 (en) 2009-08-05
KR101157206B1 (ko) 2012-07-06
PL1710236T3 (pl) 2010-08-31
HK1100441A1 (en) 2007-09-21
ES2237332A1 (es) 2005-07-16
EP1710236B1 (en) 2010-03-24
KR20060110364A (ko) 2006-10-24
US7781458B2 (en) 2010-08-24
DE602005020112D1 (de) 2010-05-06
CA2553328A1 (en) 2005-07-28
JP5619805B2 (ja) 2014-11-05
EP2085386A3 (en) 2009-10-28
CN1910153A (zh) 2007-02-07
JP2007517837A (ja) 2007-07-05

Similar Documents

Publication Publication Date Title
JP5619805B2 (ja) ピリジニウムおよびキノリニウム誘導体
Jafari et al. Design, synthesis and biological evaluation of novel benzo-and tetrahydrobenzo-[h] quinoline derivatives as potential DNA-intercalating antitumor agents
Al-Trawneh et al. Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents
Abuo-Rahma et al. Design, synthesis, antibacterial activity and physicochemical parameters of novel N-4-piperazinyl derivatives of norfloxacin
Dixit et al. Synthesis and in vitro antiplasmodial activities of fluoroquinolone analogs
Jin et al. Design, synthesis, and dual evaluation of quinoline and quinolinium iodide salt derivatives as potential anticancer and antibacterial agents
Fossa et al. Novel angular furo and thieno-quinolinones: Synthesis and preliminary photobiological studies
US2500131A (en) Di-nu-oxides of amino-substituted acridines and quinolines
Panda et al. New trifluoromethyl quinolone derivatives: Synthesis and investigation of antimicrobial properties
KR19990082201A (ko) 에이즈 치료제 또는 예방제
JP2007517837A5 (enExample)
Yuan et al. 3-(Benzo [d] thiazol-2-yl)-4-aminoquinoline derivatives as novel scaffold topoisomerase I inhibitor via DNA intercalation: design, synthesis, and antitumor activities
Digafie et al. Synthesis, Antibacterial, Antioxidant, and Molecular Modeling Studies of Novel [2, 3′‐Biquinoline]‐4‐Carboxylic Acid and Quinoline‐3‐Carbaldehyde Analogs
CN115043837B (zh) 一种4-咪唑并吡啶基硫异喹啉杂环化合物的合成方法及应用
Mathada et al. Synthesis and Antimicrobial Activity of Some 5-Substituted-3-phenyl-Nβ-(Substituted-2-oxo-2H-pyrano [2, 3-b] quinoline-3-carbonyl)-1H-indole-2-carboxyhydrazide
Siim et al. Hypoxia-selective antitumor agents. 15. Modification of rate of nitroreduction and extent of lysosomal uptake by polysubstitution of 4-(alkylamino)-5-nitroquinoline bioreductive drugs
US8586613B2 (en) Pyridinium and quinolinium derivatives
DK161384B (da) Pyrazolooe3,4,5-klaaacridinforbindelser og farmaceutiske praeparater indeholdende saadanne forbindelser
Lacal et al. Derivatives of pyridine and quinoline
HK1100441B (en) Derivatives of pyridine and quinoline
CN102731525A (zh) 苯并吗啉衍生物
CN109369676B (zh) 一种双-氟喹诺酮噁二唑脲类n-乙酰诺氟沙星衍生物及其制备方法和应用
CN109336902B (zh) 一种双-氟喹诺酮噁二唑脲类n-乙酰基环丙沙星衍生物及其制备方法和应用
CN109369675B (zh) 一种双-氟喹诺酮噁二唑脲类培氟沙星衍生物及其制备方法和应用
CN121108109A (zh) 一种靶向alk蛋白的protac化合物及其抗肿瘤应用

Legal Events

Date Code Title Description
EC2A Search report published

Date of ref document: 20050716

Kind code of ref document: A1

FG2A Definitive protection

Ref document number: 2237332B1

Country of ref document: ES

FD2A Announcement of lapse in spain

Effective date: 20181008