+

WO1993015056A1 - Derives de pyridone, leur prepartion et leur utilisation comme medicaments - Google Patents

Derives de pyridone, leur prepartion et leur utilisation comme medicaments Download PDF

Info

Publication number
WO1993015056A1
WO1993015056A1 PCT/EP1993/000175 EP9300175W WO9315056A1 WO 1993015056 A1 WO1993015056 A1 WO 1993015056A1 EP 9300175 W EP9300175 W EP 9300175W WO 9315056 A1 WO9315056 A1 WO 9315056A1
Authority
WO
WIPO (PCT)
Prior art keywords
pyridone
hydrochloride
benzylamidino
benzyl
amidino
Prior art date
Application number
PCT/EP1993/000175
Other languages
English (en)
Inventor
Robert John Ife
Colin Andrew Leach
Dashyant Dhanak
Original Assignee
Smithkline Beecham Intercredit B.V.
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 Smithkline Beecham Intercredit B.V. filed Critical Smithkline Beecham Intercredit B.V.
Priority to JP5512930A priority Critical patent/JPH07503022A/ja
Priority to EP93902251A priority patent/EP0625144A1/fr
Publication of WO1993015056A1 publication Critical patent/WO1993015056A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/60—Heterocyclic 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic 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
    • C07D215/16—Heterocyclic 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3

Definitions

  • compositions comprising a compound of structure (I) or a pharmaceutically acceptable salt thereof and a
  • Benzylamine hydrochloride (1.06 g, 0.006 mol) was suspended in dry tetrahydrofuran (20 ml), to which 2M trimethylaluminium in toluene (2.9 ml, 0.006 mol) was added dropwise at 5°C under nitrogen. The mixture was warmed to 50 °C, then treated with 1-(4-methylbenzyl)-3-cyano-2-pyridone (1.35 g, 0.006 mol) in dry tetrahydrofuran (20 ml) and left for 16 hours. After cooling, the mixture was poured onto a chloroform/silica slurry, washed with chloroform and then methanol.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention se rapporte à des dérivés de 2-pyridone de formule générale (I) dans laquelle Ar1 représente un cycle de phényle éventuellement substitué; Ar2 représente un cycle de phényle éventuellement substitué; R1 représente hydrogène ou alkyleC¿1-4; R?2 représente hydrogène ou alkyleC¿1-4; R?3 représente hydrogène ou alkyleC¿1-4?; R?4 et R5¿ sont identiques ou différents et représentent chacun hydrogène, alkyleC¿1-4? ou alkyleC1-4 Arl, ou R?4 et R5¿ forment conjointement un groupe (CH=CH)¿2?; et X représente CH2 ou NR?6¿ dans lequel R6 représente hydrogène au alkyleC¿1-4?. L'invention concerne également un sel desdits dérivés ainsi que l'utilisation de ceux-ci comme inhibiteurs de sécrétion d'acide gastrique.
PCT/EP1993/000175 1992-01-27 1993-01-26 Derives de pyridone, leur prepartion et leur utilisation comme medicaments WO1993015056A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP5512930A JPH07503022A (ja) 1992-01-27 1993-01-26 ピリドン誘導体，その製造方法およびその医薬としての使用
EP93902251A EP0625144A1 (fr) 1992-01-27 1993-01-26 Derives de pyridone, leur prepartion et leur utilisation comme medicaments

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9201694.8 1992-01-27
GB929201694A GB9201694D0 (en) 1992-01-27 1992-01-27 Compounds

Publications (1)

Publication Number Publication Date
WO1993015056A1 true WO1993015056A1 (fr) 1993-08-05

Family

ID=10709307

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/000175 WO1993015056A1 (fr) 1992-01-27 1993-01-26 Derives de pyridone, leur prepartion et leur utilisation comme medicaments

Country Status (5)

Country Link
EP (1) EP0625144A1 (fr)
JP (1) JPH07503022A (fr)
AU (1) AU3352693A (fr)
GB (1) GB9201694D0 (fr)
WO (1) WO1993015056A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7175854B2 (en) 2000-12-07 2007-02-13 Altana Pharma Ag Pharmaceutical preparation comprising an active dispersed on a matrix
US7951397B2 (en) 2002-02-20 2011-05-31 Nycomed Gmbh Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient
US8691849B2 (en) 2008-09-02 2014-04-08 Janssen Pharmaceuticals, Inc. 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors
US8691813B2 (en) 2008-11-28 2014-04-08 Janssen Pharmaceuticals, Inc. Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors
US8841323B2 (en) 2006-03-15 2014-09-23 Janssen Pharmaceuticals, Inc. 1, 4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of MGLUR2-receptors
US8906939B2 (en) 2007-03-07 2014-12-09 Janssen Pharmaceuticals, Inc. 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives
US8937060B2 (en) 2009-05-12 2015-01-20 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo [4,3-A] pyridine derivatives and their use for the treatment of prevention of neurological and psychiatric disorders
US8946205B2 (en) 2009-05-12 2015-02-03 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
US8993591B2 (en) 2010-11-08 2015-03-31 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo[4,3-a] pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors
US9012448B2 (en) 2010-11-08 2015-04-21 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors
US9067891B2 (en) 2007-03-07 2015-06-30 Janssen Pharmaceuticals, Inc. 1,4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of mGluR2-receptors
US9085577B2 (en) 2009-05-12 2015-07-21 Janssen Pharmaceuticals, Inc. 7-aryl-1,2,4-triazolo[4,3-A]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
US9114138B2 (en) 2007-09-14 2015-08-25 Janssen Pharmaceuticals, Inc. 1′,3′-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′] bipyridinyl-2′-ones
US9271967B2 (en) 2010-11-08 2016-03-01 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
US9708315B2 (en) 2013-09-06 2017-07-18 Janssen Pharmaceutica Nv 1,2,4-triazolo[4,3-a]pyridine compounds and their use as positive allosteric modulators of MGLUR2 receptors
US10106542B2 (en) 2013-06-04 2018-10-23 Janssen Pharmaceutica Nv Substituted 6,7-dihydropyrazolo[1,5-a]pyrazines as negative allosteric modulators of mGluR2 receptors
US10537573B2 (en) 2014-01-21 2020-01-21 Janssen Pharmaceutica Nv Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use
US11369606B2 (en) 2014-01-21 2022-06-28 Janssen Pharmaceutica Nv Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3299081A (en) * 1963-09-13 1967-01-17 Merck & Co Inc Chemical processes for preparing nu-substituted amidines
US4028084A (en) * 1974-10-11 1977-06-07 Rohm And Haas Company Derivatives of 3-carboxy pyrid-2-ones
US4284768A (en) * 1980-07-02 1981-08-18 American Home Products Corporation 1,2-Dihydro-4-amino-2-oxo-3-quinoline-carboxylic acid derivatives
EP0339768A1 (fr) * 1988-02-25 1989-11-02 Smithkline Beckman Intercredit B.V. Dérivés des 4-amino-3-acylquinoléines et leur utilisation pour l'inhibition de la sécrétion gastrique
EP0500297A1 (fr) * 1991-02-16 1992-08-26 FISONS plc Pyridinomes- et pyrimidinones substitués comme antagonistes d'angiotensine II

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3299081A (en) * 1963-09-13 1967-01-17 Merck & Co Inc Chemical processes for preparing nu-substituted amidines
US4028084A (en) * 1974-10-11 1977-06-07 Rohm And Haas Company Derivatives of 3-carboxy pyrid-2-ones
US4284768A (en) * 1980-07-02 1981-08-18 American Home Products Corporation 1,2-Dihydro-4-amino-2-oxo-3-quinoline-carboxylic acid derivatives
EP0339768A1 (fr) * 1988-02-25 1989-11-02 Smithkline Beckman Intercredit B.V. Dérivés des 4-amino-3-acylquinoléines et leur utilisation pour l'inhibition de la sécrétion gastrique
EP0500297A1 (fr) * 1991-02-16 1992-08-26 FISONS plc Pyridinomes- et pyrimidinones substitués comme antagonistes d'angiotensine II

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 95, no. 13, 28 September 1981, Columbus, Ohio, US; abstract no. 115245n, W.H. GUENDEL ET AL. 'Pseudobases from quinolinium salts and alkoxides.' page 675 ; *
TETRAHEDRON, (INCL. TETRAHEDRON REPORTS) vol. 36, no. 6, 1980, OXFORD GB pages 785 - 789 F.M. MORACCI ET AL. 'Covalent adducts from 1,3-disubstituted pyridinium salts and pyridine' *

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7951398B2 (en) 2000-12-07 2011-05-31 Nycomed Gmbh Pharmaceutical preparation comprising an active dispersed on a matrix
US7175854B2 (en) 2000-12-07 2007-02-13 Altana Pharma Ag Pharmaceutical preparation comprising an active dispersed on a matrix
US7951397B2 (en) 2002-02-20 2011-05-31 Nycomed Gmbh Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient
US8431154B2 (en) 2002-02-20 2013-04-30 Takeda Gmbh Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidone as excipient
US9468598B2 (en) 2002-02-20 2016-10-18 Astrazeneca Ab Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient
US9266834B2 (en) 2006-03-15 2016-02-23 Janssen Pharmaceuticals, Inc. 1, 4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of MGLUR2-receptors
US8841323B2 (en) 2006-03-15 2014-09-23 Janssen Pharmaceuticals, Inc. 1, 4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of MGLUR2-receptors
US9067891B2 (en) 2007-03-07 2015-06-30 Janssen Pharmaceuticals, Inc. 1,4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of mGluR2-receptors
US8906939B2 (en) 2007-03-07 2014-12-09 Janssen Pharmaceuticals, Inc. 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives
US9114138B2 (en) 2007-09-14 2015-08-25 Janssen Pharmaceuticals, Inc. 1′,3′-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′] bipyridinyl-2′-ones
US9132122B2 (en) 2007-09-14 2015-09-15 Janssen Pharmaceuticals, Inc. 1′,3′-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′]bipyridinyl-2′-ones
US11071729B2 (en) 2007-09-14 2021-07-27 Addex Pharmaceuticals S.A. 1′,3′-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′]bipyridinyl-2′-ones
US8691849B2 (en) 2008-09-02 2014-04-08 Janssen Pharmaceuticals, Inc. 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors
US8691813B2 (en) 2008-11-28 2014-04-08 Janssen Pharmaceuticals, Inc. Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors
US9085577B2 (en) 2009-05-12 2015-07-21 Janssen Pharmaceuticals, Inc. 7-aryl-1,2,4-triazolo[4,3-A]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
US8937060B2 (en) 2009-05-12 2015-01-20 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo [4,3-A] pyridine derivatives and their use for the treatment of prevention of neurological and psychiatric disorders
US9226930B2 (en) 2009-05-12 2016-01-05 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment of prevention of neurological and psychiatric disorders
US8946205B2 (en) 2009-05-12 2015-02-03 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
US9737533B2 (en) 2009-05-12 2017-08-22 Janssen Pharmaceuticals. Inc. 1,2,4-triazolo [4,3-A] pyridine derivatives and their use for the treatment of prevention of neurological and psychiatric disorders
US10071095B2 (en) 2009-05-12 2018-09-11 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo [4,3-A] pyridine derivatives and their use for the treatment of neurological and psychiatric disorders
US8993591B2 (en) 2010-11-08 2015-03-31 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo[4,3-a] pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors
US9271967B2 (en) 2010-11-08 2016-03-01 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
US9012448B2 (en) 2010-11-08 2015-04-21 Janssen Pharmaceuticals, Inc. 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors
US10584129B2 (en) 2013-06-04 2020-03-10 Janssen Pharmaceuticals Nv Substituted 6,7-dihydropyrazolo[1,5-a]pyrazines as negative allosteric modulators of mGluR2 receptors
US10106542B2 (en) 2013-06-04 2018-10-23 Janssen Pharmaceutica Nv Substituted 6,7-dihydropyrazolo[1,5-a]pyrazines as negative allosteric modulators of mGluR2 receptors
US9708315B2 (en) 2013-09-06 2017-07-18 Janssen Pharmaceutica Nv 1,2,4-triazolo[4,3-a]pyridine compounds and their use as positive allosteric modulators of MGLUR2 receptors
US10537573B2 (en) 2014-01-21 2020-01-21 Janssen Pharmaceutica Nv Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use
US11103506B2 (en) 2014-01-21 2021-08-31 Janssen Pharmaceutica Nv Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use
US11369606B2 (en) 2014-01-21 2022-06-28 Janssen Pharmaceutica Nv Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use
US12048696B2 (en) 2014-01-21 2024-07-30 Janssen Pharmaceutica Nv Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use

Also Published As

Publication number Publication date
JPH07503022A (ja) 1995-03-30
GB9201694D0 (en) 1992-03-11
EP0625144A1 (fr) 1994-11-23
AU3352693A (en) 1993-09-01

Similar Documents

Publication Publication Date Title
EP0322133B1 (fr) Dérivés de quinazolinone
WO1993015056A1 (fr) Derives de pyridone, leur prepartion et leur utilisation comme medicaments
US4935431A (en) Substituted 7-amino-thienopyridine derivatives as gastric acid secretion inhibitors
US5280026A (en) Thienopyrimidines
AU598299B2 (en) 4-aminoquinoline derivatives
EP0393926B1 (fr) Dérivés de la 1-amino-isoquinoléine
IE50682B1 (en) Imidazo(1,2-a)pyridines,process for their preparation and pharmaceutical compositions containing them
US5051508A (en) Dihydropyrrolo quinoline derivatives
US5409943A (en) [(alkoxy)pyridinyl]amine compounds which are useful in the treatment of gastrointestinal disorders
EP0404355A1 (fr) Dérivés de pyridopyrimidine, leur procédé de préparation et compositions pharmaceutiques les contenant
AU606508B2 (en) 4-amino-3-acylquinoline derivatives and their use as inhibitors of gastric secretion
EP0404322B1 (fr) Dérivés de quinazoline
US5089498A (en) Substituted 4-aminoquinoline derivatives as gastric acid secretion inhibitors
US5006535A (en) Substituted heterocylic 4-aminoquinoline derivatives as gastric acid secretion inhibitors
US5420135A (en) Substituted quinoline derivatives
KR910005854B1 (ko) 헤테로사이클릭 그룹을 함유하는 이미다조 퀴놀린 유도체의 제조방법
US4988695A (en) Pyrrolocinnolines for use as inhibitors of gastric acid secretion
WO1993015071A1 (fr) Derives de thiazolyle-pyridine et leur utilisation comme inhibiteurs de secretion d'acide gastrique
EP0404356A1 (fr) Dérivés de thiénopyrimidine substitués, leur préparation, compositions pharmaceutiques et application médicale
US5082848A (en) Substituted 4-aminoquinoline derivatives as gastric acid secretion inhibitors
US5049567A (en) Substituted 4-aminoquinazoline derivatives and method of use
US4703044A (en) Imidazoquinolines containing other heterocyclic groups, useful as anti-ulcer or anti-secretory agents
US4666900A (en) Anti-ulcer and anti-hypersecretion dibenzoimidazothiazepine derivatives, compositions, and method of use therefor

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU CA JP KR NZ US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 1993902251

Country of ref document: EP

ENP Entry into the national phase

Ref country code: US

Ref document number: 1994 256671

Date of ref document: 19940720

Kind code of ref document: A

Format of ref document f/p: F

WWP Wipo information: published in national office

Ref document number: 1993902251

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: CA

WWW Wipo information: withdrawn in national office

Ref document number: 1993902251

Country of ref document: EP

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载