CN101679239B - 组蛋白脱乙酰酶抑制剂 - Google Patents

组蛋白脱乙酰酶抑制剂 Download PDF

Info

Publication number
CN101679239B
CN101679239B CN200880015207.9A CN200880015207A CN101679239B CN 101679239 B CN101679239 B CN 101679239B CN 200880015207 A CN200880015207 A CN 200880015207A CN 101679239 B CN101679239 B CN 101679239B
Authority
CN
China
Prior art keywords
compound
alkyl
pyrrolidin
phenyl
group
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
CN200880015207.9A
Other languages
English (en)
Chinese (zh)
Other versions
CN101679239A (zh
Inventor
西尔维·弗雷切特
卢伯·伊萨科维克
伊莎贝尔·帕奎因
西蒙·罗伊
奥斯卡·莫拉戴
阿卡迪·韦斯伯格
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.)
7503547 Canada Co
Original Assignee
Methylgene Inc
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 Methylgene Inc filed Critical Methylgene Inc
Publication of CN101679239A publication Critical patent/CN101679239A/zh
Application granted granted Critical
Publication of CN101679239B publication Critical patent/CN101679239B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/12—Heterocyclic 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
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/04—Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/04—Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
CN200880015207.9A 2007-03-13 2008-03-12 组蛋白脱乙酰酶抑制剂 Expired - Fee Related CN101679239B (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US90673307P 2007-03-13 2007-03-13
US60/906,733 2007-03-13
US12/043,450 US8030344B2 (en) 2007-03-13 2008-03-06 Inhibitors of histone deacetylase
US12/043,450 2008-03-06
PCT/CA2008/000455 WO2008109994A1 (en) 2007-03-13 2008-03-12 Inhibitors of histone deacetylase

Publications (2)

Publication Number Publication Date
CN101679239A CN101679239A (zh) 2010-03-24
CN101679239B true CN101679239B (zh) 2014-12-10

Family

ID=39758948

Family Applications (1)

Application Number Title Priority Date Filing Date
CN200880015207.9A Expired - Fee Related CN101679239B (zh) 2007-03-13 2008-03-12 组蛋白脱乙酰酶抑制剂

Country Status (9)

Country Link
US (2) US8030344B2 (enExample)
EP (1) EP2134680B1 (enExample)
JP (2) JP2010520893A (enExample)
KR (2) KR20150080025A (enExample)
CN (1) CN101679239B (enExample)
CA (1) CA2680467C (enExample)
ES (1) ES2565243T3 (enExample)
TW (1) TWI549676B (enExample)
WO (1) WO2008109994A1 (enExample)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8030344B2 (en) * 2007-03-13 2011-10-04 Methylgene Inc. Inhibitors of histone deacetylase
BRPI0817897A2 (pt) * 2007-11-02 2019-09-24 Methylgene Inc composto, composição, e, métodos de inibição da atividade hdac, e de tratamento de uma doença responsiva a um inibidor de atividade hdac
AU2009289649B2 (en) 2008-09-03 2016-05-05 Biomarin Pharmaceutical Inc. Compositions including 6-aminohexanoic acid derivatives as HDAC inhibitors
KR20110117194A (ko) * 2009-02-23 2011-10-26 에프. 호프만-라 로슈 아게 암 치료를 위한 신규한 오르토-아미노아미드
IN2012DN03807A (enExample) 2009-10-30 2015-08-28 Massachusetts Inst Technology
WO2012068589A2 (en) * 2010-11-19 2012-05-24 Constellation Pharmaceuticals Modulators of methyl modifying enzymes, compositions and uses thereof
US8957066B2 (en) 2011-02-28 2015-02-17 Biomarin Pharmaceutical Inc. Histone deacetylase inhibitors
US10059723B2 (en) 2011-02-28 2018-08-28 Biomarin Pharmaceutical Inc. Histone deacetylase inhibitors
JP6250403B2 (ja) 2011-02-28 2017-12-20 バイオマリン ファーマシューティカル インク ヒストン脱アセチル化酵素阻害剤
CN102775368B (zh) * 2011-05-10 2016-08-17 上海驺虞医药科技有限公司 一类噻唑类化合物及其制备方法和用途
US9206128B2 (en) 2011-11-18 2015-12-08 Constellation Pharmaceuticals, Inc. Modulators of methyl modifying enzymes, compositions and uses thereof
WO2013075084A1 (en) 2011-11-18 2013-05-23 Constellation Pharmaceuticals Modulators of methyl modifying enzymes, compositions and uses thereof
CA2862289C (en) 2012-02-10 2019-11-26 Constellation Pharmaceuticals, Inc. Modulators of methyl modifying enzymes, compositions and uses thereof
PT2970139T (pt) 2013-03-15 2018-08-01 Biomarin Pharm Inc Inibidores de hdac
WO2014151142A1 (en) 2013-03-15 2014-09-25 Constellation Pharmaceuticals, Inc. Modulators of methyl modifying enzymes, compositions and uses thereof
WO2015023915A1 (en) 2013-08-15 2015-02-19 Constellation Pharmaceuticals, Inc. Indole derivatives as modulators of methyl modifying enzymes, compositions and uses thereof
US9274117B2 (en) * 2013-12-21 2016-03-01 Catholic University Industry Academic Use of SIRT7 as novel cancer therapy target and method for treating cancer using the same
US9636298B2 (en) 2014-01-17 2017-05-02 Methylgene Inc. Prodrugs of compounds that enhance antifungal activity and compositions of said prodrugs
GB201501870D0 (en) 2015-02-04 2015-03-18 Cancer Rec Tech Ltd Autotaxin inhibitors
CA2990660A1 (en) * 2015-07-02 2017-01-05 Biomarin Pharmaceutical Inc. Histone deacetylase inhibitors
US10577350B2 (en) 2015-08-28 2020-03-03 Constellation Pharmaceuticals, Inc. Crystalline forms of (R)-N-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)ethyl)-1H-indole-3-carboxamide
EP3529242A1 (en) 2016-10-19 2019-08-28 Constellation Pharmaceuticals, Inc. Synthesis of inhibitors of ezh2

Family Cites Families (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2754286A (en) * 1951-10-15 1956-07-10 Du Pont Aldehydes and their acetals
CH431764A (de) * 1959-05-06 1967-03-15 Sandoz Ag Verfahren zur Herstellung metallhaltiger Reaktivfarbstoffe
US3263924A (en) * 1963-09-13 1966-08-02 Dole Valve Co Heating and cooling zone valve
US4994479A (en) * 1985-04-03 1991-02-19 Yamanouchi Pharmaceutical Co., Ltd. Phenylene derivatives and anti-allergic use thereof
US5149797A (en) * 1990-02-15 1992-09-22 The Worcester Foundation For Experimental Biology Method of site-specific alteration of rna and production of encoded polypeptides
US5332750A (en) * 1991-09-04 1994-07-26 Merck Patent Gesellschaft Mit Beschrankter Haftung 1,2-dihydro-2-oxopyridines
US5652355A (en) * 1992-07-23 1997-07-29 Worcester Foundation For Experimental Biology Hybrid oligonucleotide phosphorothioates
DE19510957A1 (de) 1995-03-25 1996-09-26 Huels Chemische Werke Ag Eingedickter Bodenverfestiger, sowie diesen enthaltende verpackte Fertigmischung für Bodenbehandlungen
US6174905B1 (en) 1996-09-30 2001-01-16 Mitsui Chemicals, Inc. Cell differentiation inducer
US6794392B1 (en) * 1996-09-30 2004-09-21 Schering Aktiengesellschaft Cell differentiation inducer
JP4105451B2 (ja) 1996-09-30 2008-06-25 バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト 分化誘導剤
US6034251A (en) * 1997-11-07 2000-03-07 Schering Corporation Phenyl-alkyl-imidazoles
US5905084A (en) * 1997-11-14 1999-05-18 Eli Lilly And Company 5-HTIF -agonists effective in treating migraine
JPH11318492A (ja) * 1998-03-09 1999-11-24 Aisin Seiki Co Ltd 蛍光発生性基質を含有する組成物
JPH11269146A (ja) 1998-03-24 1999-10-05 Mitsui Chem Inc 分化誘導剤
JP4405602B2 (ja) 1998-04-16 2010-01-27 バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト ヒストン脱アセチル化酵素阻害剤
JP2000256194A (ja) 1999-01-06 2000-09-19 Mitsui Chemicals Inc 核内レセプタ作動薬およびその効果増強剤
US6653309B1 (en) * 1999-04-26 2003-11-25 Vertex Pharmaceuticals Incorporated Inhibitors of IMPDH enzyme technical field of the invention
WO2000071703A2 (en) 1999-05-03 2000-11-30 Methylgene Inc. Inhibition of histone deacetylase
JP4360660B2 (ja) 1999-11-09 2009-11-11 三井化学株式会社 モノアシルフェニレンジアミン誘導体の精製法
CA2391952C (en) 1999-11-23 2012-01-31 Methylgene Inc. Inhibitors of histone deacetylase
AU2001241128A1 (en) * 2000-03-14 2001-09-24 Fujisawa Pharmaceutical Co. Ltd. Novel amide compounds
AU2001248701A1 (en) 2000-03-24 2001-10-03 Methylgene, Inc. Inhibitors of histone deacetylase
WO2002069947A2 (en) 2001-01-12 2002-09-12 Methylgene, Inc. Antisense oligonucleotides and trichostatin analogue histone deacetylase-4 inhibitors against cancer
US7868204B2 (en) * 2001-09-14 2011-01-11 Methylgene Inc. Inhibitors of histone deacetylase
US6897220B2 (en) 2001-09-14 2005-05-24 Methylgene, Inc. Inhibitors of histone deacetylase
WO2003024448A2 (en) 2001-09-14 2003-03-27 Methylgene, Inc. Inhibitors of histone deacetylase
WO2003066889A2 (en) * 2002-02-07 2003-08-14 Axys Pharmaceuticals, Inc. Assay for acytyltransferase or deacetylase activity
AU2003218737B2 (en) 2002-03-13 2008-04-10 Janssen Pharmaceutica N.V. Inhibitors of histone deacetylase
CA2476067C (en) 2002-03-13 2011-09-20 Janssen Pharmaceutica N.V. Carbonylamino-derivatives as novel inhibitors of histone deacetylase
ES2306880T3 (es) 2002-03-13 2008-11-16 Janssen Pharmaceutica Nv Derivados de sulfonilamino como inhibidores novedosos de la histona desacetilasa.
EA007270B1 (ru) 2002-03-13 2006-08-25 Янссен Фармацевтика Н.В. Пиперазинил-, пиперидинил- и морфолинилпроизводные как новые ингибиторы гистондеацетилазы
ATE395343T1 (de) 2002-03-13 2008-05-15 Janssen Pharmaceutica Nv Sulfonylderivate als histone-deacetylase- inhibitoren
US7169737B2 (en) * 2002-03-14 2007-01-30 Nippon Soda Co., Ltd. Phenolic compound and recording material using the same
TWI319387B (en) * 2002-04-05 2010-01-11 Astrazeneca Ab Benzamide derivatives
GB0209715D0 (en) * 2002-04-27 2002-06-05 Astrazeneca Ab Chemical compounds
US20040072770A1 (en) 2002-07-03 2004-04-15 Besterman Jeffrey M. Methods for specifically inhibiting histone deacetylase-7 and 8
EP1551795A1 (en) 2002-10-17 2005-07-13 Methylgene, Inc. Inhibitors of histone deacetylase
US7135575B2 (en) * 2003-03-03 2006-11-14 Array Biopharma, Inc. P38 inhibitors and methods of use thereof
TW200505902A (en) * 2003-03-20 2005-02-16 Schering Corp Cannabinoid receptor ligands
CA2539117A1 (en) 2003-09-24 2005-04-07 Methylgene Inc. Inhibitors of histone deacetylase
US7253204B2 (en) * 2004-03-26 2007-08-07 Methylgene Inc. Inhibitors of histone deacetylase
EP1735319B1 (en) 2004-03-26 2017-05-03 MethylGene Inc. Inhibitors of histone deacetylase
AU2005336881A1 (en) * 2004-09-22 2007-05-24 Methylgene Inc. Histone deacetylase whole cell enzyme assay
JP2008524246A (ja) * 2004-12-16 2008-07-10 タケダ サン ディエゴ インコーポレイテッド ヒストンデアセチラーゼ阻害剤
JP4853824B2 (ja) * 2005-01-20 2012-01-11 アステラス製薬株式会社 キノロン誘導体を有効成分とする医薬組成物
EP1874295A4 (en) * 2005-04-20 2009-08-12 Merck & Co Inc benzothiophene
WO2006122319A2 (en) 2005-05-11 2006-11-16 Takeda San Diego, Inc. Histone deacetylase inhibitors
AU2006248938B2 (en) * 2005-05-18 2011-09-29 Janssen Pharmaceutica N.V. Substituted aminopropenyl piperidine or morpholine derivatives as novel inhibitors of histone deacetylase
ZA200800901B (en) * 2005-07-14 2010-05-26 Takeda San Diego Inc Histone deacetylase inhibitors
WO2007055942A2 (en) * 2005-11-03 2007-05-18 Merck & Co., Inc. Substituted nicotinamide compounds
AR057579A1 (es) * 2005-11-23 2007-12-05 Merck & Co Inc Compuestos espirociclicos como inhibidores de histona de acetilasa (hdac)
WO2007084390A2 (en) * 2006-01-13 2007-07-26 Takeda San Diego, Inc. Histone deacetylase inhibitors
ES2452820T3 (es) * 2006-04-07 2014-04-02 Methylgene, Inc. Derivados de benzamida como inhibidores de histona desacetilasa
US8030344B2 (en) * 2007-03-13 2011-10-04 Methylgene Inc. Inhibitors of histone deacetylase

Also Published As

Publication number Publication date
EP2134680A1 (en) 2009-12-23
JP2014159417A (ja) 2014-09-04
CA2680467C (en) 2016-11-08
HK1142597A1 (en) 2010-12-10
EP2134680A4 (en) 2012-03-07
ES2565243T3 (es) 2016-04-01
TWI549676B (zh) 2016-09-21
US20110212965A1 (en) 2011-09-01
CN101679239A (zh) 2010-03-24
KR20090119004A (ko) 2009-11-18
JP2010520893A (ja) 2010-06-17
JP5885311B2 (ja) 2016-03-15
WO2008109994A1 (en) 2008-09-18
US8354445B2 (en) 2013-01-15
KR101678611B1 (ko) 2016-11-22
US20080227826A1 (en) 2008-09-18
KR20150080025A (ko) 2015-07-08
CA2680467A1 (en) 2008-09-18
TW200848015A (en) 2008-12-16
EP2134680B1 (en) 2016-01-13
US8030344B2 (en) 2011-10-04

Similar Documents

Publication Publication Date Title
CN101679239A (zh) 组蛋白脱乙酰酶抑制剂
EP1735319B1 (en) Inhibitors of histone deacetylase
US8673911B2 (en) Inhibitors of histone deacetylase
ES2452820T3 (es) Derivados de benzamida como inhibidores de histona desacetilasa
JP5746860B2 (ja) ヒストンデアセチラーゼ阻害剤
KR101512284B1 (ko) 치환된 피라졸로-퀴나졸린 유도체, 이의 제조방법, 및 키나제 억제제로서의 이의 용도
US20070293530A1 (en) Sulfamide and sulfamate derivatives as histone deacetylase inhibitors
SK2082002A3 (en) 3(5)-ureido-pyrazole derivatives, process for their preparation and their use as antitumor agents
TW201514157A (zh) 環丙胺化合物及其用途
KR20180022840A (ko) 히스톤 데아세틸라제 저해제
HK1142597B (en) Inhibitors of histone deacetylase
HK1095044A (en) Inhibitors of histone deacetylase
HK1126769B (en) Benzamide derivatives as inhibitors of histone deacetylase

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
REG Reference to a national code

Ref country code: HK

Ref legal event code: DE

Ref document number: 1142597

Country of ref document: HK

ASS Succession or assignment of patent right

Owner name: CANADA CO., LTD., 7503547

Free format text: FORMER OWNER: 9222-9129 QUEBEC INC.

Effective date: 20110111

C41 Transfer of patent application or patent right or utility model
TA01 Transfer of patent application right

Effective date of registration: 20110111

Address after: Quebec

Applicant after: 7503547 Canada Company

Address before: Quebec

Applicant before: 9222-9129 Quebec Corporation

C14 Grant of patent or utility model
GR01 Patent grant
REG Reference to a national code

Ref country code: HK

Ref legal event code: GR

Ref document number: 1142597

Country of ref document: HK

CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20141210

Termination date: 20210312