JP4607458B2 - 新規なアリールおよびへテロアリールピペラジン - Google Patents

新規なアリールおよびへテロアリールピペラジン Download PDF

Info

Publication number
JP4607458B2
JP4607458B2 JP2003565978A JP2003565978A JP4607458B2 JP 4607458 B2 JP4607458 B2 JP 4607458B2 JP 2003565978 A JP2003565978 A JP 2003565978A JP 2003565978 A JP2003565978 A JP 2003565978A JP 4607458 B2 JP4607458 B2 JP 4607458B2
Authority
JP
Japan
Prior art keywords
alkyl
compound
aryl
alkoxy
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
JP2003565978A
Other languages
English (en)
Japanese (ja)
Other versions
JP2005533747A (ja
Inventor
ホールウェグ、ロルフ
デルバルト、フロレンシオ・ザラゴザ
スティーブンセン、ヘンリク
ペッターソン、イングリド
ペシュケ、ベルンド
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.)
vTv Therapeutics LLC
Original Assignee
High Point Pharnaceuticals LLC
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 High Point Pharnaceuticals LLC filed Critical High Point Pharnaceuticals LLC
Publication of JP2005533747A publication Critical patent/JP2005533747A/ja
Application granted granted Critical
Publication of JP4607458B2 publication Critical patent/JP4607458B2/ja
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon 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
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic 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
    • 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
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Diabetes (AREA)
  • Biomedical Technology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Immunology (AREA)
  • Hospice & Palliative Care (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pulmonology (AREA)
  • Psychiatry (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Pyridine Compounds (AREA)
JP2003565978A 2002-02-05 2003-02-05 新規なアリールおよびへテロアリールピペラジン Expired - Fee Related JP4607458B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DKPA200200168 2002-02-05
US35663002P 2002-02-08 2002-02-08
US39930402P 2002-07-26 2002-07-26
DKPA200201142 2002-07-26
PCT/DK2003/000071 WO2003066604A2 (en) 2002-02-05 2003-02-05 Novel aryl- and heteroarylpiperazines

Publications (2)

Publication Number Publication Date
JP2005533747A JP2005533747A (ja) 2005-11-10
JP4607458B2 true JP4607458B2 (ja) 2011-01-05

Family

ID=27739216

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2003565978A Expired - Fee Related JP4607458B2 (ja) 2002-02-05 2003-02-05 新規なアリールおよびへテロアリールピペラジン

Country Status (12)

Country Link
EP (1) EP1474401A2 (de)
JP (1) JP4607458B2 (de)
CN (1) CN1628109A (de)
AU (2) AU2003203148A1 (de)
BR (1) BR0307429A (de)
CA (1) CA2474214A1 (de)
IL (1) IL162859A0 (de)
MX (1) MXPA04007612A (de)
NO (1) NO328714B1 (de)
PL (1) PL372390A1 (de)
WO (1) WO2003066604A2 (de)
ZA (1) ZA200405694B (de)

Families Citing this family (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7390813B1 (en) 2001-12-21 2008-06-24 Xenon Pharmaceuticals Inc. Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents
GB0224084D0 (en) 2002-10-16 2002-11-27 Glaxo Group Ltd Novel compounds
US7279491B2 (en) 2002-10-23 2007-10-09 Janssen Pharmaceutica N.V. Phenylpiperidines and phenylpyrrolidines
KR20060054392A (ko) * 2003-07-29 2006-05-22 노보 노르디스크 에이/에스 피리다지닐-피페라진 및 히스타민 ｈ３ 수용체 리간드로서그들의 사용
US7754711B2 (en) * 2003-07-30 2010-07-13 Xenon Pharmaceuticals Inc. Pyridazine derivatives and their use as therapeutic agents
SG145700A1 (en) 2003-07-30 2008-09-29 Xenon Pharmaceuticals Inc Pyridyl derivatives and their use as therapeutic agents
EP2316827B1 (de) 2003-07-30 2016-01-27 Xenon Pharmaceuticals Inc. Piperazin derivate und deren anwendung als therapeutische wirkstoffe
SG145699A1 (en) * 2003-07-30 2008-09-29 Xenon Pharmaceuticals Inc Pyridazine derivatives and their use as therapeutic agents
WO2005035521A1 (en) * 2003-10-09 2005-04-21 Argenta Discovery Ltd. Substituted quinolines as mcr modulators
GB0324159D0 (en) 2003-10-15 2003-11-19 Glaxo Group Ltd Novel compounds
JP4596792B2 (ja) * 2004-02-24 2010-12-15 あすか製薬株式会社 ５−ｈｔ１ａ作動作用と５−ｈｔ３拮抗作用を併有する薬剤
MXPA06011414A (es) 2004-03-31 2007-04-20 Johnson & Johnson Compuestos heterociclicos sin imidazol como ligandos del receptor de h3 histamina.
US20080125403A1 (en) 2004-04-02 2008-05-29 Merck & Co., Inc. Method of Treating Men with Metabolic and Anthropometric Disorders
US20050256309A1 (en) * 2004-05-12 2005-11-17 Altenbach Robert J Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands
CA2571555A1 (en) * 2004-06-22 2006-01-05 Pfizer Products Inc. Diazabicyclic histamine-3 receptor antagonists
CN101090724A (zh) * 2004-09-20 2007-12-19 泽农医药公司 用于抑制人硬脂酰CoA去饱和酶的吡啶衍生物
CN101084212A (zh) 2004-09-20 2007-12-05 泽农医药公司 杂环衍生物及其作为硬脂酰CoA去饱和酶介导剂的用途
CN101083986A (zh) 2004-09-20 2007-12-05 泽农医药公司 双环杂环衍生物及其作为硬脂酰CoA去饱和酶(SCD)抑制剂的用途
CN101084207A (zh) 2004-09-20 2007-12-05 泽农医药公司 杂环衍生物及其作为硬脂酰CoA去饱和酶抑制剂的用途
WO2006034279A1 (en) 2004-09-20 2006-03-30 Xenon Pharmaceuticals Inc. Heterocyclic derivatives and their use as therapeutic agents
CA2580857A1 (en) 2004-09-20 2006-09-28 Xenon Pharmaceuticals Inc. Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors
AU2005286793A1 (en) 2004-09-20 2006-03-30 Xenon Pharmaceuticals Inc. Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-CoA desaturase enzymes
JP5149009B2 (ja) 2004-09-20 2013-02-20 ゼノン・ファーマシューティカルズ・インコーポレイテッド ヒトステアロイル−ＣｏＡデサチュラーゼを阻害するためのピリダジン誘導体
EP1807085B1 (de) 2004-09-20 2013-08-21 Xenon Pharmaceuticals Inc. Heterozyklische Derivate und ihre Verwendung als Stearoyl-Coa-Desaturase-Inhibitoren
EP2592075B1 (de) * 2004-11-02 2015-04-29 Northwestern University Pyridazinverbindungen zur behandlung von entzündlichen erkrankungen
US7700595B2 (en) 2005-03-01 2010-04-20 Wyeth Llc Cinnoline compounds
AU2006343359A1 (en) 2005-06-03 2007-11-15 Xenon Pharmaceuticals Inc. Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors
JP5121707B2 (ja) 2005-07-04 2013-01-16 ハイ ポイント ファーマシューティカルズ，エルエルシー 新規医薬
PT1904455E (pt) * 2005-07-05 2011-10-04 Hoffmann La Roche Derivados de piridazina
EP1917245A1 (de) 2005-08-21 2008-05-07 Abbott GmbH & Co. KG Heterocyclische verbindungen und ihre verwendung als bindungspartner für 5-ht5-rezeptoren
GB0517184D0 (en) * 2005-08-22 2005-09-28 Glaxo Group Ltd Compounds
DE602006013501D1 (de) 2005-09-16 2010-05-20 Janssen Pharmaceutica Nv Cyclopropylamine als modulatoren des histamin-h3-rezeptors
JO2769B1 (en) 2005-10-26 2014-03-15 جانسين فارماسوتيكا ان. في Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor
SG170785A1 (en) * 2006-03-28 2011-05-30 Transtech Pharma Benzothiazoles having histamine h3 receptor activity
CN101754762A (zh) * 2006-04-28 2010-06-23 西北大学 用于治疗神经炎症性疾病的包含哒嗪化合物的制剂
JP2009537596A (ja) 2006-05-23 2009-10-29 ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー ６−（４−シクロプロピルピペリジン−１−イル）−２’−メチル−［３，４’］−ビピリジン及びその医薬としての使用
SI2079732T1 (sl) * 2006-05-29 2012-03-30 High Point Pharmaceuticals Llc benzodioksol il ciklopropilpiperazin il piridazin njegove soli in solvati in njegova uporaba kot antagonist histaminskega receptorja H
WO2007137955A1 (en) * 2006-05-30 2007-12-06 F. Hoffmann-La Roche Ag Piperidinyl pyrimidine derivatives
MY146506A (en) 2006-05-30 2012-08-15 Janssen Pharmaceutica Nv Substituted pyridyl amide compounds as modulators of the histamine h3 receptor
US9108948B2 (en) 2006-06-23 2015-08-18 Abbvie Inc. Cyclopropyl amine derivatives
AU2007260836B2 (en) 2006-06-23 2012-11-15 Abbvie Bahamas Ltd. Cyclopropyl amine derivatives as histamin H3 receptor modulators
WO2008003702A2 (en) * 2006-07-03 2008-01-10 Vereniging Voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek En Patientenzorg Fused bicyclic compounds interacting with the histamine h4 receptor
JO2642B1 (en) 2006-12-08 2012-06-17 جانسين فارماسوتيكا ان. في Dopamine 2 receptor antagonists are rapidly hydrolyzed
JO2849B1 (en) * 2007-02-13 2015-03-15 جانسين فارماسوتيكا ان. في Dopamine 2 receptor antagonists are rapidly hydrolyzed
RU2489431C2 (ru) 2007-04-23 2013-08-10 Янссен Фармацевтика Н.В. Тиа(диа)золы как быстро диссоциирующие антагонисты рецептора допамина 2
RS52518B (sr) 2007-04-23 2013-04-30 Janssen Pharmaceutica N.V. Derivati 4-alkoksipiridazina kao brzo disocirajući dopamin 2 receptorski antagonisti
CA2687931C (en) * 2007-05-31 2016-05-24 Boehringer Ingelheim International Gmbh Ccr2 receptor antagonists and uses thereof
EP2014656A3 (de) * 2007-06-11 2011-08-24 High Point Pharmaceuticals, LLC Neue heterocyclische H3-Antagonisten
CA2695071A1 (en) * 2007-08-02 2009-02-05 F. Hoffmann-La Roche Ag The use of benzamide derivatives for the treatment of cns disorders
KR20100059944A (ko) 2007-09-06 2010-06-04 글락소 그룹 리미티드 히스타민 ｈ３ 수용체에 대해 친화성을 갖는 피페라진 유도체
BRPI0820481A2 (pt) 2007-11-20 2015-06-16 Janssen Pharmaceutica Nv Composotos cicloalquilóxi e heterocicloalquilóxi piridina como moduladores do receptor de h3 de histamina
US20120015957A1 (en) * 2007-12-17 2012-01-19 Wenying Chai Piperazinyl derivatives useful as modulators of the neuropeptide y2 receptor
WO2009079597A1 (en) * 2007-12-17 2009-06-25 Janssen Pharmaceutica N.V. Piperazinyl derivatives useful as modulators of the neuropeptide y2 receptor
JP5417439B2 (ja) 2008-07-03 2014-02-12 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ ５−ｈｔ６受容体アンタゴニストとしての置換された６−（１−ピペラジニル）−ピリダジン類
LT2307374T (lt) 2008-07-31 2017-04-25 Janssen Pharmaceutica Nv Piperazin-1-il-trifluormetil-pakeistieji piridinai kaip greitai disocijuojantys dopamino 2 receptoriaus antagonistai
PL2379525T3 (pl) 2008-12-19 2016-01-29 Centrexion Therapeutics Corp Cykliczne pirymidyno-4-karboksamidy jako antagoniści receptora CCR2 do leczenia stanów zapalnych, astmy oraz COPD
US9186353B2 (en) 2009-04-27 2015-11-17 Abbvie Inc. Treatment of osteoarthritis pain
AU2010332969B2 (en) 2009-12-17 2015-02-12 Centrexion Therapeutics Corporation New CCR2 receptor antagonists and uses thereof
WO2011103091A1 (en) 2010-02-18 2011-08-25 Transtech Pharma, Inc. Phenyl-heteroaryl derivatives and methods of use thereof
WO2011141474A1 (en) 2010-05-12 2011-11-17 Boehringer Ingelheim International Gmbh Novel ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments
JP5646736B2 (ja) 2010-05-12 2014-12-24 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 新規ｃｃｒ２受容体アンタゴニスト、これらの製造方法、及び薬物としてのこれらの使用
EP2571870B1 (de) 2010-05-17 2015-01-21 Boehringer Ingelheim International GmbH Ccr2-antagonisten und verwendungen dafür
WO2011147772A1 (en) 2010-05-25 2011-12-01 Boehringer Ingelheim International Gmbh Ccr2 receptor antagonists
US8962656B2 (en) 2010-06-01 2015-02-24 Boehringer Ingelheim International Gmbh CCR2 antagonists
US8853390B2 (en) 2010-09-16 2014-10-07 Abbvie Inc. Processes for preparing 1,2-substituted cyclopropyl derivatives
JP5786258B2 (ja) 2011-07-15 2015-09-30 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 新規かつ選択的なｃｃｒ２拮抗薬
WO2013151982A1 (en) 2012-04-03 2013-10-10 Arena Pharmaceuticals, Inc. Methods and compounds useful in treating pruritus, and methods for identifying such compounds
PL3177612T3 (pl) 2014-08-04 2022-08-08 Nuevolution A/S Opcjonalnie skondensowane pochodne pirymidyny podstawione heterocyklilem, użyteczne w leczeniu chorób zapalnych, metabolicznych, onkologicznych i autoimmunologicznych
CA2990460C (en) 2015-07-02 2023-10-17 Centrexion Therapeutics Corporation (4-((3r,4r)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2r,6s)-6-(p-tolyl)tetrahydro-2h-pyran-2-yl)methylamino)pyrimidin-4-yl)methanone citrate
NZ786543A (en) 2019-12-20 2026-01-30 Nuevolution As Compounds active towards nuclear receptors
US11447479B2 (en) 2019-12-20 2022-09-20 Nuevolution A/S Compounds active towards nuclear receptors
CA3174252A1 (en) 2020-03-31 2021-10-07 Nuevolution A/S Compounds active towards nuclear receptors
CA3174176A1 (en) 2020-03-31 2021-10-07 Sanne Schroder Glad Compounds active towards nuclear receptors

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB753166A (en) * 1953-05-22 1956-07-18 Miles Lab Improvements in or relating to substituted piperazines
US2993899A (en) * 1958-03-31 1961-07-25 Miles Lab Acetylenically unsaturated piperazine derivatives
US3309370A (en) * 1964-07-16 1967-03-14 Miles Lab Bicycloalkyl piperazine derivatives and process
FR2306694A1 (fr) * 1975-04-07 1976-11-05 Parcor Derives de la piperazine
US4144346A (en) * 1977-01-31 1979-03-13 Janssen Pharmaceutica N.V. Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
US4163849A (en) * 1978-03-17 1979-08-07 Merck & Co., Inc. Piperazinylpyrazines
JPS56118074A (en) * 1980-02-22 1981-09-16 Tanabe Seiyaku Co Ltd Propane derivative and its preparation
US4339579A (en) * 1980-12-29 1982-07-13 American Home Products Corporation 2,6-Bis-(pyrrolopyrazinyl)pyrazines
US5001125A (en) * 1984-03-26 1991-03-19 Janssen Pharmaceutica N.V. Anti-virally active pyridazinamines
FR2573075B1 (fr) * 1984-09-14 1987-03-20 Innothera Lab Sa Nouvelles (pyridyl-2)-1 piperazines, leur procede de preparation et leur application en therapeutique
JP2576862B2 (ja) * 1986-03-05 1997-01-29 大塚製薬 株式会社 カルボスチリル誘導体
DK111387A (da) * 1986-03-05 1987-09-06 Otsuka Pharma Co Ltd Carbostyrilderivater og salte deraf, laegemiddel indeholdende saadanne derivater samt fremgangsmaade til fremstilling af derivaterne
AU639529B2 (en) * 1987-03-04 1993-07-29 Higuchi, Yoshinari Carbostyril derivatives and salts thereof and anti-arrhythmic agents containing the carbostyril derivatives
DE3803860A1 (de) * 1988-02-09 1989-08-17 Basf Ag N,n'-disubstituierte piperazine
ATE107922T1 (de) * 1989-03-03 1994-07-15 Dainippon Pharmaceutical Co 2-(1-piperazinyl)-4-phenylcycloalkanpyridin- derivate, verfahren zu deren herstellung und pharmazeutische zusammensetzungen, die sie enthalten.
GB9012316D0 (en) * 1990-06-01 1990-07-18 Wellcome Found Pharmacologically active cns compounds
WO1997002245A1 (en) * 1995-07-06 1997-01-23 Japan Tobacco Inc. Benzamidoxime derivatives and medicinal use thereof
JPH0971564A (ja) * 1995-07-06 1997-03-18 Japan Tobacco Inc ベンズアミドオキシム誘導体及びその医薬用途
DZ2376A1 (fr) * 1996-12-19 2002-12-28 Smithkline Beecham Plc Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant.
DE69839887D1 (de) * 1997-10-02 2008-09-25 Eisai R&D Man Co Ltd Kondensierte pyridinderivate
JP3989102B2 (ja) * 1997-10-02 2007-10-10 エーザイ・アール・アンド・ディー・マネジメント株式会社 縮合ピリジン誘導体
AU2935200A (en) * 1999-04-30 2000-11-17 Pfizer Products Inc. Compounds for the treatment of obesity
GB9926303D0 (en) * 1999-11-05 2000-01-12 Smithkline Beecham Plc Novel compounds
GB9926302D0 (en) * 1999-11-05 2000-01-12 Smithkline Beecham Plc Novel compounds
AU2261401A (en) * 1999-12-16 2001-06-25 Schering Corporation Substituted imidazole neuropeptide y y5 receptor antagonists
FI20000480A0 (fi) * 2000-03-01 2000-03-01 Orion Yhtymae Oyj Kinoliini- ja naftaleenijohdannaisia alfa-2 antagonisteina
CN101406469B (zh) * 2001-01-31 2012-06-13 H·隆德贝克有限公司 Gal3受体拮抗剂在治疗抑郁和/或焦虑中的应用及在这种方法中有用的化合物
AU2003229535A1 (en) * 2002-06-06 2003-12-22 Novo Nordisk A/S Substituted hexahydropyrrolo(1,2-a)pyrazines, octahydropyrido(1,2-a)pyrazines and decahydropyrazino(1,2-a)azepines

Also Published As

Publication number Publication date
NO328714B1 (no) 2010-05-03
BR0307429A (pt) 2004-12-28
IL162859A0 (en) 2005-11-20
NO20043709L (no) 2004-09-03
PL372390A1 (en) 2005-07-25
JP2005533747A (ja) 2005-11-10
MXPA04007612A (es) 2004-11-10
WO2003066604A2 (en) 2003-08-14
AU2003203148A1 (en) 2003-09-02
WO2003066604A3 (en) 2003-12-04
ZA200405694B (en) 2005-09-28
EP1474401A2 (de) 2004-11-10
CN1628109A (zh) 2005-06-15
CA2474214A1 (en) 2003-08-14
AU2010200135A1 (en) 2010-02-04

Similar Documents

Publication Publication Date Title
JP4607458B2 (ja) 新規なアリールおよびへテロアリールピペラジン
US20090264435A1 (en) Novel Aryl- and Heteroarylpiperazines
CA2532236C (en) Pyridazinyl- piperazines and their use as histamine h3 receptor ligands
TW591022B (en) Tetrahydropyridino or piperidino heterocyclic derivatives
JP6259463B2 (ja) ＩＬ−１２、ＩＬ−２３および／またはＩＦＮα応答のモジュレーターとして有用であるアルキルアミド置換ピリジル化合物
US8163756B2 (en) Enzyme modulators and treatments
KR970005927B1 (ko) 디아릴메틸피페리딘 또는 피페라진의 피리딘 및 피리딘 n-옥사이드 유도체, 이를 함유하는 약제학적 조성물 및 이의 제조방법
JP4619655B2 (ja) 新規アミノアゼチジン、−ピロリジンおよび−ピペリジン誘導体
US20070213338A1 (en) Triazolo-Pyridazine Compounds and Derivatives Thereof Useful in the Treatment of Neuropathic Pain
JP4918477B2 (ja) １−アミノ−フタラジン誘導体、これらの調製及び治療的使用
HUP0201406A2 (en) Aromatic heterocyclic compounds as antiinflammatory agents, process for their preparation and pharmaceutical compositions containing them
AU2003268447A1 (en) Pyrazolopyridines and method of making and using the same
CA2589777A1 (en) Compounds and compositions as modulators of steroidal receptors and calcium channel activities
JP2005529942A (ja) 置換ピラジン類および置換アゼピン類
JP6254194B2 (ja) ホスホジエステラーゼ１０阻害剤（ｐｄｅ−１０）としての新規ピリミジン誘導体
TW200404067A (en) New compounds
RU2361869C2 (ru) Новые арил- и гетероарилпиперазины
KR20040081177A (ko) 신규 아릴- 및 헤테로아릴피페라진
US7939520B2 (en) Aminoazacyclyl-3-sulfonylindazoles as 5-hydroxytryptamine-6 ligands
HK1143364A (en) Novel aryl-and heteroarylpiperazines
JP6622300B2 (ja) 新規なジヒドロキノリンピラゾリル化合物
JPWO2001043746A1 (ja) 医薬組成物

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20060111

A711 Notification of change in applicant

Free format text: JAPANESE INTERMEDIATE CODE: A711

Effective date: 20080616

A711 Notification of change in applicant

Free format text: JAPANESE INTERMEDIATE CODE: A711

Effective date: 20090326

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20090722

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20090728

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20091028

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20091105

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20100126

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20100330

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20100624

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20100907

A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20101007

R150 Certificate of patent or registration of utility model

Free format text: JAPANESE INTERMEDIATE CODE: R150

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20131015

Year of fee payment: 3

LAPS Cancellation because of no payment of annual fees