EE03487B1 - 5-fenüül-3-(piperidin-4-üül)-1,3,4-oksadiasol-2(3H)-ooni derivaadid kasutamiseks 5-HT4 - või H3- retseptorite ligandidena - Google Patents

5-fenüül-3-(piperidin-4-üül)-1,3,4-oksadiasol-2(3H)-ooni derivaadid kasutamiseks 5-HT4 - või H3- retseptorite ligandidena

Info

Publication number
EE03487B1
EE03487B1 EE9800155A EE9800155A EE03487B1 EE 03487 B1 EE03487 B1 EE 03487B1 EE 9800155 A EE9800155 A EE 9800155A EE 9800155 A EE9800155 A EE 9800155A EE 03487 B1 EE03487 B1 EE 03487B1
Authority
EE
Estonia
Prior art keywords
oxadiazol
piperidin
ligands
receptors
phenyl
Prior art date
Application number
EE9800155A
Other languages
English (en)
Estonian (et)
Other versions
EE9800155A (et
Inventor
Jegham Samir
Lochead Alistair
Galli Fr�d�ric
Nedelec Alain
Solignac Axelle
De Cruz Laurence
Original Assignee
Synthlabo
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 claimed from FR9513253A external-priority patent/FR2741070B1/fr
Priority claimed from FR9513252A external-priority patent/FR2741069B1/fr
Priority claimed from FR9602663A external-priority patent/FR2745574B1/fr
Application filed by Synthlabo filed Critical Synthlabo
Publication of EE9800155A publication Critical patent/EE9800155A/xx
Publication of EE03487B1 publication Critical patent/EE03487B1/xx

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • A61P27/06Antiglaucoma agents or miotics
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/06Antiarrhythmics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth 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)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Psychiatry (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Psychology (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
EE9800155A 1995-11-09 1996-11-05 5-fenüül-3-(piperidin-4-üül)-1,3,4-oksadiasol-2(3H)-ooni derivaadid kasutamiseks 5-HT4 - või H3- retseptorite ligandidena EE03487B1 (et)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR9513253A FR2741070B1 (fr) 1995-11-09 1995-11-09 Derives de 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3h) -one, leur preparation et leur application en therapeutique
FR9513252A FR2741069B1 (fr) 1995-11-09 1995-11-09 Derives de 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3h) -one, leur preparation et leur application en therapeutique
FR9602663A FR2745574B1 (fr) 1996-03-04 1996-03-04 Derives de 5-phenyl-3-(piperidin-4-yl)-1, 3, 4-oxadiazol-2 (3h)-one, leur preparation et leur application en therapeutique
PCT/FR1996/001730 WO1997017345A1 (fr) 1995-11-09 1996-11-05 Derives de 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3h)-one, utiles comme ligands des recepteurs 5-ht4 ou h¿3?

Publications (2)

Publication Number Publication Date
EE9800155A EE9800155A (et) 1998-12-15
EE03487B1 true EE03487B1 (et) 2001-08-15

Family

ID=27253120

Family Applications (1)

Application Number Title Priority Date Filing Date
EE9800155A EE03487B1 (et) 1995-11-09 1996-11-05 5-fenüül-3-(piperidin-4-üül)-1,3,4-oksadiasol-2(3H)-ooni derivaadid kasutamiseks 5-HT4 - või H3- retseptorite ligandidena

Country Status (29)

Country Link
US (1) US5929089A (enExample)
EP (1) EP0863897B1 (enExample)
JP (1) JP4263240B2 (enExample)
CN (1) CN1077891C (enExample)
AR (1) AR004708A1 (enExample)
AT (1) ATE181328T1 (enExample)
AU (1) AU707325B2 (enExample)
BG (1) BG63463B1 (enExample)
BR (1) BR9611311A (enExample)
CA (1) CA2236357C (enExample)
CO (1) CO4770968A1 (enExample)
CZ (1) CZ287268B6 (enExample)
DE (1) DE69602970T2 (enExample)
EE (1) EE03487B1 (enExample)
ES (1) ES2135934T3 (enExample)
GR (1) GR3030823T3 (enExample)
HU (1) HUP0001168A3 (enExample)
IL (1) IL124364A (enExample)
MX (1) MX9803696A (enExample)
NO (1) NO309606B1 (enExample)
NZ (1) NZ321626A (enExample)
PL (1) PL186204B1 (enExample)
RU (1) RU2167160C2 (enExample)
SI (1) SI0863897T1 (enExample)
SK (1) SK282335B6 (enExample)
TR (1) TR199800827T2 (enExample)
TW (1) TW371303B (enExample)
UA (1) UA50748C2 (enExample)
WO (1) WO1997017345A1 (enExample)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW467902B (en) * 1996-07-31 2001-12-11 Bristol Myers Squibb Co Diphenyl heterocycles as potassium channel modulators
FR2762316B1 (fr) * 1997-04-18 1999-12-17 Sanofi Synthelabo Derives de 5-aryl-3-(8-azabicyclo[3.2.1] octan-3-yl)-1,3,4- oxadiazol-2(3h)-one, leur preparation et leur application en therapeutique
FR2763068B1 (fr) * 1997-05-06 1999-06-04 Synthelabo Derives de 3-(pyrrolidin-3-yl)-1,3,4-oxadiazol-2(3h)-one, leur preparation et leur application en therapeutique
AU7658798A (en) * 1997-05-06 1998-11-27 Synthelabo 5-phenyl-1,3,4-oxadiazol-2(3h)-one derivatives and their use as 5-ht4 ligands
GB9715816D0 (en) * 1997-07-25 1997-10-01 Black James Foundation Histamine H receptor ligands
US6960579B1 (en) 1998-05-19 2005-11-01 Alcon Manufacturing, Ltd. Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders
ES2252978T3 (es) 1998-09-18 2006-05-16 Alcon Manufacturing Ltd. Agonistas 5ht2 serotonergicos para tratar el glaucoma.
CN1461216A (zh) * 1999-04-28 2003-12-10 呼吸器有限公司 用作治疗有关支气管收缩的机能障碍的药物的化合物
JP2003501462A (ja) * 1999-06-15 2003-01-14 レスピラトリウス アクチボラゲット 受容体アゴニストおよびアンタゴニスト
CZ2003686A3 (cs) * 2000-08-08 2003-08-13 Ortho Mcneil Pharmaceutical, Inc. Neimidazolové aryloxypiperidiny
MXPA03001267A (es) 2000-08-08 2004-07-30 Johnson & Johnson Ariloxialquilaminas sin imidazol.
PT1311499E (pt) 2000-08-08 2006-07-31 Ortho Mcneil Pharm Inc Compostos biciclicos como ligandos do receptor h3
US7208497B2 (en) 2001-07-02 2007-04-24 Novo Nordisk A/S Substituted piperazines and diazepanes
ATE449090T1 (de) 2001-07-02 2009-12-15 High Point Pharmaceuticals Llc Substituierte piperazin- und diazepanderivate zur verwendung als histamin h3 rezeptormodulatoren
US6673829B2 (en) 2001-09-14 2004-01-06 Novo Nordisk A/S Aminoazetidine,-pyrrolidine and -piperidine derivatives
EP1434765B1 (en) * 2001-09-14 2009-12-02 High Point Pharmaceuticals, LLC Substituted piperidines with selective binding to histamine h3-receptor
JP4619655B2 (ja) 2001-09-14 2011-01-26 ハイ・ポイント・ファーマスーティカルズ、エルエルシー 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
US20030186963A1 (en) 2001-09-14 2003-10-02 Dorwald Florencio Zaragoza Substituted piperidines
US7064135B2 (en) 2001-10-12 2006-06-20 Novo Nordisk Inc. Substituted piperidines
WO2003031432A1 (en) 2001-10-12 2003-04-17 Novo Nordisk A/S Substituted piperidines and their use for the treatment of diseases related to the histamine h3 receptor
US7005448B2 (en) 2001-12-14 2006-02-28 Alcon, Inc. Aminoalkyl-benzofuran-5-ol compounds for the treatment of glaucoma
US20030236259A1 (en) * 2002-02-05 2003-12-25 Rolf Hohlweg Novel aryl- and heteroarylpiperazines
GB0211230D0 (en) 2002-05-16 2002-06-26 Medinnova Sf Treatment of heart failure
US7332508B2 (en) * 2002-12-18 2008-02-19 Novo Nordisk A/S Substituted homopiperidine, piperidine or pyrrolidine derivatives
GB0325956D0 (en) * 2003-11-06 2003-12-10 Addex Pharmaceuticals Sa Novel compounds
EA010891B9 (ru) 2004-06-15 2012-08-30 Пфайзер Инк. Производные бензимидазолонкарбоновой кислоты
US7737163B2 (en) 2004-06-15 2010-06-15 Pfizer Inc. Benzimidazolone carboxylic acid derivatives
EP2386554A1 (en) * 2005-07-04 2011-11-16 High Point Pharmaceuticals, LLC Compounds active at the histamine H3 receptor
RU2396269C2 (ru) * 2005-12-01 2010-08-10 Ф.Хоффманн-Ля Рош Аг Производные гетероарилзамещенного пиперидина в качестве ингибиторов печеночной карнитин пальмитоилтрансферазы (l-cpt1)
MX2008014766A (es) * 2006-05-29 2009-03-06 High Point Pharmaceuticals Llc 3-(1,3-benzodioxol-5-il)-6-(4-ciclopropilpiperazin-1-il)-piperazi na, sus sales y solvatos y su uso como antagonista del receptor de h3 histamina.
EP2014656A3 (en) * 2007-06-11 2011-08-24 High Point Pharmaceuticals, LLC New heteocyclic h3 antagonists
ME02107B (me) 2011-09-19 2015-10-20 Heteroaril jedinjenja kao ligandi 5-ht4 receptora

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5055476A (en) * 1990-08-13 1991-10-08 Hoechst-Roussel Pharmaceuticals Incorporated 3-(1,2-benzisoxazol-3-yl)-4-pyridinamines and derivatives
AU2435092A (en) * 1991-08-20 1993-03-16 Smithkline Beecham Plc 5-ht4 receptor antagonists
CA2118812C (en) * 1991-09-12 2006-01-17 Francis David King 5-ht4 receptor antagonists
CA2129112A1 (en) * 1992-02-06 1993-08-19 Francis David King Benzopyran, benzothiopyran and benzofuran derivatives as 5-ht4 antagonists
GB9219163D0 (en) * 1992-09-10 1992-10-28 Smithkline Beecham Plc Pharmaceuticals
JPH06157518A (ja) * 1992-11-27 1994-06-03 Yamanouchi Pharmaceut Co Ltd 新規なオキサジアゾール誘導体又はその塩

Also Published As

Publication number Publication date
NO309606B1 (no) 2001-02-26
TW371303B (en) 1999-10-01
PL186204B1 (pl) 2003-11-28
PL326671A1 (en) 1998-10-12
IL124364A (en) 2001-08-08
AR004708A1 (es) 1999-03-10
BG63463B1 (bg) 2002-02-28
CA2236357C (en) 2006-10-17
MX9803696A (es) 1998-09-30
WO1997017345A1 (fr) 1997-05-15
ATE181328T1 (de) 1999-07-15
CN1077891C (zh) 2002-01-16
AU707325B2 (en) 1999-07-08
UA50748C2 (uk) 2002-11-15
NZ321626A (en) 1998-10-28
EE9800155A (et) 1998-12-15
AU7500196A (en) 1997-05-29
TR199800827T2 (xx) 1999-02-22
GR3030823T3 (en) 1999-11-30
CZ287268B6 (en) 2000-10-11
JP2000500125A (ja) 2000-01-11
NO982092D0 (no) 1998-05-07
SI0863897T1 (en) 1999-10-31
BG102412A (en) 1999-08-31
CO4770968A1 (es) 1999-04-30
RU2167160C2 (ru) 2001-05-20
IL124364A0 (en) 1998-12-06
SK59998A3 (en) 1998-11-04
ES2135934T3 (es) 1999-11-01
EP0863897A1 (fr) 1998-09-16
HUP0001168A3 (en) 2001-07-30
CZ142198A3 (cs) 1998-08-12
DE69602970D1 (de) 1999-07-22
DE69602970T2 (de) 2000-01-20
BR9611311A (pt) 1999-06-29
HUP0001168A2 (hu) 2001-04-28
JP4263240B2 (ja) 2009-05-13
CN1202169A (zh) 1998-12-16
CA2236357A1 (en) 1997-05-15
US5929089A (en) 1999-07-27
SK282335B6 (sk) 2002-01-07
HK1016165A1 (en) 1999-10-29
EP0863897B1 (fr) 1999-06-16
NO982092L (no) 1998-06-29

Similar Documents

Publication Publication Date Title
EE03487B1 (et) 5-fenüül-3-(piperidin-4-üül)-1,3,4-oksadiasol-2(3H)-ooni derivaadid kasutamiseks 5-HT4 - või H3- retseptorite ligandidena
FI973205A7 (fi) Indolijohdannaisia 5-HT-reseptoriantagonisteina
ATE201016T1 (de) Pyrimidindion-, pyrimidintrion-, triazindion- derivate als alpha-1-adrenergische rezeptorantagonisten
DK0920438T3 (da) N6-heterocyklisk-substituerede adenosinderivater
FR2637796B1 (fr) Charniere pour abattant de w.c.
DE69801905D1 (de) 5-aryl-3-(8-azabicyclo[3.2.1]oct-3-yl)-1,3,4-oxadiazol-2(3h)-one derivate als 5-ht4 rezeptor liganden
KR970013921U (ko) 건축용 다용도 브라켓
NO308035B1 (no) Substituerte tetracykliske azepinderivater som har affinitet for 5-HT2-reseptorer
MA23795A1 (fr) Derives d'indole substitues
AU7578396A (en) Substituted tetrahydropyridine derivatives acting on 5-ht receptors
DK0863897T3 (da) Derivater af 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3H)-on, som kan anvendes som ligander for 5-HT4- eller H3-recept
BR9510036A (pt) Derivados de 1,3,4-oxadiazina
ZA9600758D (en) Idole derivatives as 5-ht receptor antagonist.
FR2741070B1 (fr) Derives de 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3h) -one, leur preparation et leur application en therapeutique
AU7658898A (en) 3-(pyrrolidin-3-yl)-1,3,4-oxadiazol-2(3h)-one derivatives and their use as 5-ht4ligands
FR2745574B1 (fr) Derives de 5-phenyl-3-(piperidin-4-yl)-1, 3, 4-oxadiazol-2 (3h)-one, leur preparation et leur application en therapeutique
KR960013523U (ko) 내경 조절용 보링 바
FR2759699B1 (fr) Derives de 5-(2,3-dihydro-1,4-benzoxazin-5-yl)-3-(piperidin- 4-yl)-1,3,4-oxadiazol-2(3h)-one, leur preparation et leur application en therapeutique
DK1133494T3 (da) 8-Azabicyclo[3.2.1]oct-2-en-derivater
IT232910Y1 (it) supporto per strumenti odontoiatrici accessori.

Legal Events

Date Code Title Description
KB4A Valid patent at the end of a year

Effective date: 20021231

KB4A Valid patent at the end of a year

Effective date: 20031231

HC1A Change of owner name
KB4A Valid patent at the end of a year

Effective date: 20041231

KB4A Valid patent at the end of a year

Effective date: 20051231

KB4A Valid patent at the end of a year

Effective date: 20061231

KB4A Valid patent at the end of a year

Effective date: 20071231

KB4A Valid patent at the end of a year

Effective date: 20081231

KB4A Valid patent at the end of a year

Effective date: 20091231

KB4A Valid patent at the end of a year

Effective date: 20101231

MM4A Lapsed by not paying the annual fees

Effective date: 20131105