PE20071311A1 - Compuestos 8-azabiciclo[3.2.1]octano como antagonistas del receptor opioide mu - Google Patents
Compuestos 8-azabiciclo[3.2.1]octano como antagonistas del receptor opioide muInfo
- Publication number
- PE20071311A1 PE20071311A1 PE2007000212A PE2007000212A PE20071311A1 PE 20071311 A1 PE20071311 A1 PE 20071311A1 PE 2007000212 A PE2007000212 A PE 2007000212A PE 2007000212 A PE2007000212 A PE 2007000212A PE 20071311 A1 PE20071311 A1 PE 20071311A1
- Authority
- PE
- Peru
- Prior art keywords
- azabicycle
- alkyl
- compounds
- octane
- antagonists
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 239000005557 antagonist Substances 0.000 title abstract 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 title abstract 2
- 108020001612 μ-opioid receptors Proteins 0.000 title abstract 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 3
- -1 (S) -2,3-DIHYDROXY-PROPIONYL Chemical class 0.000 abstract 1
- 208000018522 Gastrointestinal disease Diseases 0.000 abstract 1
- 229910003827 NRaRb Inorganic materials 0.000 abstract 1
- 230000004064 dysfunction Effects 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 230000000968 intestinal effect Effects 0.000 abstract 1
- 102000051367 mu Opioid Receptors Human genes 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
- A61P1/10—Laxatives
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
REFERIDA A UN COMPUESTO 8-AZABICICLO[3.2.1]OCTANO DE FORMULA (I), DONDE R1 ES ORa, C(O)NRaRb, NHS(O)2Rc, CH2OH, ENTRE OTROS; A ES ALQUILENILO C1-C4; R2 ES CICLOALQUILO C3-C12 O ARILO C6-C10, OPCIONALMENTE SUSTITUIDOS CON ORa, HALO, ALQUILO C1-C3, ENTRE OTROS; G ES ALQUILENILO C1-C4; R3 ES H, C(O)R4, S(O)2Rc, ENTRE OTROS; R4 ES CICLOALQUILO C3-C6, ALQUILO C1-C6, ENTRE OTROS; Ra Y Rb SON H O ALQUILO C1-C4; Rc ES ALQUILO C1-C3. SON COMPUESTOS PREFERIDOS: 3-ENDO-(8-{2-[CICLOHEXILMETIL-(2-HIDROXIACETIL)-AMINO]ETIL}-8-AZABICICLO[3.2.1]OCT-3-IL)-BENZAMIDA, 3-ENDO-(8-{2.[BENCIL-(2-HIDROXIACETIL)-AMINO]ETIL}-8-AZABICICLO[3.2.1]OCT-3-IL)-BENZAMIDA, 3-ENDO-(8-{2-[CICLOHEXILMETIL-((S)-2,3-DIHIDROXI-PROPIONIL)AMINO]ETIL}-8-AZABICILO[3.2.1]OCT-3-IL)-BENZAMIDA, ENTRE OTROS. TAMBIEN ESTA REFERIDA A UNA COMPOSICION FARMACEUTICA. DICHOS COMPUESTOS SON ANTAGONISTAS DEL RECEPTOR OPIOIDE MU Y SON UTILES EN EL TRATAMIENTO DE TRASTORNOS GASTROINTESTINALES, DISFUNCION INTESTINAL INDUCIDA POR OIPIOIDES, ENTRE OTROS
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77796206P | 2006-03-01 | 2006-03-01 | |
| US84102806P | 2006-08-30 | 2006-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20071311A1 true PE20071311A1 (es) | 2007-12-29 |
Family
ID=38436795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2007000212A PE20071311A1 (es) | 2006-03-01 | 2007-02-28 | Compuestos 8-azabiciclo[3.2.1]octano como antagonistas del receptor opioide mu |
Country Status (24)
| Country | Link |
|---|---|
| US (11) | US7622508B2 (es) |
| EP (1) | EP2001876B1 (es) |
| JP (2) | JP5086280B2 (es) |
| KR (1) | KR101376479B1 (es) |
| AR (1) | AR059690A1 (es) |
| AT (1) | ATE509928T1 (es) |
| AU (1) | AU2007224213B2 (es) |
| BR (1) | BRPI0708490B8 (es) |
| CA (1) | CA2646409C (es) |
| CY (1) | CY1111747T1 (es) |
| DK (1) | DK2001876T3 (es) |
| HR (1) | HRP20110590T1 (es) |
| IL (1) | IL193690A (es) |
| MA (1) | MA30284B1 (es) |
| MX (1) | MX2008011165A (es) |
| MY (1) | MY145633A (es) |
| NZ (1) | NZ570764A (es) |
| PE (1) | PE20071311A1 (es) |
| PL (1) | PL2001876T3 (es) |
| PT (1) | PT2001876E (es) |
| RU (1) | RU2423362C2 (es) |
| SI (1) | SI2001876T1 (es) |
| TW (1) | TWI379832B (es) |
| WO (1) | WO2007103187A2 (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY145633A (en) * | 2006-03-01 | 2012-03-15 | Theravance Inc | 8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
| TWI409067B (zh) | 2007-02-28 | 2013-09-21 | Theravance Inc | 8-氮雜雙環〔3.2.1〕辛烷化合物之結晶型 |
| TWI415850B (zh) * | 2007-07-20 | 2013-11-21 | Theravance Inc | 製備mu類鴉片受體拮抗劑之中間物的方法 |
| EP2185553B1 (en) * | 2007-08-27 | 2012-06-27 | Theravance, Inc. | Amidoalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
| TWI423801B (zh) | 2007-08-27 | 2014-01-21 | Theravance Inc | 作為μ類鴉片受體拮抗劑之8-氮雜雙環〔3.2.1〕辛基-2-羥基苯甲醯胺化合物 |
| WO2009029253A1 (en) * | 2007-08-27 | 2009-03-05 | Theravance, Inc. | Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
| DE602008005771D1 (de) * | 2007-08-27 | 2011-05-05 | Theravance Inc | Disubstituierte alkyl-8-azabicycloä3.2.1üoktan-verbindungen als mu-opioid-rezeptorantagonisten |
| JP5797655B2 (ja) * | 2009-09-18 | 2015-10-21 | アドラー・コーポレーション | 消化管障害のためのオピオイド受容体アンタゴニストの使用 |
| US20120122928A1 (en) | 2010-08-11 | 2012-05-17 | Bayer Cropscience Ag | Heteroarylpiperidine and -Piperazine Derivatives as Fungicides |
| US8759527B2 (en) | 2010-08-25 | 2014-06-24 | Bayer Cropscience Ag | Heteroarylpiperidine and -piperazine derivatives as fungicides |
| EP2423210A1 (de) | 2010-08-25 | 2012-02-29 | Bayer CropScience AG | Heteroarylpiperidin- und -piperazinderivate als Fungizide |
| WO2012055837A1 (de) | 2010-10-27 | 2012-05-03 | Bayer Cropscience Ag | Heteroarylpiperidin und -piperazinderivate als fungizide |
| JP5703009B2 (ja) * | 2010-12-16 | 2015-04-15 | 住友精化株式会社 | スルホン化合物、スルホン化合物の製造方法、および電気化学デバイス用電解液 |
| WO2012104273A1 (de) | 2011-02-01 | 2012-08-09 | Bayer Cropscience Ag | Heteroarylpiperidin und -piperazinderivate als fungizide |
| WO2013037768A1 (de) | 2011-09-15 | 2013-03-21 | Bayer Intellectual Property Gmbh | Piperidinpyrazole als fungizide |
| EP2921481A1 (de) | 2011-12-27 | 2015-09-23 | Bayer Intellectual Property GmbH | 4-piperidine carboxylic acid derivatives |
| CA2875384A1 (en) | 2013-12-20 | 2015-06-20 | AntiOP, Inc. | Intranasal naloxone compositions and methods of making and using same |
| HRP20200432T1 (hr) | 2015-04-02 | 2020-06-12 | Theravance Biopharma R&D Ip, Llc | Oblik za kombinacijsko doziranje antagonista mu opioidnog receptora i opioidnog sredstva |
| MX2020008195A (es) | 2018-02-05 | 2020-11-24 | Alkermes Inc | Compuestos para el tratamiento del dolor. |
| KR20230154789A (ko) * | 2020-11-06 | 2023-11-09 | 액티노젠 메디컬 리미티드 | 헤테로고리 메탄온 화합물 및 그의 아자-비시클로 중간체의 제조 공정 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1067824B (de) * | 1954-10-20 | 1959-10-29 | Sandoz Ag | Verfahren zur Herstellung saeureamidartiger Tropanabkoemmlinge |
| US5159081A (en) | 1991-03-29 | 1992-10-27 | Eli Lilly And Company | Intermediates of peripherally selective n-carbonyl-3,4,4-trisubstituted piperidine opioid antagonists |
| UA58476C2 (uk) * | 1997-10-09 | 2003-08-15 | Санофі-Сентелябо | Похідні 8-азабіцикло[3.2.1]октан-3-метанаміну, фармацевтична композиція та лікарський засіб |
| US6900228B1 (en) | 1998-03-10 | 2005-05-31 | Research Triangle Institute | Opiate compounds, methods of making and methods of use |
| GB9810671D0 (en) | 1998-05-18 | 1998-07-15 | Pfizer Ltd | Anti-pruritic agents |
| TWI244481B (en) | 1998-12-23 | 2005-12-01 | Pfizer | 3-azabicyclo[3.1.0]hexane derivatives useful in therapy |
| GB9912410D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
| US6469030B2 (en) | 1999-11-29 | 2002-10-22 | Adolor Corporation | Methods for the treatment and prevention of ileus |
| US6552036B2 (en) | 2000-03-03 | 2003-04-22 | Ortho-Mcneil Pharmaceutical, Inc. | 3-(Diarylmethylene)-8-azabicyclo[3.2.1]octane derivatives |
| US20030181447A1 (en) * | 2001-02-22 | 2003-09-25 | Boyd Robert E. | 3-(Diarylmethylene)-8-azabicyclo[3.2.1]octane derivatives |
| US20020025948A1 (en) | 2000-06-23 | 2002-02-28 | Banks Bernard Joseph | 3-azabicyclo[3.1.0]hexane derivatives useful in therapy |
| JP4009251B2 (ja) | 2001-10-09 | 2007-11-14 | 杏林製薬株式会社 | 新規な4−(2−フロイル)アミノピペリジン、その合成中間体、その製造方法および医薬としてのその用途 |
| AP1816A (en) | 2001-10-22 | 2008-01-04 | Pfizer Prod Inc | 3-azabicyclo (3.1.0) hexane derivatives as opioid receptor antagonists. |
| US7381721B2 (en) | 2003-03-17 | 2008-06-03 | Adolor Corporation | Substituted piperidine compounds |
| MXPA05011070A (es) | 2003-04-14 | 2005-12-12 | Pfizer Prod Inc | Derivados de 3-azabiciclo [3.2.1] octano. |
| US7056930B2 (en) * | 2003-04-14 | 2006-06-06 | Pfizer Inc. | 2-Azabicyclo[3.3.1]nonane derivatives |
| US20040204453A1 (en) | 2003-04-14 | 2004-10-14 | Pfizer Inc | 4-Phenyl-piperidine compounds and their use as modulators of opioid receptors |
| JP2006523673A (ja) | 2003-04-15 | 2006-10-19 | ファイザー・プロダクツ・インク | オピオイド受容体活性を有する3−ベンズヒドリリデン−8−アザ−ビシクロ[3.2.1]オクタン誘導体 |
| US6992090B2 (en) | 2003-06-16 | 2006-01-31 | Adolor Corporation | Substituted piperidine compounds and methods of their use |
| EP1737853A1 (en) | 2004-02-03 | 2007-01-03 | Janssen Pharmaceutica N.V. | 3-(diheteroarylmethylene)-8-azabicyclo¬3.2.1|octane and 3-((aryl)(heteroaryl)methylene)-8-azabicyclo¬3.2.1|octane derivatives |
| US7087749B2 (en) | 2004-03-11 | 2006-08-08 | Adolor Corporation | Substituted piperidine compounds and methods of their use |
| US7538110B2 (en) | 2005-10-27 | 2009-05-26 | Adolor Corporation | Opioid antagonists |
| MY145633A (en) * | 2006-03-01 | 2012-03-15 | Theravance Inc | 8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
| CN101534827A (zh) | 2006-11-07 | 2009-09-16 | 尼克塔治疗亚拉巴马公司 | 阿片样物质激动剂和阿片样物质拮抗剂的剂型和联合给药 |
| TWI409067B (zh) | 2007-02-28 | 2013-09-21 | Theravance Inc | 8-氮雜雙環〔3.2.1〕辛烷化合物之結晶型 |
| TWI415850B (zh) | 2007-07-20 | 2013-11-21 | Theravance Inc | 製備mu類鴉片受體拮抗劑之中間物的方法 |
| EP2185553B1 (en) | 2007-08-27 | 2012-06-27 | Theravance, Inc. | Amidoalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
| TWI423801B (zh) | 2007-08-27 | 2014-01-21 | Theravance Inc | 作為μ類鴉片受體拮抗劑之8-氮雜雙環〔3.2.1〕辛基-2-羥基苯甲醯胺化合物 |
| DE602008005771D1 (de) | 2007-08-27 | 2011-05-05 | Theravance Inc | Disubstituierte alkyl-8-azabicycloä3.2.1üoktan-verbindungen als mu-opioid-rezeptorantagonisten |
| WO2009029253A1 (en) | 2007-08-27 | 2009-03-05 | Theravance, Inc. | Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
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2007
- 2007-02-07 MY MYPI20070176A patent/MY145633A/en unknown
- 2007-02-26 TW TW096106339A patent/TWI379832B/zh active
- 2007-02-28 PT PT07752111T patent/PT2001876E/pt unknown
- 2007-02-28 RU RU2008138875/04A patent/RU2423362C2/ru active
- 2007-02-28 SI SI200730691T patent/SI2001876T1/sl unknown
- 2007-02-28 PL PL07752111T patent/PL2001876T3/pl unknown
- 2007-02-28 AR ARP070100835A patent/AR059690A1/es active IP Right Grant
- 2007-02-28 EP EP07752111A patent/EP2001876B1/en active Active
- 2007-02-28 CA CA2646409A patent/CA2646409C/en active Active
- 2007-02-28 MX MX2008011165A patent/MX2008011165A/es active IP Right Grant
- 2007-02-28 DK DK07752111.0T patent/DK2001876T3/da active
- 2007-02-28 NZ NZ570764A patent/NZ570764A/en not_active IP Right Cessation
- 2007-02-28 AU AU2007224213A patent/AU2007224213B2/en active Active
- 2007-02-28 US US11/711,961 patent/US7622508B2/en active Active
- 2007-02-28 WO PCT/US2007/005388 patent/WO2007103187A2/en not_active Ceased
- 2007-02-28 PE PE2007000212A patent/PE20071311A1/es active IP Right Grant
- 2007-02-28 BR BRPI0708490A patent/BRPI0708490B8/pt not_active IP Right Cessation
- 2007-02-28 HR HR20110590T patent/HRP20110590T1/hr unknown
- 2007-02-28 JP JP2008557405A patent/JP5086280B2/ja active Active
- 2007-02-28 AT AT07752111T patent/ATE509928T1/de active
- 2007-02-28 KR KR1020087024027A patent/KR101376479B1/ko active Active
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2008
- 2008-08-26 IL IL193690A patent/IL193690A/en active IP Right Grant
- 2008-09-17 MA MA31246A patent/MA30284B1/fr unknown
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2009
- 2009-10-14 US US12/578,715 patent/US8263618B2/en active Active
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2011
- 2011-08-09 CY CY20111100762T patent/CY1111747T1/el unknown
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2012
- 2012-06-20 US US13/527,942 patent/US8664242B2/en active Active
- 2012-08-01 JP JP2012171119A patent/JP2012211193A/ja not_active Withdrawn
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2014
- 2014-01-15 US US14/156,014 patent/US8927573B2/en active Active
- 2014-11-06 US US14/534,798 patent/US9206172B2/en active Active
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2015
- 2015-10-29 US US14/926,225 patent/US9663509B2/en active Active
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2017
- 2017-04-25 US US15/496,269 patent/US10081626B2/en active Active
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2018
- 2018-08-16 US US15/998,823 patent/US10377751B2/en active Active
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2019
- 2019-06-24 US US16/449,857 patent/US10745394B2/en active Active
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2020
- 2020-07-07 US US16/922,414 patent/US11548887B2/en active Active
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2022
- 2022-12-09 US US18/078,891 patent/US20230183232A1/en not_active Abandoned
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