CA2783468C - Ppar-sparing thiazolidinedione salts for the treatment of metabolic diseases - Google Patents
Ppar-sparing thiazolidinedione salts for the treatment of metabolic diseases Download PDFInfo
- Publication number
- CA2783468C CA2783468C CA2783468A CA2783468A CA2783468C CA 2783468 C CA2783468 C CA 2783468C CA 2783468 A CA2783468 A CA 2783468A CA 2783468 A CA2783468 A CA 2783468A CA 2783468 C CA2783468 C CA 2783468C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- alkyl
- aliphatic
- mmol
- formula
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or 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
- C07D277/34—Oxygen atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- 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
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28676509P | 2009-12-15 | 2009-12-15 | |
| US61/286,765 | 2009-12-15 | ||
| PCT/US2010/060439 WO2011084453A1 (en) | 2009-12-15 | 2010-12-15 | Ppar-sparing thiazolidinedione salts for the treatment of metabolic diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2783468A1 CA2783468A1 (en) | 2011-07-14 |
| CA2783468C true CA2783468C (en) | 2018-10-09 |
Family
ID=43501294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2783468A Active CA2783468C (en) | 2009-12-15 | 2010-12-15 | Ppar-sparing thiazolidinedione salts for the treatment of metabolic diseases |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8912335B2 (enExample) |
| EP (1) | EP2513070B1 (enExample) |
| JP (1) | JP5634526B2 (enExample) |
| KR (3) | KR20120107493A (enExample) |
| CN (1) | CN102753539B (enExample) |
| AU (1) | AU2010340055B2 (enExample) |
| CA (1) | CA2783468C (enExample) |
| DK (1) | DK2513070T3 (enExample) |
| ES (1) | ES2658168T3 (enExample) |
| HU (1) | HUE038042T2 (enExample) |
| MX (1) | MX2012006725A (enExample) |
| NO (1) | NO2513070T3 (enExample) |
| NZ (1) | NZ600390A (enExample) |
| PL (1) | PL2513070T3 (enExample) |
| RU (1) | RU2564661C2 (enExample) |
| WO (1) | WO2011084453A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120107493A (ko) | 2009-12-15 | 2012-10-02 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 대사성 질환의 치료를 위한 ppar 절약형 티아졸리딘디온염 |
| UA116217C2 (uk) | 2012-10-09 | 2018-02-26 | Санофі | Пептидна сполука як подвійний агоніст рецепторів glp1-1 та глюкагону |
| AU2013366692B2 (en) | 2012-12-21 | 2017-11-23 | Sanofi | Dual GLP1/GIP or trigonal GLP1/GIP/Glucagon agonists |
| US9562012B2 (en) * | 2013-07-22 | 2017-02-07 | Metabolic Solutions Development Company, Llc | PPAR-sparing compounds for the treatment of metabolic diseases |
| EP3080154B1 (en) | 2013-12-13 | 2018-02-07 | Sanofi | Dual glp-1/gip receptor agonists |
| EP3080152A1 (en) | 2013-12-13 | 2016-10-19 | Sanofi | Non-acylated exendin-4 peptide analogues |
| WO2015086733A1 (en) | 2013-12-13 | 2015-06-18 | Sanofi | Dual glp-1/glucagon receptor agonists |
| WO2015086728A1 (en) | 2013-12-13 | 2015-06-18 | Sanofi | Exendin-4 peptide analogues as dual glp-1/gip receptor agonists |
| TW201625670A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自exendin-4之雙重glp-1/升糖素受體促效劑 |
| TW201625668A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 作為胜肽性雙重glp-1/昇糖素受體激動劑之艾塞那肽-4衍生物 |
| TW201625669A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自艾塞那肽-4(Exendin-4)之肽類雙重GLP-1/升糖素受體促效劑 |
| US9932381B2 (en) | 2014-06-18 | 2018-04-03 | Sanofi | Exendin-4 derivatives as selective glucagon receptor agonists |
| AR105319A1 (es) | 2015-06-05 | 2017-09-27 | Sanofi Sa | Profármacos que comprenden un conjugado agonista dual de glp-1 / glucagón conector ácido hialurónico |
| TW201706291A (zh) | 2015-07-10 | 2017-02-16 | 賽諾菲公司 | 作為選擇性肽雙重glp-1/升糖素受體促效劑之新毒蜥外泌肽(exendin-4)衍生物 |
| US20210038566A1 (en) | 2018-02-08 | 2021-02-11 | Enyo Pharma | Use of modulators of neet proteins for the treatment of infection |
| CN111689934B (zh) * | 2020-06-24 | 2022-08-02 | 郑州大学 | 14-脱羟-13-脱氢穿心莲内酯-12-磺酸钾的单晶体及制备方法 |
| GB202210503D0 (en) | 2022-07-18 | 2022-08-31 | Univ Court Univ Of Glasgow | Materials and methods for treatment of chronic myeloid leukemia (CML) |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5522636A (en) | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
| US4582839A (en) | 1984-03-21 | 1986-04-15 | Takeda Chemical Industries, Ltd. | 2,4-thiazolidinediones |
| WO1985004170A1 (fr) | 1984-03-21 | 1985-09-26 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, leur procede de preparation et compositions medicinales les contenant |
| WO1986002073A1 (fr) | 1984-10-03 | 1986-04-10 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant |
| CN1003445B (zh) | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物,其制备方法和用途 |
| AR240698A1 (es) | 1985-01-19 | 1990-09-28 | Takeda Chemical Industries Ltd | Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales |
| US5167228A (en) | 1987-06-26 | 1992-12-01 | Brigham And Women's Hospital | Assessment and modification of endogenous circadian phase and amplitude |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5143930A (en) | 1990-02-07 | 1992-09-01 | Sankyo Company, Limited | Thiazolidine derivatives with anti-diabetic activity, their preparation and their use |
| US5356913A (en) | 1990-02-09 | 1994-10-18 | The Upjohn Company | Use of insulin sensitizing agents to treat hypertension |
| US5441971A (en) | 1991-04-11 | 1995-08-15 | The Upjohn Company | Thiazolidinedione derivatives, production and use thereof |
| DE69231886T2 (de) | 1991-04-11 | 2002-03-28 | Pharmacia & Upjohn Co., Kalamazoo | Thiazolidindionderivate, herstellung und anwendung |
| NO302471B1 (no) | 1991-12-26 | 1998-03-09 | Sankyo Co | Tiazolidinforbindelser og farmasöytisk preparat |
| US5886026A (en) | 1993-07-19 | 1999-03-23 | Angiotech Pharmaceuticals Inc. | Anti-angiogenic compositions and methods of use |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| TWI238064B (en) * | 1995-06-20 | 2005-08-21 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
| IL118778A (en) | 1995-07-03 | 1999-07-14 | Sankyo Co | Pharmaceutical compositions for the treatment of arteriosclerosis and xanthoma containing an hmg-coa reductase inhibitor |
| US7407978B2 (en) | 1999-04-06 | 2008-08-05 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
| EP1210087A2 (en) | 1999-04-29 | 2002-06-05 | City of Hope | Pentoxifylline, pioglitazone and metformin are inhibitors of formation of advanced glycation endproducts (age's) |
| US6331596B1 (en) | 1999-06-28 | 2001-12-18 | Basf Corporation | Method of preparing carbamate-functional polymers |
| MXPA01013199A (es) | 1999-06-30 | 2003-08-20 | Tularik Inc | Compuestos para la modulacion de la actividad de ppary. |
| AU6118001A (en) | 2000-05-03 | 2001-11-12 | Tularik Inc | Combination therapeutic compositions and methods of use |
| AU2002226365A1 (en) | 2000-12-01 | 2002-06-11 | Novartis Ag | Combinations of an angiotensin receptor antagonist and an anti-hypertensive drug or a statin, for the treatment of sexual dysfunction |
| US7009057B2 (en) | 2001-04-26 | 2006-03-07 | Zentiva A.S. | Method for obtaining pioglitazone as an antidiabetic agent |
| US7135485B2 (en) | 2001-09-28 | 2006-11-14 | Teva Pharmaceutical Industries Ltd. | Pioglitazone hydrochloride |
| AUPS236902A0 (en) | 2002-05-16 | 2002-06-13 | Northern Sydney Area Health Service | Composition and method for treating hypertension |
| WO2004007490A2 (en) | 2002-07-16 | 2004-01-22 | Cadila Healthcare Limited | A process to prepare pioglitazone via several intermediates. |
| US20060083784A1 (en) | 2002-08-07 | 2006-04-20 | Smithkline Beecham Corporation | Amorphous pharmaceutical compositions |
| US7230016B2 (en) | 2003-05-13 | 2007-06-12 | Synthon Ip Inc. | Pioglitazone salts, such as pioglitazone sulfate, and pharmaceutical compositions and processes using the same |
| US20070078170A1 (en) | 2003-08-28 | 2007-04-05 | Khanduri Chandra H | Process for the preparation of pioglitazone |
| AR047541A1 (es) | 2004-02-13 | 2006-01-25 | Sandoz Ag | Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas |
| JP4475983B2 (ja) | 2004-03-03 | 2010-06-09 | 学校法人日本大学 | Bmal1を阻害する方法 |
| AU2005288080B2 (en) | 2004-09-28 | 2011-10-13 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compound |
| PL2001468T3 (pl) * | 2006-03-16 | 2013-03-29 | Metabolic Solutions Dev Co Llc | Analogi tiazolidynodionu |
| JP2009530293A (ja) | 2006-03-16 | 2009-08-27 | メタボリック ソリューションズ ディベロップメント カンパニー | チアゾリジンジオン類似体およびグルココルチコイドアゴニストの併用療法 |
| NZ571870A (en) | 2006-03-16 | 2011-07-29 | Metabolic Solutions Dev Co | Thiazolidinedione analogues for the treatment of hypertension and for lowering lipids |
| US8304441B2 (en) | 2007-09-14 | 2012-11-06 | Metabolic Solutions Development Company, Llc | Thiazolidinedione analogues for the treatment of metabolic diseases |
| KR101537830B1 (ko) | 2007-09-14 | 2015-07-17 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 고혈압 치료용 티아졸리딘디온 유사체 |
| US8722710B2 (en) | 2007-09-26 | 2014-05-13 | Deuterx, Llc | Deuterium-enriched pioglitazone |
| NZ590774A (en) * | 2008-08-07 | 2012-09-28 | Pulmagen Therapeutics Inflammation Ltd | Substantially pure 5R enantiomers of pioglitazone and rosiglitazone for treating inflammatory respiratory diseases |
| WO2010105048A1 (en) | 2009-03-12 | 2010-09-16 | Metabolic Solutions Development Company | Thiazolidinedione analogues |
| WO2011017244A1 (en) | 2009-08-05 | 2011-02-10 | Metabolic Solutions Development Company | Polymorphs of 5-(4-(2-(5-ethylpyridin-2-yl)-2-oxoethoxy)benzyl)-1,3-thiazolidine-2,4-dione (mitoglitazone) |
| US20130053350A1 (en) | 2009-12-15 | 2013-02-28 | Metabolic Solutions Development Company, Llc | Ppar-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| KR20120107493A (ko) | 2009-12-15 | 2012-10-02 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 대사성 질환의 치료를 위한 ppar 절약형 티아졸리딘디온염 |
| CA2783262A1 (en) | 2009-12-15 | 2011-07-14 | Metabolic Solutions Development Company, Llc | Ppar-sparing thiazolidinediones and combinations for the treatment of obesity and other metabolic diseases |
| US20120322728A1 (en) | 2009-12-15 | 2012-12-20 | Metabolic Solutions Development Company, Llc | Ppar-sparing thiazolidinediones and combinations for the treatment of diabetes mellitus and other metabolic diseases |
| JP2013525362A (ja) | 2010-04-21 | 2013-06-20 | メタボリック ソリューションズ ディベロップメント カンパニー, エルエルシー | チアゾリジンジオン類似体 |
-
2010
- 2010-12-15 KR KR1020127018388A patent/KR20120107493A/ko not_active Ceased
- 2010-12-15 AU AU2010340055A patent/AU2010340055B2/en active Active
- 2010-12-15 JP JP2012544740A patent/JP5634526B2/ja active Active
- 2010-12-15 RU RU2012129930/04A patent/RU2564661C2/ru active
- 2010-12-15 WO PCT/US2010/060439 patent/WO2011084453A1/en not_active Ceased
- 2010-12-15 KR KR1020177010102A patent/KR102029560B1/ko active Active
- 2010-12-15 HU HUE10796247A patent/HUE038042T2/hu unknown
- 2010-12-15 ES ES10796247.4T patent/ES2658168T3/es active Active
- 2010-12-15 PL PL10796247T patent/PL2513070T3/pl unknown
- 2010-12-15 DK DK10796247.4T patent/DK2513070T3/en active
- 2010-12-15 US US13/515,508 patent/US8912335B2/en active Active
- 2010-12-15 NZ NZ600390A patent/NZ600390A/xx unknown
- 2010-12-15 EP EP10796247.4A patent/EP2513070B1/en active Active
- 2010-12-15 CA CA2783468A patent/CA2783468C/en active Active
- 2010-12-15 NO NO10796247A patent/NO2513070T3/no unknown
- 2010-12-15 CN CN201080063893.4A patent/CN102753539B/zh active Active
- 2010-12-15 KR KR1020187022229A patent/KR102029611B1/ko active Active
- 2010-12-15 MX MX2012006725A patent/MX2012006725A/es active IP Right Grant
-
2014
- 2014-10-30 US US14/528,163 patent/US9126959B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2513070A1 (en) | 2012-10-24 |
| RU2012129930A (ru) | 2014-01-27 |
| CA2783468A1 (en) | 2011-07-14 |
| US20150051406A1 (en) | 2015-02-19 |
| WO2011084453A1 (en) | 2011-07-14 |
| RU2564661C2 (ru) | 2015-10-10 |
| KR20120107493A (ko) | 2012-10-02 |
| AU2010340055B2 (en) | 2014-07-24 |
| KR102029611B1 (ko) | 2019-10-07 |
| DK2513070T3 (en) | 2018-01-22 |
| US20120309975A1 (en) | 2012-12-06 |
| ES2658168T3 (es) | 2018-03-08 |
| HUE038042T2 (hu) | 2018-09-28 |
| JP2013514367A (ja) | 2013-04-25 |
| HK1174330A1 (en) | 2013-06-07 |
| NO2513070T3 (enExample) | 2018-04-07 |
| KR20170044214A (ko) | 2017-04-24 |
| US8912335B2 (en) | 2014-12-16 |
| JP5634526B2 (ja) | 2014-12-03 |
| EP2513070B1 (en) | 2017-11-08 |
| CN102753539A (zh) | 2012-10-24 |
| AU2010340055A1 (en) | 2012-06-28 |
| CN102753539B (zh) | 2015-09-09 |
| PL2513070T3 (pl) | 2018-05-30 |
| MX2012006725A (es) | 2012-06-28 |
| NZ600390A (en) | 2013-08-30 |
| US9126959B2 (en) | 2015-09-08 |
| KR102029560B1 (ko) | 2019-10-07 |
| KR20180089569A (ko) | 2018-08-08 |
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Effective date: 20150806 |
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| MPN | Maintenance fee for patent paid |
Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 14TH ANNIV.) - STANDARD Year of fee payment: 14 |
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Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED Effective date: 20241125 |
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