AR072396A1 - Proceso para preparar derivados de pirimidina sustituidos - Google Patents
Proceso para preparar derivados de pirimidina sustituidosInfo
- Publication number
- AR072396A1 AR072396A1 ARP090102405A AR072396A1 AR 072396 A1 AR072396 A1 AR 072396A1 AR P090102405 A ARP090102405 A AR P090102405A AR 072396 A1 AR072396 A1 AR 072396A1
- Authority
- AR
- Argentina
- Prior art keywords
- group
- formula
- compound
- hydrogen
- alkyl
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/22—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
La presente se refiere a procesos para preparar derivados de pirimidina sustituidos, utiles como intermediarios en la síntesis de los moduladores de los receptores de histamina H4, y a intermediarios en la síntesis de los moduladores de H4. Reivindicacion 1: Un proceso para preparar un compuesto de formula (1) en donde L1 es CN; Rc se selecciona del grupo formado por H, metilo, etilo, propilo, isopropilo, -CF3, ciclopropilo, y ciclobutilo; R6 es hidrogeno; R8 se selecciona del grupo formado por hidrogeno y alquilo C1-4; Z se selecciona del grupo formado por N y CH; n es 1 o 2; R9, R10 y R11 se seleccionan cada uno de manera independiente del grupo formado por hidrogeno y alquilo C1-4; y sus sales aceptables para el uso farmacéutico; que comprende hacer reaccionar un compuesto de formula (2) en donde PG1 y PG2 son cada uno de manera independiente un grupo protector de nitrogeno, con un compuesto de formula (3), en donde LG1 es un grupo saliente, en un primer solvente orgánico; y cuando LG1 es -OH, en presencia de un sistema de agentes de acoplamiento; para obtener el correspondiente compuesto de formula (4); desproteger el compuesto de formula (4), para obtener el correspondiente compuesto de formula (5); y hacer reaccionar el compuesto de formula (5) con un compuesto de formula (6), en un segundo solvente orgánico, para obtener el correspondiente compuesto de formula (1), en donde X se selecciona del grupo formado por -N(R20)2 y -OR21; en donde cada R20 se selecciona de manera independiente del grupo formado por alquilo C1-4 alternativamente los dos grupos R20 se toman juntos con el átomo de nitrogeno al cual están unidos para formar una estructura de anillos saturados seleccionada del grupo formado por piperidinilo, pirrolidinilo y morfolinilo; y en donde R21 se selecciona del grupo formado por alquilo C1-4 y bencilo. Reivindicacion 36: Un compuesto de formula (7) en donde PG3 es un grupo protector de nitrogeno; Rc se selecciona del grupo formado por H, metilo, etilo, propilo, isopropilo, -CF3, ciclopropilo, y ciclobutilo; o una de sus sales aceptables para el uso farmacéutico. Reivindicacion 39: Un compuesto de formula (8) en donde cada R0 es hidrogeno o un grupo protector de nitrogeno; y en donde los dos grupos R0 son iguales; R8 se selecciona del grupo formado por hidrogeno y alquilo C1-4; Z se selecciona del grupo formado por N y CH; n es 1 o 2; R9, R10 y R11 se seleccionan cada uno de manera independiente del grupo formado por hidrogeno y alquilo C1-4; con la condicion de que cuando R8 es hidrogeno, R9 es hidrogeno, R10 es hidrogeno, Z es N, n es 1 y R11 es metilo, entonces R0 es un grupo protector de nitrogeno, en donde el grupo protector de nitrogeno no es -C(O)OCH3; o su sal aceptable para el uso farmacéutico.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7675208P | 2008-06-30 | 2008-06-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR072396A1 true AR072396A1 (es) | 2010-08-25 |
Family
ID=41464882
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP090102405 AR072396A1 (es) | 2008-06-30 | 2009-06-29 | Proceso para preparar derivados de pirimidina sustituidos |
Country Status (36)
Country | Link |
---|---|
US (6) | US8309720B2 (es) |
EP (5) | EP2924023A1 (es) |
JP (1) | JP5416768B2 (es) |
KR (1) | KR101675354B1 (es) |
CN (1) | CN102137672B (es) |
AR (1) | AR072396A1 (es) |
AU (1) | AU2009267156B2 (es) |
BR (1) | BRPI0913644A2 (es) |
CA (1) | CA2729733C (es) |
CO (1) | CO6341560A2 (es) |
CY (1) | CY1116134T1 (es) |
DK (1) | DK2310012T3 (es) |
EA (1) | EA019361B1 (es) |
EC (1) | ECSP11010745A (es) |
ES (1) | ES2538135T3 (es) |
HK (4) | HK1156857A1 (es) |
HR (1) | HRP20150576T1 (es) |
HU (1) | HUE024949T2 (es) |
IL (4) | IL210214A (es) |
JO (1) | JO3043B1 (es) |
ME (1) | ME02154B (es) |
MX (1) | MX2011000080A (es) |
MY (1) | MY150601A (es) |
NI (1) | NI201000232A (es) |
NZ (1) | NZ590170A (es) |
PE (1) | PE20110163A1 (es) |
PL (1) | PL2310012T3 (es) |
PT (1) | PT2310012E (es) |
RS (1) | RS53985B1 (es) |
SI (1) | SI2310012T1 (es) |
SV (1) | SV2011003788A (es) |
TW (3) | TWI498326B (es) |
UA (1) | UA106724C2 (es) |
UY (1) | UY31949A (es) |
WO (1) | WO2010002774A1 (es) |
ZA (1) | ZA201100759B (es) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101460483B (zh) | 2006-03-31 | 2013-05-08 | 詹森药业有限公司 | 作为组胺h4受体调节剂的苯并咪唑-2-基嘧啶和吡嗪 |
WO2010002774A1 (en) * | 2008-06-30 | 2010-01-07 | Janssen Pharmaceutica Nv | Process for the preparation of substituted pyrimidine derivatives |
US9371311B2 (en) | 2008-06-30 | 2016-06-21 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine derivatives |
JP5574294B2 (ja) * | 2010-11-04 | 2014-08-20 | 独立行政法人科学技術振興機構 | 光磁気記録媒体及び光磁気記録方法 |
SI2964229T1 (sl) | 2013-03-06 | 2020-02-28 | Janssen Pharmaceutica Nv | Benzoimidazol-2-il pirimidin modulatorji receptorja histamina H4 |
CN106132926B (zh) * | 2014-03-28 | 2019-05-21 | 株式会社钟化 | 三苄氧羰基精氨酸的制造方法 |
AU2017362870A1 (en) | 2016-11-03 | 2019-06-20 | Bristol-Myers Squibb Company | Substituted bicycle heterocyclic derivatives useful as ROMK channel inhibitors |
Family Cites Families (28)
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US3005852A (en) | 1959-12-22 | 1961-10-24 | Gen Aniline & Film Corp | Production of sulfoxides and sulfones |
US3931195A (en) * | 1971-03-03 | 1976-01-06 | Mead Johnson & Company | Substituted piperidines |
US4191828A (en) * | 1976-04-14 | 1980-03-04 | Richardson-Merrell Inc. | Process for preparing 2-(2,2-dicyclohexylethyl)piperidine |
US4190601A (en) * | 1978-05-31 | 1980-02-26 | Union Carbide Corporation | Production of tertiary amines by reductive alkylation |
JPS5942396A (ja) * | 1982-09-02 | 1984-03-08 | Ishihara Sangyo Kaisha Ltd | リン酸アミド誘導体およびそれらを含有する殺虫、殺ダニ、殺線虫剤 |
JPS6130576A (ja) | 1984-07-24 | 1986-02-12 | Ube Ind Ltd | 2−アミノ−5−シアノピリミジンの製法 |
US5786373A (en) * | 1992-10-14 | 1998-07-28 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
GB9422391D0 (en) | 1994-11-05 | 1995-01-04 | Solvay Interox Ltd | Oxidation of organosulphur compounds |
CA2321153A1 (en) * | 1998-02-17 | 1999-08-19 | Timothy D. Cushing | Anti-viral pyrimidine derivatives |
GB9914258D0 (en) * | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
KR20020047198A (ko) * | 1999-09-30 | 2002-06-21 | 해피 페너 ; 해리 에이치. 페너 2세 | 특정 알킬렌 디아민-치환된피라졸로[1,5-a]-1,5-피리미딘 및피라졸로[1,5-a]-1,3,5-트리아진 |
IL153662A0 (en) | 2000-07-21 | 2003-07-06 | Syngenta Participations Ag | Process for the preparation of 4,6-dimethoxy-2- (methylsulfonyl)-1,3-pyrimidine |
PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
AU2002258400A1 (en) | 2001-02-16 | 2002-08-28 | Tularik Inc. | Methods of using pyrimidine-based antiviral agents |
JP2004525150A (ja) * | 2001-03-30 | 2004-08-19 | スミスクライン ビーチャム コーポレーション | 治療用化合物としてのピラゾロピリジン類の使用 |
JP2005524609A (ja) * | 2001-12-17 | 2005-08-18 | スミスクライン ビーチャム コーポレーション | ピラゾロピリダジン誘導体 |
TWI270542B (en) | 2002-02-07 | 2007-01-11 | Sumitomo Chemical Co | Method for preparing sulfone or sulfoxide compound |
CA2508914A1 (en) * | 2002-12-04 | 2004-06-17 | Gene Logic Inc. | Modulators of melanocortin receptor |
AU2004235907B2 (en) * | 2003-05-05 | 2007-08-30 | F. Hoffmann La-Roche Ag | Fused pyrimidine derivatives with CRF activity |
US7786291B2 (en) | 2004-10-27 | 2010-08-31 | Schering Corporation | Compositions and methods for short interfering nucleic acid inhibition of Nav1.8 |
JP5118029B2 (ja) | 2005-06-14 | 2013-01-16 | タイゲン バイオテクノロジー カンパニー,リミテッド | ピリミジン化合物 |
WO2007004947A1 (en) * | 2005-07-06 | 2007-01-11 | Ge Healthcare Bio-Sciences Ab | Method of preparing a separation matrix |
TW200800201A (en) * | 2005-11-18 | 2008-01-01 | Lilly Co Eli | Pyrimidinyl benzothiophene compounds |
CN101032483B (zh) * | 2006-03-09 | 2011-05-04 | 陈德桂 | 调节雄激素受体活性的乙内酰脲衍生物及其应用 |
CN101460483B (zh) * | 2006-03-31 | 2013-05-08 | 詹森药业有限公司 | 作为组胺h4受体调节剂的苯并咪唑-2-基嘧啶和吡嗪 |
JP2009532367A (ja) * | 2006-03-31 | 2009-09-10 | 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 | ヒスタミンh4受容体のモジュレーターとしてのベンゾイミダゾール−2−イルピリジン |
WO2010002774A1 (en) | 2008-06-30 | 2010-01-07 | Janssen Pharmaceutica Nv | Process for the preparation of substituted pyrimidine derivatives |
CN102137857A (zh) * | 2008-06-30 | 2011-07-27 | 詹森药业有限公司 | 用于制备苯并咪唑-2-基嘧啶衍生物的方法 |
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2009
- 2009-06-29 WO PCT/US2009/049027 patent/WO2010002774A1/en active Application Filing
- 2009-06-29 EP EP15157453.0A patent/EP2924023A1/en not_active Withdrawn
- 2009-06-29 EP EP20140161564 patent/EP2769721A3/en not_active Withdrawn
- 2009-06-29 BR BRPI0913644A patent/BRPI0913644A2/pt not_active Application Discontinuation
- 2009-06-29 UA UAA201100983A patent/UA106724C2/uk unknown
- 2009-06-29 PL PL09774225T patent/PL2310012T3/pl unknown
- 2009-06-29 ME MEP-2015-79A patent/ME02154B/me unknown
- 2009-06-29 MX MX2011000080A patent/MX2011000080A/es active IP Right Grant
- 2009-06-29 EA EA201170113A patent/EA019361B1/ru not_active IP Right Cessation
- 2009-06-29 PT PT97742258T patent/PT2310012E/pt unknown
- 2009-06-29 KR KR1020117001991A patent/KR101675354B1/ko active IP Right Grant
- 2009-06-29 AU AU2009267156A patent/AU2009267156B2/en not_active Ceased
- 2009-06-29 PE PE2010001216A patent/PE20110163A1/es not_active Application Discontinuation
- 2009-06-29 TW TW098121755A patent/TWI498326B/zh not_active IP Right Cessation
- 2009-06-29 EP EP15157463.9A patent/EP2924025A1/en not_active Withdrawn
- 2009-06-29 EP EP20090774225 patent/EP2310012B1/en active Active
- 2009-06-29 TW TW103104509A patent/TWI481603B/zh not_active IP Right Cessation
- 2009-06-29 JP JP2011516757A patent/JP5416768B2/ja not_active Expired - Fee Related
- 2009-06-29 SI SI200931188T patent/SI2310012T1/sl unknown
- 2009-06-29 TW TW103118001A patent/TW201433568A/zh unknown
- 2009-06-29 US US12/459,229 patent/US8309720B2/en active Active
- 2009-06-29 HU HUE09774225A patent/HUE024949T2/en unknown
- 2009-06-29 MY MYPI2010006258A patent/MY150601A/en unknown
- 2009-06-29 RS RS20150287A patent/RS53985B1/en unknown
- 2009-06-29 NZ NZ590170A patent/NZ590170A/en not_active IP Right Cessation
- 2009-06-29 CA CA2729733A patent/CA2729733C/en not_active Expired - Fee Related
- 2009-06-29 JO JOP/2009/0240A patent/JO3043B1/ar active
- 2009-06-29 DK DK09774225T patent/DK2310012T3/da active
- 2009-06-29 AR ARP090102405 patent/AR072396A1/es not_active Application Discontinuation
- 2009-06-29 ES ES09774225.8T patent/ES2538135T3/es active Active
- 2009-06-29 CN CN200980134933.7A patent/CN102137672B/zh not_active Expired - Fee Related
- 2009-06-29 EP EP15157445.6A patent/EP2924035A1/en not_active Withdrawn
- 2009-06-30 UY UY31949A patent/UY31949A/es unknown
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2010
- 2010-12-23 NI NI201000232A patent/NI201000232A/es unknown
- 2010-12-23 IL IL210214A patent/IL210214A/en active IP Right Grant
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2011
- 2011-01-03 SV SV2011003788A patent/SV2011003788A/es unknown
- 2011-01-04 CO CO11000461A patent/CO6341560A2/es not_active Application Discontinuation
- 2011-01-05 EC ECSP11010745 patent/ECSP11010745A/es unknown
- 2011-01-28 ZA ZA2011/00759A patent/ZA201100759B/en unknown
- 2011-10-19 HK HK11111216.2A patent/HK1156857A1/xx not_active IP Right Cessation
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2012
- 2012-10-29 US US13/663,233 patent/US9079882B2/en not_active Expired - Fee Related
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2013
- 2013-03-15 US US13/844,227 patent/US9079883B2/en not_active Expired - Fee Related
- 2013-11-11 US US14/076,955 patent/US9079884B2/en not_active Expired - Fee Related
- 2013-11-12 US US14/078,153 patent/US9006432B2/en not_active Expired - Fee Related
- 2013-11-13 US US14/079,358 patent/US9359327B2/en not_active Expired - Fee Related
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2014
- 2014-11-09 IL IL235572A patent/IL235572A/en active IP Right Grant
- 2014-11-09 IL IL235571A patent/IL235571A/en active IP Right Grant
- 2014-11-09 IL IL235570A patent/IL235570A/en active IP Right Grant
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2015
- 2015-02-26 HK HK15101911.7A patent/HK1201441A1/xx unknown
- 2015-03-23 CY CY20151100293T patent/CY1116134T1/el unknown
- 2015-05-29 HR HRP20150576TT patent/HRP20150576T1/hr unknown
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2016
- 2016-03-03 HK HK16102449.5A patent/HK1214590A1/zh unknown
- 2016-03-23 HK HK16103405.5A patent/HK1215434A1/zh unknown
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