AR080733A1 - Aril-ciclohexil-tetraazabenzo[e]azulenos, un proceso para su obtencion, una composicion farmaceutica que los contiene y su uso para la preparacion de un medicamento para el tratamiento de enfermedades mediadas por el antagonismo del receptor de v1a - Google Patents
Aril-ciclohexil-tetraazabenzo[e]azulenos, un proceso para su obtencion, una composicion farmaceutica que los contiene y su uso para la preparacion de un medicamento para el tratamiento de enfermedades mediadas por el antagonismo del receptor de v1aInfo
- Publication number
- AR080733A1 AR080733A1 ARP110101019A ARP110101019A AR080733A1 AR 080733 A1 AR080733 A1 AR 080733A1 AR P110101019 A ARP110101019 A AR P110101019A AR P110101019 A ARP110101019 A AR P110101019A AR 080733 A1 AR080733 A1 AR 080733A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- halogen
- alkoxy
- group
- cyano
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 230000008485 antagonism Effects 0.000 title 1
- 201000010099 disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- 230000001404 mediated effect Effects 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 abstract 9
- 150000002367 halogens Chemical class 0.000 abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 6
- 125000001424 substituent group Chemical group 0.000 abstract 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 206010001488 Aggression Diseases 0.000 abstract 1
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 206010007558 Cardiac failure chronic Diseases 0.000 abstract 1
- 208000020401 Depressive disease Diseases 0.000 abstract 1
- 208000005171 Dysmenorrhea Diseases 0.000 abstract 1
- 206010013935 Dysmenorrhoea Diseases 0.000 abstract 1
- 206010057671 Female sexual dysfunction Diseases 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 206010053198 Inappropriate antidiuretic hormone secretion Diseases 0.000 abstract 1
- 206010057672 Male sexual dysfunction Diseases 0.000 abstract 1
- 206010029164 Nephrotic syndrome Diseases 0.000 abstract 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 abstract 1
- 230000016571 aggressive behavior Effects 0.000 abstract 1
- 208000012761 aggressive behavior Diseases 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000005557 antagonist Substances 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 208000029560 autism spectrum disease Diseases 0.000 abstract 1
- 208000019425 cirrhosis of liver Diseases 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000001575 pathological effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 201000000980 schizophrenia Diseases 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Pregnancy & Childbirth (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Estos compuestos actuan, como moduladores del receptor de V1a y en particular como antagonistas del receptor de V1a. Se reivindica además su obtencion, composiciones farmacéuticas que los contienen y su utilizacion como medicamentos. Los compuestos activos que se proveen en la presente solicitud son utiles como sustancias terapéuticas que actuan a nivel periférico y central en estados patologicos tales como la dismenorrea, disfuncion sexual masculina o femenina, hipertension, fallo cardíaco cronico, secrecion inapropiada de vasopresina, cirrosis hepática, síndrome nefrotico, ansiedad, trastornos depresivos, trastorno obsesivo-compulsivo, trastornos del espectro autista, esquizofrenia y conducta agresiva. Reivindicacion 1: Un compuesto de la formula (1) en la que R1 se elige entre el grupo formado por H, alquilo C1-6, sin sustituir o sustituido de 1 a 5 veces por sustituyentes elegidos individualmente entre el grupo formado por OH, halogeno, ciano y alcoxi C1-6, -(CH2)p-R4, p es el numero 0 o 1, R4 = fenilo o heteroarilo de 5 o 6 eslabones, cada uno de ellos está sin sustituir o sustituido de 1 a 5 veces por sustituyentes elegidos individualmente entre el grupo formado por OH, halogeno, ciano, alcoxi C1-6, halogeno-alquilo C1-6, halogeno-alcoxi C1-6 e hidroxi-alquilo C1-6, -S(O)2-alquilo C1-6, dicho alquilo C1-6 está sin sustituir o sustituido de 1 a 5 veces por sustituyentes elegidos individualmente entre el grupo formado por OH, halogeno, ciano y alcoxi C1-6, -C(O)-alquilo C1-6, dicho alquilo C1-6 está sin sustituir o sustituido de 1 a 5 veces por sustituyentes elegidos individualmente entre el grupo formado por OH, halogeno, ciano y alcoxi C1-6, y -C(O)O-alquilo C1-6, dicho alquilo C1-6 está sin sustituir o sustituido de 1 a 5 veces por sustituyentes elegidos individualmente entre el grupo formado por OH, halogeno, ciano y alcoxi C1-6; R2 se elige entre el grupo formado por hidrogeno y halogeno; R3 es arilo, sin sustituir o sustituido de 1 a 5 veces por sustituyentes elegidos individualmente entre el grupo formado por OH, halogeno, ciano, alquilo C1-6, alcoxi C1-6, halogeno- alquilo C1-6, halogeno-alcoxi C1-6 e hidroxi-alquilo C1-6 o una sal farmacéuticamente aceptable de los mismos.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10158871 | 2010-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR080733A1 true AR080733A1 (es) | 2012-05-02 |
Family
ID=43858425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110101019A AR080733A1 (es) | 2010-03-31 | 2011-03-29 | Aril-ciclohexil-tetraazabenzo[e]azulenos, un proceso para su obtencion, una composicion farmaceutica que los contiene y su uso para la preparacion de un medicamento para el tratamiento de enfermedades mediadas por el antagonismo del receptor de v1a |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8420633B2 (es) |
| EP (1) | EP2552919B1 (es) |
| JP (1) | JP5599936B2 (es) |
| KR (1) | KR101488073B1 (es) |
| CN (1) | CN102822176B (es) |
| AR (1) | AR080733A1 (es) |
| BR (1) | BR112012024306A2 (es) |
| CA (1) | CA2786657A1 (es) |
| ES (1) | ES2523570T3 (es) |
| MX (1) | MX2012009941A (es) |
| RU (1) | RU2566759C2 (es) |
| TW (1) | TWI409264B (es) |
| WO (1) | WO2011120877A1 (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009315754B2 (en) * | 2008-11-13 | 2013-08-15 | F. Hoffmann-La Roche Ag | Spiro-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulenes |
| PE20110590A1 (es) * | 2008-11-18 | 2011-08-31 | Hoffmann La Roche | Alquilciclohexileteres de dihidrotetraazabenzoazulenos |
| BRPI0922303B1 (pt) | 2008-11-28 | 2019-11-12 | Hoffmann La Roche | arilciclo-hexiléteres de di-hidrotetra-azabenzoazulenos, seu processo de preparação, composição farmacêutica que os compreende e uso |
| US8420633B2 (en) | 2010-03-31 | 2013-04-16 | Hoffmann-La Roche Inc. | Aryl-cyclohexyl-tetraazabenzo[e]azulenes |
| US8461151B2 (en) * | 2010-04-13 | 2013-06-11 | Hoffmann-La Roche Inc. | Aryl-/heteroaryl-cyclohexenyl-tetraazabenzo[e]azulenes |
| US8492376B2 (en) | 2010-04-21 | 2013-07-23 | Hoffmann-La Roche Inc. | Heteroaryl-cyclohexyl-tetraazabenzo[e]azulenes |
| US8481528B2 (en) | 2010-04-26 | 2013-07-09 | Hoffmann-La Roche Inc. | Heterobiaryl-cyclohexyl-tetraazabenzo[e]azulenes |
| US8513238B2 (en) | 2010-05-10 | 2013-08-20 | Hoffmann-La Roche Inc. | Heteroaryl-cyclohexyl-tetraazabenzo[E]azulenes |
| CN104628555B (zh) * | 2015-01-05 | 2016-11-30 | 烟台蓓丰医药科技有限公司 | 一种药物中间体4-(4-氯苯基)环己基-1-甲酸的合成方法 |
| JP6657611B2 (ja) * | 2015-06-15 | 2020-03-04 | Dic株式会社 | カルボニル化合物の製造方法 |
| WO2017191117A1 (en) | 2016-05-03 | 2017-11-09 | Bayer Pharma Aktiengesellschaft | V1a receptor antagonists for use in the treatment of renal diseases |
| TW202241905A (zh) | 2020-12-18 | 2022-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的氮化合物 |
| KR20230122094A (ko) | 2020-12-18 | 2023-08-22 | 메르크 파텐트 게엠베하 | Oled에 사용하기 위한 청색 형광 방출체로서의 인돌로[3.2.1-jk]카르바졸-6-카르보니트릴유도체 |
| JP2025507608A (ja) | 2022-02-23 | 2025-03-21 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機エレクトロルミネセント素子用の芳香族複素環 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5516774A (en) * | 1993-07-29 | 1996-05-14 | American Cyanamid Company | Tricyclic diazepine vasopressin antagonists and oxytocin antagonists |
| US5521173A (en) | 1995-01-17 | 1996-05-28 | American Home Products Corporation | Tricyclic benzazepine vasopressin antagonists |
| IL133788A0 (en) * | 1997-07-30 | 2001-04-30 | American Home Prod | Tricyclic vasopressin agonists |
| TR200102069T2 (tr) | 1999-01-19 | 2001-11-21 | Ortho-Mcneil Pharmaceutical, Inc. | Vasopresin reseptörü antagonistleri olarak trisiklik benzodiazepinler. |
| US7109193B2 (en) * | 2001-04-12 | 2006-09-19 | Wyeth | Tricyclic diazepines tocolytic oxytocin receptor antagonists |
| US7022699B2 (en) | 2001-04-12 | 2006-04-04 | Wyeth | Cyclohexenyl phenyl diazepines vasopressin and oxytocin receptor modulators |
| GB0303852D0 (en) * | 2003-02-19 | 2003-03-26 | Pfizer Ltd | Triazole compounds useful in therapy |
| AP2005003376A0 (en) * | 2003-02-19 | 2005-09-30 | Pfizer | Triazole compounds useful in therapy. |
| GB0400700D0 (en) * | 2004-01-13 | 2004-02-18 | Pfizer Ltd | Compounds useful in therapy |
| GEP20094723B (en) | 2004-05-25 | 2009-07-10 | Pfizer Prod Inc | Tetraazabenzo [e] azulene derivatives and analogs thereof |
| KR100840852B1 (ko) | 2004-05-25 | 2008-06-23 | 화이자 프로덕츠 인크. | 테트라아자벤조[ｅ]아줄렌 유도체 및 이의 유사체 |
| GB0412874D0 (en) * | 2004-06-09 | 2004-07-14 | Pfizer Ltd | Novel pharmaceuticals |
| EP1632494A1 (en) | 2004-08-24 | 2006-03-08 | Ferring B.V. | Vasopressin v1a antagonists |
| BRPI0514458A (pt) * | 2004-08-25 | 2008-06-10 | Pfizer | triazolbenzodiazepinas e seu uso como antagonistas de vasopressina |
| JP2008539220A (ja) | 2005-04-26 | 2008-11-13 | ファイザー・リミテッド | バソプレシンアンタゴニストとしてのトリアゾール誘導体 |
| EP1885713A1 (en) | 2005-05-18 | 2008-02-13 | Pfizer Limited | 1, 2, 4 -triazole derivatives as vasopressin antagonists |
| WO2008084005A1 (en) | 2007-01-12 | 2008-07-17 | F. Hoffmann-La Roche Ag | Spiropiperidine glycinamide derivatives |
| PE20110590A1 (es) | 2008-11-18 | 2011-08-31 | Hoffmann La Roche | Alquilciclohexileteres de dihidrotetraazabenzoazulenos |
| US8420633B2 (en) | 2010-03-31 | 2013-04-16 | Hoffmann-La Roche Inc. | Aryl-cyclohexyl-tetraazabenzo[e]azulenes |
| US8461151B2 (en) | 2010-04-13 | 2013-06-11 | Hoffmann-La Roche Inc. | Aryl-/heteroaryl-cyclohexenyl-tetraazabenzo[e]azulenes |
| US8492376B2 (en) | 2010-04-21 | 2013-07-23 | Hoffmann-La Roche Inc. | Heteroaryl-cyclohexyl-tetraazabenzo[e]azulenes |
| US8481528B2 (en) | 2010-04-26 | 2013-07-09 | Hoffmann-La Roche Inc. | Heterobiaryl-cyclohexyl-tetraazabenzo[e]azulenes |
| US8513238B2 (en) | 2010-05-10 | 2013-08-20 | Hoffmann-La Roche Inc. | Heteroaryl-cyclohexyl-tetraazabenzo[E]azulenes |
-
2011
- 2011-03-24 US US13/070,519 patent/US8420633B2/en not_active Expired - Fee Related
- 2011-03-25 EP EP11711074.2A patent/EP2552919B1/en not_active Not-in-force
- 2011-03-25 ES ES11711074.2T patent/ES2523570T3/es active Active
- 2011-03-25 JP JP2013501767A patent/JP5599936B2/ja not_active Expired - Fee Related
- 2011-03-25 WO PCT/EP2011/054582 patent/WO2011120877A1/en not_active Ceased
- 2011-03-25 MX MX2012009941A patent/MX2012009941A/es active IP Right Grant
- 2011-03-25 CA CA2786657A patent/CA2786657A1/en not_active Abandoned
- 2011-03-25 CN CN201180015556.2A patent/CN102822176B/zh not_active Expired - Fee Related
- 2011-03-25 BR BR112012024306A patent/BR112012024306A2/pt not_active IP Right Cessation
- 2011-03-25 RU RU2012144576/04A patent/RU2566759C2/ru not_active IP Right Cessation
- 2011-03-25 KR KR1020127028482A patent/KR101488073B1/ko not_active Expired - Fee Related
- 2011-03-29 AR ARP110101019A patent/AR080733A1/es unknown
- 2011-03-30 TW TW100111093A patent/TWI409264B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HK1174613A1 (en) | 2013-06-14 |
| US20110245237A1 (en) | 2011-10-06 |
| RU2012144576A (ru) | 2014-05-10 |
| JP5599936B2 (ja) | 2014-10-01 |
| TWI409264B (zh) | 2013-09-21 |
| ES2523570T3 (es) | 2014-11-27 |
| EP2552919A1 (en) | 2013-02-06 |
| CN102822176B (zh) | 2015-07-22 |
| CA2786657A1 (en) | 2011-10-06 |
| US8420633B2 (en) | 2013-04-16 |
| RU2566759C2 (ru) | 2015-10-27 |
| BR112012024306A2 (pt) | 2016-05-24 |
| KR101488073B1 (ko) | 2015-01-29 |
| TW201202243A (en) | 2012-01-16 |
| MX2012009941A (es) | 2012-09-21 |
| CN102822176A (zh) | 2012-12-12 |
| JP2013523675A (ja) | 2013-06-17 |
| WO2011120877A1 (en) | 2011-10-06 |
| EP2552919B1 (en) | 2014-09-24 |
| KR20130023228A (ko) | 2013-03-07 |
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