CA2478612C - Pharmaceutical composition of a pde4 or a pde3/4 inhibitor and a histamine receptor antagonist - Google Patents
Pharmaceutical composition of a pde4 or a pde3/4 inhibitor and a histamine receptor antagonist Download PDFInfo
- Publication number
- CA2478612C CA2478612C CA2478612A CA2478612A CA2478612C CA 2478612 C CA2478612 C CA 2478612C CA 2478612 A CA2478612 A CA 2478612A CA 2478612 A CA2478612 A CA 2478612A CA 2478612 C CA2478612 C CA 2478612C
- Authority
- CA
- Canada
- Prior art keywords
- inn
- phthalazin
- piperidin
- tetrahydro
- methyl
- 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.)
- Expired - Fee Related
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 26
- 239000003112 inhibitor Substances 0.000 title abstract description 20
- 101100135868 Dictyostelium discoideum pde3 gene Proteins 0.000 title abstract description 19
- 229940122236 Histamine receptor antagonist Drugs 0.000 title abstract description 18
- 239000000739 antihistaminic agent Substances 0.000 title description 11
- 101100296719 Caenorhabditis elegans pde-4 gene Proteins 0.000 title 1
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 20
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 239000004480 active ingredient Substances 0.000 claims description 87
- 238000002360 preparation method Methods 0.000 claims description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 43
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 claims description 36
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 28
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 23
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- 239000000825 pharmaceutical preparation Substances 0.000 claims description 18
- 208000006673 asthma Diseases 0.000 claims description 15
- 206010006451 bronchitis Diseases 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 15
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- 229940127557 pharmaceutical product Drugs 0.000 claims description 14
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- 238000000034 method Methods 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 8
- 230000000172 allergic effect Effects 0.000 claims description 6
- 206010052613 Allergic bronchitis Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- 206010039094 Rhinitis perennial Diseases 0.000 claims description 5
- 208000036284 Rhinitis seasonal Diseases 0.000 claims description 5
- 201000009961 allergic asthma Diseases 0.000 claims description 5
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- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 5
- 230000001932 seasonal effect Effects 0.000 claims description 5
- IGFQNTQDVNKNHQ-UHFFFAOYSA-N 3-(cyclopropylmethoxy)-n-(3,5-dichloropyridin-4-yl)-2-(difluoromethoxy)benzamide Chemical compound C1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C(OC(F)F)=C1OCC1CC1 IGFQNTQDVNKNHQ-UHFFFAOYSA-N 0.000 claims 1
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 23
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- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 21
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- YWGDOWXRIALTES-NRFANRHFSA-N bepotastine Chemical compound C1CN(CCCC(=O)O)CCC1O[C@H](C=1N=CC=CC=1)C1=CC=C(Cl)C=C1 YWGDOWXRIALTES-NRFANRHFSA-N 0.000 description 21
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- 229960000351 terfenadine Drugs 0.000 description 21
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Classifications
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- A—HUMAN NECESSITIES
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- 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
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4425—Pyridinium derivatives, e.g. pralidoxime, pyridostigmine
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A—HUMAN NECESSITIES
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02004987 | 2002-03-06 | ||
| EP02004987.0 | 2002-03-06 | ||
| PCT/EP2003/001876 WO2003074055A1 (en) | 2002-03-06 | 2003-02-25 | Pharmaceutical composition of a pde4 or a pde3/4 inhibitor and a histamine receptor antagonist |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2478612A1 CA2478612A1 (en) | 2003-09-12 |
| CA2478612C true CA2478612C (en) | 2013-12-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2478612A Expired - Fee Related CA2478612C (en) | 2002-03-06 | 2003-02-25 | Pharmaceutical composition of a pde4 or a pde3/4 inhibitor and a histamine receptor antagonist |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US20050112069A1 (enExample) |
| EP (2) | EP1849468B1 (enExample) |
| JP (1) | JP5150034B2 (enExample) |
| KR (1) | KR20040095255A (enExample) |
| CN (1) | CN101257904A (enExample) |
| AR (1) | AR038858A1 (enExample) |
| AT (1) | ATE369134T1 (enExample) |
| AU (1) | AU2003212268B2 (enExample) |
| BR (1) | BR0308220A (enExample) |
| CA (1) | CA2478612C (enExample) |
| CO (1) | CO5611148A2 (enExample) |
| CY (2) | CY1106927T1 (enExample) |
| DE (1) | DE60315426T2 (enExample) |
| DK (2) | DK1482938T3 (enExample) |
| EA (2) | EA010886B1 (enExample) |
| ES (2) | ES2400670T3 (enExample) |
| HR (1) | HRP20040909B1 (enExample) |
| IL (1) | IL163336A (enExample) |
| IS (2) | IS2536B (enExample) |
| MX (1) | MXPA04008460A (enExample) |
| NO (1) | NO335254B1 (enExample) |
| NZ (1) | NZ535611A (enExample) |
| PL (1) | PL211574B1 (enExample) |
| PT (2) | PT1482938E (enExample) |
| RS (1) | RS51018B (enExample) |
| SG (1) | SG160197A1 (enExample) |
| SI (2) | SI1849468T1 (enExample) |
| TW (1) | TWI347845B (enExample) |
| UA (1) | UA80117C2 (enExample) |
| WO (1) | WO2003074055A1 (enExample) |
| ZA (1) | ZA200407104B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8067433B2 (en) * | 2005-11-09 | 2011-11-29 | Zalicus Inc. | Methods, compositions, and kits for the treatment of ophthalmic disorders |
| WO2008074803A2 (en) * | 2006-12-20 | 2008-06-26 | Glaxo Group Limited | 4-benzyl-l ( 2h) -phthalazinones as h1 receptor antagonists |
| US20090182035A1 (en) * | 2007-04-11 | 2009-07-16 | Alcon Research, Ltd. | Use of a combination of olopatadine and cilomilast to treat non-infectious rhinitis and allergic conjunctivitis |
| CA2682730A1 (en) * | 2007-04-11 | 2008-10-23 | Alcon Research, Ltd. | Use of an inhibitor of tnf.alpha. plus an antihistamine to treat allergic rhinitis and allergic conjunctivitis |
| WO2009067597A1 (en) * | 2007-11-21 | 2009-05-28 | Decode Genetics Ehf | 4- (or 5-) substituted catechol derivatives |
| KR20090061972A (ko) * | 2007-12-12 | 2009-06-17 | 한미약품 주식회사 | 베포타스틴 ｐ-톨루엔술폰산염의 결정형, 이의 제조방법 및이를 포함하는 약학 조성물 |
| RS55624B1 (sr) | 2011-02-07 | 2017-06-30 | Scipharm Sàrl | Nova kompozicija za lečenje cistične fibroze |
| KR102226833B1 (ko) * | 2013-06-28 | 2021-03-12 | 한미약품 주식회사 | 레보세티리진 및 몬테루카스트를 포함하는 안정성이 개선된 복합 과립 제형 |
| CN106604747A (zh) * | 2014-08-26 | 2017-04-26 | 基础应用医学研究基金会 | 用于治疗和预防伴随认知缺陷或缺损的神经障碍以及神经变性疾病的产品 |
| NZ731344A (en) | 2014-10-09 | 2018-08-31 | Guangdong Raynovent Biotech Co Ltd | Hydroxyl purine compounds and applications thereof |
| CN109956947A (zh) * | 2017-12-25 | 2019-07-02 | 江苏恒瑞医药股份有限公司 | 一种cns抑制剂的新晶型、制备方法及用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2847693A1 (de) * | 1978-11-03 | 1980-05-22 | Hoechst Ag | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen |
| AU650953B2 (en) | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
| CZ290266B6 (cs) * | 1993-07-02 | 2002-06-12 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituované benzamidy, způsob jejich výroby a farmaceutické prostředky s jejich obsahem |
| US5900421A (en) * | 1997-02-11 | 1999-05-04 | Sepracor Inc. | Methods and compositions for treating allergic asthma and dermatitis using descarboethoxyloratadine |
| US5990147A (en) * | 1997-11-07 | 1999-11-23 | Schering Corporation | H3 receptor ligands of the phenyl-alkyl-imidazoles type |
| BR9804993A (pt) * | 1998-11-10 | 2000-06-06 | Panacea Biotec Ltd | Composição antialérgica e antiinflamatória |
| US6174878B1 (en) * | 1999-08-31 | 2001-01-16 | Alcon Laboratories, Inc. | Topical use of kappa opioid agonists to treat otic pain |
| AU781137B2 (en) * | 1999-10-25 | 2005-05-05 | Altana Pharma Ag | Tetrahydrothiopy ranphthalazinone derivatives as PDE4 inhibitors |
| US7585847B2 (en) * | 2000-02-03 | 2009-09-08 | Coley Pharmaceutical Group, Inc. | Immunostimulatory nucleic acids for the treatment of asthma and allergy |
| GB0115181D0 (en) * | 2001-06-20 | 2001-08-15 | Glaxo Group Ltd | Novel use |
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2003
- 2003-02-20 TW TW092103525A patent/TWI347845B/zh not_active IP Right Cessation
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- 2003-02-25 RS YUP-780/04A patent/RS51018B/sr unknown
- 2003-02-25 CN CNA038053349A patent/CN101257904A/zh active Pending
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- 2003-02-25 ES ES07112823T patent/ES2400670T3/es not_active Expired - Lifetime
- 2003-02-25 AT AT03708130T patent/ATE369134T1/de active
- 2003-02-25 HR HR20040909 patent/HRP20040909B1/xx not_active IP Right Cessation
- 2003-02-25 PT PT03708130T patent/PT1482938E/pt unknown
- 2003-02-25 SG SG200606154-3A patent/SG160197A1/en unknown
- 2003-02-25 BR BR0308220-2A patent/BR0308220A/pt not_active Application Discontinuation
- 2003-02-25 ES ES03708130T patent/ES2291618T3/es not_active Expired - Lifetime
- 2003-02-25 NZ NZ535611A patent/NZ535611A/xx not_active IP Right Cessation
- 2003-02-25 SI SI200332245T patent/SI1849468T1/sl unknown
- 2003-02-25 US US10/506,875 patent/US20050112069A1/en not_active Abandoned
- 2003-02-25 PL PL371056A patent/PL211574B1/pl unknown
- 2003-02-25 DK DK03708130T patent/DK1482938T3/da active
- 2003-02-25 CA CA2478612A patent/CA2478612C/en not_active Expired - Fee Related
- 2003-02-25 WO PCT/EP2003/001876 patent/WO2003074055A1/en not_active Ceased
- 2003-02-25 EA EA200601592A patent/EA010886B1/ru not_active IP Right Cessation
- 2003-02-25 JP JP2003572572A patent/JP5150034B2/ja not_active Expired - Fee Related
- 2003-02-25 SI SI200330970T patent/SI1482938T1/sl unknown
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- 2003-02-25 EP EP07112823A patent/EP1849468B1/en not_active Expired - Lifetime
- 2003-02-25 EA EA200401137A patent/EA007903B1/ru not_active IP Right Cessation
- 2003-02-25 UA UA20041008055A patent/UA80117C2/uk unknown
- 2003-02-25 EP EP03708130A patent/EP1482938B1/en not_active Expired - Lifetime
- 2003-02-25 PT PT71128235T patent/PT1849468E/pt unknown
- 2003-02-25 DK DK07112823.5T patent/DK1849468T3/da active
- 2003-02-27 AR ARP030100646A patent/AR038858A1/es unknown
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2004
- 2004-08-03 IL IL163336A patent/IL163336A/en not_active IP Right Cessation
- 2004-09-03 CO CO04086713A patent/CO5611148A2/es active IP Right Grant
- 2004-09-03 IS IS7438A patent/IS2536B/is unknown
- 2004-09-06 ZA ZA200407104A patent/ZA200407104B/en unknown
- 2004-10-06 NO NO20044230A patent/NO335254B1/no not_active IP Right Cessation
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2007
- 2007-10-11 CY CY20071101307T patent/CY1106927T1/el unknown
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2008
- 2008-09-04 IS IS8760A patent/IS8760A/is unknown
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2013
- 2013-02-21 CY CY20131100163T patent/CY1113894T1/el unknown
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