JP2012500794A5 - - Google Patents
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- Publication number
- JP2012500794A5 JP2012500794A5 JP2011523975A JP2011523975A JP2012500794A5 JP 2012500794 A5 JP2012500794 A5 JP 2012500794A5 JP 2011523975 A JP2011523975 A JP 2011523975A JP 2011523975 A JP2011523975 A JP 2011523975A JP 2012500794 A5 JP2012500794 A5 JP 2012500794A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- crystalline form
- solvent
- disease
- hydrochloride
- 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.)
- Granted
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- BUKBNUJDDCTKCB-UHFFFAOYSA-N 2,2,2-trifluoro-n-[(4-fluoro-3-pyridin-4-ylphenyl)methyl]acetamide Chemical compound FC1=CC=C(CNC(=O)C(F)(F)F)C=C1C1=CC=NC=C1 BUKBNUJDDCTKCB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 11
- 239000002904 solvent Substances 0.000 claims 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010010741 Conjunctivitis Diseases 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- RSFNYNQGERWCMT-UHFFFAOYSA-N (3-bromo-4-fluorophenyl)methylazanium;chloride Chemical compound Cl.NCC1=CC=C(F)C(Br)=C1 RSFNYNQGERWCMT-UHFFFAOYSA-N 0.000 claims 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 206010028594 Myocardial fibrosis Diseases 0.000 claims 1
- 201000004404 Neurofibroma Diseases 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 208000008469 Peptic Ulcer Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 229940122598 Tryptase inhibitor Drugs 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 210000001188 articular cartilage Anatomy 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 230000007882 cirrhosis Effects 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 229930195712 glutamate Natural products 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 230000001969 hypertrophic effect Effects 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000011906 peptic ulcer disease Diseases 0.000 claims 1
- 208000028169 periodontal disease Diseases 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 230000004962 physiological condition Effects 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000002750 tryptase inhibitor Substances 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- MIWWISAVSLTWHL-UHFFFAOYSA-N CCOC(Nc(c(F)ccc1OC(F)(F)F)c1C#C[Si](C)(C)C)=O Chemical compound CCOC(Nc(c(F)ccc1OC(F)(F)F)c1C#C[Si](C)(C)C)=O MIWWISAVSLTWHL-UHFFFAOYSA-N 0.000 description 1
- LHDVRBJNTZNEOO-UHFFFAOYSA-N CCOC(Nc(c(F)ccc1OC(F)(F)F)c1I)=O Chemical compound CCOC(Nc(c(F)ccc1OC(F)(F)F)c1I)=O LHDVRBJNTZNEOO-UHFFFAOYSA-N 0.000 description 1
- SNOHTJOESIRQSC-UHFFFAOYSA-N CCOC(Nc1cc(OC(F)(F)F)ccc1F)=O Chemical compound CCOC(Nc1cc(OC(F)(F)F)ccc1F)=O SNOHTJOESIRQSC-UHFFFAOYSA-N 0.000 description 1
- MNGGHWVGVZSQJT-UHFFFAOYSA-N COCC[n](cc(C(C(F)(F)F)=O)c1c(cc2)OC(F)(F)F)c1c2F Chemical compound COCC[n](cc(C(C(F)(F)F)=O)c1c(cc2)OC(F)(F)F)c1c2F MNGGHWVGVZSQJT-UHFFFAOYSA-N 0.000 description 1
- WCJRDLYNOVMUTE-UHFFFAOYSA-N COCC[n](cc(C(N(CC1)CCC1c1cc(CN)ccc1F)=O)c1c(cc2)OC(F)(F)F)c1c2F Chemical compound COCC[n](cc(C(N(CC1)CCC1c1cc(CN)ccc1F)=O)c1c(cc2)OC(F)(F)F)c1c2F WCJRDLYNOVMUTE-UHFFFAOYSA-N 0.000 description 1
- NMOMSZQWTWCGBR-UHFFFAOYSA-N COCC[n](cc(C(N(CC1)CCC1c1cc(CNC(C(F)(F)F)=O)ccc1F)=O)c1c(cc2)OC(F)(F)F)c1c2F Chemical compound COCC[n](cc(C(N(CC1)CCC1c1cc(CNC(C(F)(F)F)=O)ccc1F)=O)c1c(cc2)OC(F)(F)F)c1c2F NMOMSZQWTWCGBR-UHFFFAOYSA-N 0.000 description 1
- WEYLKNDVRTXZFH-UHFFFAOYSA-N COCC[n](cc(C(O)=O)c1c(cc2)OC(F)(F)F)c1c2F Chemical compound COCC[n](cc(C(O)=O)c1c(cc2)OC(F)(F)F)c1c2F WEYLKNDVRTXZFH-UHFFFAOYSA-N 0.000 description 1
- QXMFZKNLDCLZSX-UHFFFAOYSA-N COCC[n](ccc1c(cc2)OC(F)(F)F)c1c2F Chemical compound COCC[n](ccc1c(cc2)OC(F)(F)F)c1c2F QXMFZKNLDCLZSX-UHFFFAOYSA-N 0.000 description 1
- KTPUBEFBWBWPFI-UHFFFAOYSA-N FC(Oc(cc1)c(cc[nH]2)c2c1F)(F)F Chemical compound FC(Oc(cc1)c(cc[nH]2)c2c1F)(F)F KTPUBEFBWBWPFI-UHFFFAOYSA-N 0.000 description 1
- SWQMUKBYCVUWEB-UHFFFAOYSA-N NCc(cc1)cc(-c2ccncc2)c1F Chemical compound NCc(cc1)cc(-c2ccncc2)c1F SWQMUKBYCVUWEB-UHFFFAOYSA-N 0.000 description 1
- UURSIBMSWHTNCC-UHFFFAOYSA-N O=C(C(F)(F)F)NCc(cc1)cc(C2CCNCC2)c1F Chemical compound O=C(C(F)(F)F)NCc(cc1)cc(C2CCNCC2)c1F UURSIBMSWHTNCC-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9101808P | 2008-08-22 | 2008-08-22 | |
| US9101108P | 2008-08-22 | 2008-08-22 | |
| US61/091,018 | 2008-08-22 | ||
| US61/091,011 | 2008-08-22 | ||
| PCT/US2009/054381 WO2010022196A2 (en) | 2008-08-22 | 2009-08-20 | [4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-[7-fluoro-1-(2-methoxy-ethyl)-4-trifluoromethoxy-1h-indol-3-yl]-methanone as an inhibitor of mast cell tryptase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012500794A JP2012500794A (ja) | 2012-01-12 |
| JP2012500794A5 true JP2012500794A5 (enExample) | 2012-09-27 |
| JP5656834B2 JP5656834B2 (ja) | 2015-01-21 |
Family
ID=41198646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011523975A Active JP5656834B2 (ja) | 2008-08-22 | 2009-08-20 | 肥満細胞トリプターゼインヒビターとしての［４−（５−アミノメチル−２−フルオロ−フェニル）−ピペリジン−１−イル］−［７−フルオロ−１−（２−メトキシ−エチル）−４−トリフルオロメトキシ−１ｈ−インドール−３−イル］−メタノン |
Country Status (36)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103508936A (zh) | 2008-08-22 | 2014-01-15 | 赛诺菲-安万特 | 用于制备吲哚苄胺化合物的中间体 |
| FR2955324A1 (fr) * | 2010-01-15 | 2011-07-22 | Sanofi Aventis | [4-(5-aminomethyl-phenyl)-piperidin-1-yl]-1h-indol-3-yl]-methanones disubstituees |
| WO2011087652A1 (en) * | 2009-12-23 | 2011-07-21 | Sanofi | Tropinone benzylamines as beta-tryptase inhibitors |
| AU2010333772B2 (en) * | 2009-12-23 | 2016-07-14 | Sanofi | Prodrugs of [4[4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-(1H-pyrrolo-pyridin-yl)-methanones and synthesis thereof |
| WO2011079102A1 (en) * | 2009-12-23 | 2011-06-30 | Sanofi | Indolyl-piperidinyl benzylamines as beta-tryptase inhibitors |
| JP2013515723A (ja) * | 2009-12-23 | 2013-05-09 | サノフイ | 炎症性腸疾患の処置 |
| JP2013520506A (ja) * | 2010-02-24 | 2013-06-06 | サノフイ | 皮膚科学的なアレルギー状態の治療 |
| EP2397074B1 (en) | 2010-06-19 | 2012-10-24 | M Stenqvist AB | A system and computer readable medium for determination of transpulmonary pressure in a patient connected to a breathing apparatus |
| US8648079B2 (en) | 2011-10-07 | 2014-02-11 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds |
| DE102020120900A1 (de) * | 2020-08-07 | 2022-02-10 | Drägerwerk AG & Co. KGaA | Vorrichtung und Verfahren zur Messung der Lungen-Compliance |
| US12102622B2 (en) | 2021-02-10 | 2024-10-01 | Iolyx Therapeutics, Inc. | Methods for ophthalmic delivery of roflumilast |
| US12263160B2 (en) | 2021-09-22 | 2025-04-01 | Iolyx Therapeutics, Inc. | Methods of treating ocular inflammatory diseases |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4921475A (en) * | 1983-08-18 | 1990-05-01 | Drug Delivery Systems Inc. | Transdermal drug patch with microtubes |
| US5087240A (en) * | 1983-08-18 | 1992-02-11 | Drug Delivery Systems Inc. | Transdermal drug patch with conductive fibers |
| US4879119A (en) * | 1984-02-21 | 1989-11-07 | Yamanouchi Pharmaceutical Co., Ltd. | Patch |
| US4925673A (en) * | 1986-08-18 | 1990-05-15 | Clinical Technologies Associates, Inc. | Delivery systems for pharmacological agents encapsulated with proteinoids |
| US5163899A (en) * | 1987-03-20 | 1992-11-17 | Drug Delivery Systems Inc. | Transdermal drug delivery system |
| US5312325A (en) * | 1987-05-28 | 1994-05-17 | Drug Delivery Systems Inc | Pulsating transdermal drug delivery system |
| GB8804164D0 (en) * | 1988-02-23 | 1988-03-23 | Tucker J M | Bandage for administering physiologically active compound |
| US5008110A (en) * | 1988-11-10 | 1991-04-16 | The Procter & Gamble Company | Storage-stable transdermal patch |
| US5088977A (en) * | 1988-12-21 | 1992-02-18 | Drug Delivery Systems Inc. | Electrical transdermal drug applicator with counteractor and method of drug delivery |
| US5013556A (en) * | 1989-10-20 | 1991-05-07 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| CA2031376A1 (en) * | 1989-12-04 | 1991-06-05 | Bahram Farhadieh | Single layer transdermal drug administration system |
| JP3507486B2 (ja) * | 1991-03-15 | 2004-03-15 | アムジエン・インコーポレーテツド | 顆粒球コロニー刺激因子の肺内投与 |
| US5352456A (en) * | 1991-10-10 | 1994-10-04 | Cygnus Therapeutic Systems | Device for administering drug transdermally which provides an initial pulse of drug |
| CA2123809A1 (en) * | 1991-12-18 | 1993-06-24 | Debra L. Wilfong | Multilayered barrier structures |
| US5451569A (en) * | 1994-04-19 | 1995-09-19 | Hong Kong University Of Science And Technology R & D Corporation Limited | Pulmonary drug delivery system |
| RU2278115C2 (ru) * | 1999-05-21 | 2006-06-20 | Сайос Инк. | ПРОИЗВОДНЫЕ ИНДОЛЬНОГО РЯДА В КАЧЕСТВЕ ИНГИБИТОРОВ p38 КИНАЗЫ |
| DZ3347A1 (fr) * | 2000-05-22 | 2001-11-29 | Aventis Pharma Inc | Dérivés d'arylméthylamine pour leur utilisation comme inhibiteurs de la tryptase |
| GB0012362D0 (en) * | 2000-05-22 | 2000-07-12 | Aventis Pharma Ltd | Chemical compounds |
| EP1571150A1 (en) * | 2004-03-02 | 2005-09-07 | Aventis Pharma Deutschland GmbH | Process for the preparation of tryptase inhibitors |
| DOP2005000039A (es) * | 2004-03-26 | 2005-10-31 | Aventis Pharma Inc | Hidrocloruro de [4-(5-aminometil-2-fluoro-fenil)- piperidin-1-il]-(4-bomo-3-metil-5-propoxi-tiofen-2-il)-metanona como un inhibidor de la triptasa de mastocitos |
| AR065859A1 (es) * | 2007-03-29 | 2009-07-08 | Sanofi Aventis | Ester de 2,5-dioxo-pirrolidin-1-ilo de acido 4-bromo-3-metil-5-propoxitiofen-2- carboxilico ,su sintesis regioespecifica y un intermedio del mismo |
| AR065858A1 (es) * | 2007-03-29 | 2009-07-08 | Sanofi Aventis | Metodo para preparar el inhibidor de triptasa [ 4-(5-aminoetil-2-fluoro-fenil)-piperidin-1-il]-(4-bromo-3-metil-5-propoxi-tiofen-2-il)-metanona. |
| CN103508936A (zh) | 2008-08-22 | 2014-01-15 | 赛诺菲-安万特 | 用于制备吲哚苄胺化合物的中间体 |
-
2009
- 2009-08-20 CN CN201310276216.6A patent/CN103508936A/zh active Pending
- 2009-08-20 PE PE2009001035A patent/PE20100235A1/es not_active Application Discontinuation
- 2009-08-20 MX MX2011001135A patent/MX2011001135A/es active IP Right Grant
- 2009-08-20 NZ NZ591234A patent/NZ591234A/en not_active IP Right Cessation
- 2009-08-20 WO PCT/US2009/054381 patent/WO2010022196A2/en not_active Ceased
- 2009-08-20 PL PL09791693T patent/PL2367812T3/pl unknown
- 2009-08-20 HR HRP20151338TT patent/HRP20151338T1/hr unknown
- 2009-08-20 PT PT97916936T patent/PT2367812E/pt unknown
- 2009-08-20 CA CA2734877A patent/CA2734877C/en active Active
- 2009-08-20 RU RU2011110745/04A patent/RU2509766C2/ru active
- 2009-08-20 DK DK09791693.6T patent/DK2367812T3/en active
- 2009-08-20 AU AU2009282884A patent/AU2009282884B8/en not_active Ceased
- 2009-08-20 HU HUE09791693A patent/HUE026331T2/en unknown
- 2009-08-20 RS RS20150840A patent/RS54413B1/sr unknown
- 2009-08-20 EP EP09791693.6A patent/EP2367812B1/en active Active
- 2009-08-20 MY MYPI20110395 patent/MY150599A/en unknown
- 2009-08-20 UA UAA201103383A patent/UA104148C2/ru unknown
- 2009-08-20 SI SI200931335T patent/SI2367812T1/sl unknown
- 2009-08-20 JP JP2011523975A patent/JP5656834B2/ja active Active
- 2009-08-20 BR BRPI0916920A patent/BRPI0916920A2/pt not_active Application Discontinuation
- 2009-08-20 KR KR1020117005841A patent/KR101630217B1/ko active Active
- 2009-08-20 ES ES09791693.6T patent/ES2556764T3/es active Active
- 2009-08-20 CN CN2009801325489A patent/CN102149705B/zh active Active
- 2009-08-21 UY UY0001032069A patent/UY32069A/es not_active Application Discontinuation
- 2009-08-21 CL CL2009001759A patent/CL2009001759A1/es unknown
- 2009-08-21 AR ARP090103234A patent/AR073117A1/es active IP Right Grant
- 2009-08-21 TW TW98128222A patent/TWI473613B/zh active
-
2011
- 2011-01-21 NI NI201100024A patent/NI201100024A/es unknown
- 2011-01-24 ZA ZA2011/00597A patent/ZA201100597B/en unknown
- 2011-02-16 CR CR20110093A patent/CR20110093A/es not_active Application Discontinuation
- 2011-02-16 US US13/028,745 patent/US8217178B2/en active Active
- 2011-02-17 IL IL211265A patent/IL211265A/en active IP Right Grant
- 2011-02-18 DO DO2011000055A patent/DOP2011000055A/es unknown
- 2011-02-21 EC EC2011010841A patent/ECSP11010841A/es unknown
- 2011-02-22 CO CO11021149A patent/CO6341624A2/es not_active Application Discontinuation
- 2011-03-14 MA MA33705A patent/MA32639B1/fr unknown
-
2012
- 2012-06-27 US US13/534,580 patent/US8497379B2/en active Active
- 2012-08-13 IL IL221434A patent/IL221434A/en active IP Right Grant
-
2015
- 2015-12-15 CY CY20151101141T patent/CY1117261T1/el unknown
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