CZ295585B6 - Indolin-2-onové deriváty, meziprodukty pro jejich přípravu, způsob jejich přípravy, farmaceutické prostředky obsahující tyto deriváty a použití těchto derivátů - Google Patents
Indolin-2-onové deriváty, meziprodukty pro jejich přípravu, způsob jejich přípravy, farmaceutické prostředky obsahující tyto deriváty a použití těchto derivátů Download PDFInfo
- Publication number
- CZ295585B6 CZ295585B6 CZ19981267A CZ126798A CZ295585B6 CZ 295585 B6 CZ295585 B6 CZ 295585B6 CZ 19981267 A CZ19981267 A CZ 19981267A CZ 126798 A CZ126798 A CZ 126798A CZ 295585 B6 CZ295585 B6 CZ 295585B6
- Authority
- CZ
- Czechia
- Prior art keywords
- group
- indolin
- cyclohexane
- formula
- spiro
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 62
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 62
- 239000000543 intermediate Substances 0.000 title abstract description 10
- 125000004095 oxindolyl group Chemical class N1(C(CC2=CC=CC=C12)=O)* 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims abstract description 28
- 229960003726 vasopressin Drugs 0.000 claims abstract description 24
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- 229910052799 carbon Inorganic materials 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 5
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- 150000001875 compounds Chemical class 0.000 claims description 264
- -1 phenoxy, benzyloxy Chemical group 0.000 claims description 111
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 68
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 61
- 239000002904 solvent Substances 0.000 claims description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 34
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- 239000012453 solvate Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 150000004677 hydrates Chemical class 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 20
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 230000002829 reductive effect Effects 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
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- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims description 12
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- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000002947 C09CA04 - Irbesartan Substances 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical group O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 claims description 5
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- 125000005905 mesyloxy group Chemical group 0.000 claims description 5
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
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- 125000005843 halogen group Chemical group 0.000 claims description 4
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- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- GOLVMRZULJWHGT-UHFFFAOYSA-N 2-cyclohexyloxyacetic acid Chemical compound OC(=O)COC1CCCCC1 GOLVMRZULJWHGT-UHFFFAOYSA-N 0.000 claims description 3
- OYHQAXYDSYSGEI-UHFFFAOYSA-N 4-ethoxypiperidine Chemical compound CCOC1CCNCC1 OYHQAXYDSYSGEI-UHFFFAOYSA-N 0.000 claims description 3
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
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- Public Health (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
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- Neurosurgery (AREA)
- Neurology (AREA)
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- Psychiatry (AREA)
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- Heart & Thoracic Surgery (AREA)
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- Addiction (AREA)
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- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9512533A FR2740136B1 (fr) | 1995-10-24 | 1995-10-24 | Derives d'indolin-2-one, procede pour leur preparation et les compositions pharmaceutiques les contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ126798A3 CZ126798A3 (cs) | 1998-08-12 |
| CZ295585B6 true CZ295585B6 (cs) | 2005-08-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19981267A CZ295585B6 (cs) | 1995-10-24 | 1996-10-24 | Indolin-2-onové deriváty, meziprodukty pro jejich přípravu, způsob jejich přípravy, farmaceutické prostředky obsahující tyto deriváty a použití těchto derivátů |
Country Status (30)
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| JP (2) | JP3274471B2 (forum.php) |
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| AU (1) | AU715841B2 (forum.php) |
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| DK (1) | DK0873309T3 (forum.php) |
| EE (1) | EE04433B1 (forum.php) |
| ES (1) | ES2191769T3 (forum.php) |
| FR (1) | FR2740136B1 (forum.php) |
| HU (1) | HUP9900331A3 (forum.php) |
| IL (1) | IL124002A (forum.php) |
| IN (1) | IN185328B (forum.php) |
| IS (1) | IS1949B (forum.php) |
| MY (1) | MY115864A (forum.php) |
| NO (1) | NO310974B1 (forum.php) |
| NZ (1) | NZ320352A (forum.php) |
| PL (1) | PL187093B1 (forum.php) |
| RU (1) | RU2167864C2 (forum.php) |
| SK (1) | SK284546B6 (forum.php) |
| TR (1) | TR199800719T2 (forum.php) |
| TW (1) | TW474917B (forum.php) |
| UA (1) | UA59345C2 (forum.php) |
| WO (1) | WO1997015556A1 (forum.php) |
| ZA (1) | ZA968945B (forum.php) |
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| FR2757157B1 (fr) * | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2775598A1 (fr) * | 1998-03-06 | 1999-09-10 | Sanofi Sa | Compositions pharmaceutiques contenant en association un antagoniste selectif des recepteurs v1a de l'arginine-vasopressine et un antagoniste selectif des recepteur v2 de l'arginine-vasopressine |
| FR2778103A1 (fr) * | 1998-04-29 | 1999-11-05 | Sanofi Sa | Compositions pharmaceutiques contenant en association un antagoniste v1a de l'arginine-vasopressine et un antagoniste des recepteurs at1 de l'angiotensine ii |
| HUP9902374A3 (en) * | 1999-07-15 | 2002-11-28 | Sanofi Aventis | Process for producing spiro[(4-cyclohexanone)-[3h]indol-2'[1'h]-on derivatives and intermediates |
| HU225703B1 (en) * | 1999-07-15 | 2007-06-28 | Sanofi Aventis | Process for producing spiro[cis-4-(betha-hydroxy-ethyloxi)-cyclohexane-[3h]indole]-2'[1'h]-one derivatives |
| HU225150B1 (en) * | 1999-07-15 | 2006-07-28 | Sanofi Aventis | Novel process for producing 2-methoxy-4-(t-butylaminocarbonyl)-benzenesulfonyl chloride |
| HUP9902376A3 (en) | 1999-07-15 | 2002-11-28 | Sanofi Aventis | Process for producing n-(1,1-dimethyl)-4-[[s'-ethoxi-4-cis-[2-(4-morpholino)-ethoxi]-2'-oxospiro[cyclohexane-1,3'-[3h]indole]-1'(2'h)yl]-sulfonyl]-3-methoxybenzamide and its salts |
| US20030103983A1 (en) * | 2002-05-09 | 2003-06-05 | Pressler Milton Lethan | Ace inhibitor-vasopressin antagonist combinations |
| US7056910B2 (en) * | 2000-11-28 | 2006-06-06 | Astellas Pharma Inc. | 1,4,5.6-tetrahydroimidazo[4,5-d]diazepine derivatives or salts thereof |
| AU2002231098A1 (en) * | 2000-12-15 | 2002-06-24 | Emory University | Nonpeptide agonists and antagonists of vasopressin receptors |
| AU2002247127A1 (en) * | 2001-02-14 | 2002-08-28 | Duke University | Therapy for cerebral vasospasm |
| US7619082B2 (en) | 2001-07-31 | 2009-11-17 | Sanofi-Aventis | Process for the preparation of 3-spiro′cyclohexan-1,3′-′3H!indolin-2′-one! derivatives |
| US7414052B2 (en) | 2004-03-30 | 2008-08-19 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| US7517899B2 (en) | 2004-03-30 | 2009-04-14 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| CA2568640C (en) | 2004-06-04 | 2011-08-09 | Teva Pharmaceutical Industries Ltd. | Pharmaceutical composition containing irbesartan |
| FR2874921B1 (fr) * | 2004-09-09 | 2006-10-20 | Sanofi Aventis Sa | Derives de 3-spiro-indolin-2-one, leur preparation et leur application en therapeutique |
| FR2874920B1 (fr) * | 2004-09-09 | 2006-10-20 | Sanofi Aventis Sa | Derives de 3-spiro-indolin-2-one comme ligand des recepteurs de la vasopressine |
| MX2007007103A (es) * | 2004-12-13 | 2008-03-10 | Lilly Co Eli | Derivados espiro como inhibidores de lipoxigenasa. |
| JP2008526702A (ja) * | 2004-12-31 | 2008-07-24 | アボット ゲーエムベーハー ウント カンパニー カーゲー | 置換オキシインドール誘導体、該誘導体を含んでいる薬物及びそれらの使用 |
| DE102005014936A1 (de) * | 2005-03-24 | 2006-12-14 | Abbott Gmbh & Co. Kg | Substituierte Oxindol-Derivate, diese enthaltende Arzneimittel und deren Verwendung |
| MY144968A (en) | 2005-04-11 | 2011-11-30 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
| AR053710A1 (es) * | 2005-04-11 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos espiroheterociclicos y sus usos como agentes terapeuticos |
| AR056317A1 (es) * | 2005-04-20 | 2007-10-03 | Xenon Pharmaceuticals Inc | Compuestos de oxindol y composicion farmaceutica |
| US7351706B2 (en) * | 2006-01-05 | 2008-04-01 | Hoffmann-La Roche Inc. | Indol-3-yl-carbonyl-spiro-piperidine derivatives |
| US20110294842A9 (en) * | 2006-10-12 | 2011-12-01 | Xenon Pharmaceuticals Inc. | Spiro (furo [3, 2-c] pyridine-3-3' -indol) -2' (1'h)-one derivatives and related compounds for the treatment of sodium-channel mediated diseases, such as pain |
| US8466188B2 (en) | 2006-10-12 | 2013-06-18 | Xenon Pharmaceuticals Inc. | Use of spiro-oxindole compounds as therapeutic agents |
| MX2009003874A (es) * | 2006-10-12 | 2009-04-22 | Xenon Pharmaceuticals Inc | Derivados de espiro-oxindol triciclicos y sus usos como agentes terapeuticos. |
| FR2927625B1 (fr) | 2008-02-19 | 2010-03-12 | Sanofi Aventis | Nouveaux derives de 3-aminoalkyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique |
| US7723372B2 (en) * | 2008-03-19 | 2010-05-25 | Hoffman-La Roche Inc. | Spiroindolinone derivatives |
| FR2930249B1 (fr) | 2008-04-21 | 2010-05-14 | Sanofi Aventis | Nouveaux derives de 3-aminoalkyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique. |
| JP5570172B2 (ja) * | 2008-10-08 | 2014-08-13 | 持田製薬株式会社 | 喫煙による循環機能不全の予防／改善または治療剤 |
| CN105218565A (zh) | 2008-10-17 | 2016-01-06 | 泽农医药公司 | 螺羟吲哚化合物及其作为治疗剂的用途 |
| WO2010045197A1 (en) * | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals, Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
| AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
| WO2011047173A2 (en) * | 2009-10-14 | 2011-04-21 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions for oral administration |
| MY165579A (en) | 2009-10-14 | 2018-04-05 | Xenon Pharmaceuticals Inc | Synthetic methods for spiro-oxindole compounds |
| US8088815B2 (en) | 2009-12-02 | 2012-01-03 | Hoffman-La Roche Inc. | Spiroindolinone pyrrolidines |
| US8288431B2 (en) | 2010-02-17 | 2012-10-16 | Hoffmann-La Roche Inc. | Substituted spiroindolinones |
| PE20121699A1 (es) | 2010-02-26 | 2012-12-22 | Xenon Pharmaceuticals Inc | Composiciones farmaceuticas del compuesto espiro-oxindol para administracion topica |
| US8217044B2 (en) | 2010-04-28 | 2012-07-10 | Hoffmann-La Roche Inc. | Spiroindolinone pyrrolidines |
| MD4202C1 (ro) * | 2012-03-21 | 2013-09-30 | Институт Химии Академии Наук Молдовы | Procedeu de obţinere a derivaţilor carbometoxi ai spiro[ciclopropan-oxindolilor] |
| MD4201C1 (ro) * | 2012-03-21 | 2013-09-30 | Институт Химии Академии Наук Молдовы | Procedeu de obţinere a derivaţilor carbonitrilici ai spiro[ciclopropan-oxindolilor] |
| BR112015021393A2 (pt) * | 2013-03-08 | 2017-07-18 | Wockhardt Ltd | processo para a preparação de (2s,5r)-7-oxo-6-sulfoóxi-2-[(((3r)-piperidina-3-carbonil)-hidrazina carbonil]-1,6-diaza-biciclo[3.2.1]- octano |
| AR103636A1 (es) | 2015-02-05 | 2017-05-24 | Teva Pharmaceuticals Int Gmbh | Métodos de tratamiento de neuralgia postherpética con una formulación tópica de un compuesto de espiro-oxindol |
| HU231206B1 (hu) | 2017-12-15 | 2021-10-28 | Richter Gedeon Nyrt. | Triazolobenzazepinek |
| TW201938171A (zh) | 2017-12-15 | 2019-10-01 | 匈牙利商羅特格登公司 | 作為血管升壓素Ｖ１ａ受體拮抗劑之三環化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3818830A1 (de) * | 1988-06-03 | 1989-12-14 | Boehringer Mannheim Gmbh | Bicyclische carboxamide, verfahren zu ihrer herstellung, deren vorstufen, und diese verbindungen enthaltende arzneimittel |
| FR2686878B1 (fr) * | 1992-01-30 | 1995-06-30 | Sanofi Elf | Derives du n-sulfonyl oxo-2 indole, leur preparation, les compositions pharmaceutiques en contenant. |
| US5663431A (en) * | 1992-01-30 | 1997-09-02 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| US5686624A (en) * | 1992-01-30 | 1997-11-11 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| FR2708605A1 (fr) * | 1993-07-30 | 1995-02-10 | Sanofi Sa | Dérivés du N-sulfonylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| FR2708606B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
-
1995
- 1995-10-24 FR FR9512533A patent/FR2740136B1/fr not_active Expired - Fee Related
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1996
- 1996-10-22 TW TW085112955A patent/TW474917B/zh not_active IP Right Cessation
- 1996-10-23 AR ARP960104863A patent/AR004225A1/es active IP Right Grant
- 1996-10-23 IN IN2288DE1996 patent/IN185328B/en unknown
- 1996-10-23 MY MYPI96004404A patent/MY115864A/en unknown
- 1996-10-24 HU HU9900331A patent/HUP9900331A3/hu unknown
- 1996-10-24 RU RU98109945/04A patent/RU2167864C2/ru not_active IP Right Cessation
- 1996-10-24 US US09/051,900 patent/US5994350A/en not_active Expired - Lifetime
- 1996-10-24 DK DK96934967T patent/DK0873309T3/da active
- 1996-10-24 UA UA98042064A patent/UA59345C2/uk unknown
- 1996-10-24 AU AU73080/96A patent/AU715841B2/en not_active Ceased
- 1996-10-24 EE EE9800151A patent/EE04433B1/xx not_active IP Right Cessation
- 1996-10-24 AT AT96934967T patent/ATE229940T1/de active
- 1996-10-24 EP EP96934967A patent/EP0873309B1/fr not_active Expired - Lifetime
- 1996-10-24 TR TR1998/00719T patent/TR199800719T2/xx unknown
- 1996-10-24 BR BR9611198A patent/BR9611198A/pt not_active IP Right Cessation
- 1996-10-24 JP JP51636397A patent/JP3274471B2/ja not_active Expired - Fee Related
- 1996-10-24 NZ NZ320352A patent/NZ320352A/xx not_active IP Right Cessation
- 1996-10-24 DE DE69625517T patent/DE69625517T2/de not_active Expired - Lifetime
- 1996-10-24 SK SK490-98A patent/SK284546B6/sk not_active IP Right Cessation
- 1996-10-24 WO PCT/FR1996/001666 patent/WO1997015556A1/fr active IP Right Grant
- 1996-10-24 ES ES96934967T patent/ES2191769T3/es not_active Expired - Lifetime
- 1996-10-24 CZ CZ19981267A patent/CZ295585B6/cs not_active IP Right Cessation
- 1996-10-24 IL IL12400296A patent/IL124002A/en not_active IP Right Cessation
- 1996-10-24 ZA ZA968945A patent/ZA968945B/xx unknown
- 1996-10-24 PL PL96326555A patent/PL187093B1/pl not_active IP Right Cessation
- 1996-10-24 KR KR1019980702996A patent/KR100298925B1/ko not_active Expired - Fee Related
- 1996-10-24 CN CN96198579A patent/CN1106384C/zh not_active Expired - Fee Related
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1998
- 1998-04-14 IS IS4714A patent/IS1949B/is unknown
- 1998-04-23 NO NO19981817A patent/NO310974B1/no not_active IP Right Cessation
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1999
- 1999-10-12 US US09/417,190 patent/US6046341A/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20121024 |