DE69911235D1 - Neuartige ester abgeleitet von substituierten phenyl-cyclohexyl-verbindungen - Google Patents
Neuartige ester abgeleitet von substituierten phenyl-cyclohexyl-verbindungenInfo
- Publication number
- DE69911235D1 DE69911235D1 DE69911235T DE69911235T DE69911235D1 DE 69911235 D1 DE69911235 D1 DE 69911235D1 DE 69911235 T DE69911235 T DE 69911235T DE 69911235 T DE69911235 T DE 69911235T DE 69911235 D1 DE69911235 D1 DE 69911235D1
- Authority
- DE
- Germany
- Prior art keywords
- innovative
- substituted phenyl
- esters derived
- cyclohexyl compounds
- cyclohexyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C219/28—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C219/28—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C219/30—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009802329A ES2141688B1 (es) | 1998-11-06 | 1998-11-06 | Nuevos esteres derivados de compuestos fenil-ciclohexil sustituidos. |
| ES9802329 | 1998-11-06 | ||
| PCT/ES1999/000352 WO2000027799A1 (es) | 1998-11-06 | 1999-11-04 | Nuevos esteres derivados de compuestos fenil-ciclohexil sustituidos |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69911235D1 true DE69911235D1 (de) | 2003-10-16 |
| DE69911235T2 DE69911235T2 (de) | 2004-07-01 |
Family
ID=8305698
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69914229T Expired - Fee Related DE69914229T2 (de) | 1998-11-06 | 1999-11-04 | Neuartige Ester abgeleitet von substituierten Phenyl-Zyklohexyl-Verbindungen |
| DE69911235T Expired - Fee Related DE69911235T2 (de) | 1998-11-06 | 1999-11-04 | Neuartige ester abgeleitet von substituierten phenyl-cyclohexyl-verbindungen |
| DE69914231T Expired - Fee Related DE69914231T2 (de) | 1998-11-06 | 1999-11-04 | Neuartige Ester abgeleitet von substituierten Phenyl-Zyklohexyl-Verbindungen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69914229T Expired - Fee Related DE69914229T2 (de) | 1998-11-06 | 1999-11-04 | Neuartige Ester abgeleitet von substituierten Phenyl-Zyklohexyl-Verbindungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69914231T Expired - Fee Related DE69914231T2 (de) | 1998-11-06 | 1999-11-04 | Neuartige Ester abgeleitet von substituierten Phenyl-Zyklohexyl-Verbindungen |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US6455585B1 (de) |
| EP (3) | EP1219594B1 (de) |
| JP (1) | JP2002529442A (de) |
| KR (1) | KR100453613B1 (de) |
| CN (1) | CN1176902C (de) |
| AP (1) | AP1222A (de) |
| AT (3) | ATE257837T1 (de) |
| AU (1) | AU755681B2 (de) |
| BG (1) | BG105556A (de) |
| BR (1) | BR9915727A (de) |
| CA (1) | CA2349245A1 (de) |
| CR (1) | CR6368A (de) |
| CU (1) | CU23006A3 (de) |
| CZ (1) | CZ20011500A3 (de) |
| DE (3) | DE69914229T2 (de) |
| DK (3) | DK1219594T3 (de) |
| EA (1) | EA003742B1 (de) |
| EE (1) | EE200100246A (de) |
| ES (4) | ES2141688B1 (de) |
| GE (1) | GEP20033116B (de) |
| HR (1) | HRP20010412B1 (de) |
| HU (1) | HUP0104218A3 (de) |
| ID (1) | ID29017A (de) |
| IL (1) | IL142592A0 (de) |
| IS (1) | IS5934A (de) |
| MA (1) | MA26765A1 (de) |
| MX (1) | MXPA01004432A (de) |
| NO (1) | NO20012234D0 (de) |
| NZ (1) | NZ511739A (de) |
| OA (1) | OA11672A (de) |
| PL (1) | PL347492A1 (de) |
| PT (3) | PT1127871E (de) |
| SI (3) | SI1127871T1 (de) |
| SK (1) | SK284068B6 (de) |
| TR (3) | TR200200416T2 (de) |
| UA (1) | UA59477C2 (de) |
| WO (1) | WO2000027799A1 (de) |
| YU (1) | YU29601A (de) |
| ZA (1) | ZA200104026B (de) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2160534B1 (es) * | 1999-12-30 | 2002-04-16 | Vita Invest Sa | Nuevos esteres derivados de (rr,ss)-2-hidroxibenzoato de 3-(2-dimetilaminometil-1-hidroxiciclohexil) fenilo. |
| DE10049483A1 (de) * | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte 1-Aminobutan-3-ol-Derivate |
| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| AU2003264311A1 (en) * | 2002-08-28 | 2004-04-08 | Jin Wang | Oral formulations of ibuprofen and tramadol, methods and preparation thereof |
| EP3662904A1 (de) | 2002-11-22 | 2020-06-10 | Grünenthal GmbH | (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol zur behandlung von entzündungsschmerz |
| US20040248979A1 (en) * | 2003-06-03 | 2004-12-09 | Dynogen Pharmaceuticals, Inc. | Method of treating lower urinary tract disorders |
| DE102005005446A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| DE102004032051A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102004034619A1 (de) * | 2004-07-16 | 2006-02-23 | Grünenthal GmbH | Substituierte Aminoverbindungen als 5-HT/NA Uptakehemmer |
| DE102005005449A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| DE102007011485A1 (de) | 2007-03-07 | 2008-09-11 | Grünenthal GmbH | Darreichungsform mit erschwertem Missbrauch |
| TWI454288B (zh) | 2008-01-25 | 2014-10-01 | Gruenenthal Chemie | 藥物劑型 |
| CA2723438C (en) | 2008-05-09 | 2016-10-11 | Gruenenthal Gmbh | Process for the preparation of an intermediate powder formulation and a final solid dosage form under usage of a spray congealing step |
| ES2534908T3 (es) | 2009-07-22 | 2015-04-30 | Grünenthal GmbH | Forma de dosificación de liberación controlada extruida por fusión en caliente |
| BR112012001244A2 (pt) | 2009-07-22 | 2020-12-08 | Gruünenthal Gmbh | Forma de dosagem resitente à adulteração, seu processo de produção, e embalagem contendo tal forma |
| EP2383255A1 (de) * | 2010-04-28 | 2011-11-02 | Lacer, S.A. | Neue Verbindungen, deren Synthese und Verwendung bei der Schmerzbehandlung |
| JP5925779B2 (ja) | 2010-09-02 | 2016-05-25 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 無機塩を含む不正使用抵抗性剤形 |
| MX2013002293A (es) | 2010-09-02 | 2013-05-09 | Gruenenthal Gmbh | Forma de dosificacion resistente a alteracion que comprende un polimero anionico. |
| WO2012100423A1 (en) * | 2011-01-27 | 2012-08-02 | Eli Lilly And Company | Analgesic compounds, methods, and formulations |
| EP2530072A1 (de) | 2011-06-03 | 2012-12-05 | Lacer, S.A. | Neue Verbindungen, deren Synthese und Verwendung bei der Schmerzbehandlung |
| US10702485B2 (en) | 2011-07-09 | 2020-07-07 | Syntrix Biosystems Inc. | Compositions and methods for overcoming resistance to tramadol |
| JP6063462B2 (ja) | 2011-07-29 | 2017-01-18 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 即時薬剤放出を提供するタンパーレジスタント錠剤 |
| JP2014524925A (ja) | 2011-07-29 | 2014-09-25 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 即時薬剤放出を提供するタンパーレジスタント錠剤 |
| MX356421B (es) | 2012-02-28 | 2018-05-29 | Gruenenthal Gmbh | Forma de dosificacion resistente a la manipulacion indebida que comprende un compuesto farmacologicamente activo y un polimero anionico. |
| MX362357B (es) | 2012-04-18 | 2019-01-14 | Gruenenthal Gmbh | Forma de dosificacion farmaceutica resistente a la adulteracion y resistente a la liberacion inmediata de la dosis. |
| WO2013168005A2 (en) * | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of restless leg syndrome and fibromyalgia |
| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| MX2015016254A (es) | 2013-05-29 | 2016-04-20 | Gruenenthal Gmbh | Forma de dosificacion resistente al uso indebido con perfil de liberacion bimodal. |
| BR112015026549A2 (pt) | 2013-05-29 | 2017-07-25 | Gruenenthal Gmbh | forma de dosagem à prova de violação contendo uma ou mais partículas |
| CN105682643B (zh) | 2013-07-12 | 2019-12-13 | 格吕伦塔尔有限公司 | 含有乙烯-醋酸乙烯酯聚合物的防篡改剂型 |
| CA2931553C (en) | 2013-11-26 | 2022-01-18 | Grunenthal Gmbh | Preparation of a powdery pharmaceutical composition by means of cryo-milling |
| CA2947786A1 (en) | 2014-05-12 | 2015-11-19 | Grunenthal Gmbh | Tamper resistant immediate release capsule formulation comprising tapentadol |
| CA2983642A1 (en) | 2015-04-24 | 2016-10-27 | Grunenthal Gmbh | Tamper-resistant dosage form with immediate release and resistance against solvent extraction |
| EP3346991A1 (de) | 2015-09-10 | 2018-07-18 | Grünenthal GmbH | Schutz vor oraler überdosierung mit missbrauchssicheren formulierungen mit sofortiger freisetzung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1199764B (de) * | 1963-04-02 | 1965-09-02 | Gruenenthal Chemie | Verfahren zur Herstellung von basisch substituierten Phenolaethern |
| US3652589A (en) * | 1967-07-27 | 1972-03-28 | Gruenenthal Chemie | 1-(m-substituted phenyl)-2-aminomethyl cyclohexanols |
| DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| DE19609847A1 (de) * | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
-
1998
- 1998-11-06 ES ES009802329A patent/ES2141688B1/es not_active Expired - Fee Related
-
1999
- 1999-04-11 UA UA2001063799A patent/UA59477C2/uk unknown
- 1999-11-04 PT PT99953994T patent/PT1127871E/pt unknown
- 1999-11-04 YU YU29601A patent/YU29601A/sh unknown
- 1999-11-04 DK DK02075838T patent/DK1219594T3/da active
- 1999-11-04 CN CNB998129259A patent/CN1176902C/zh not_active Expired - Fee Related
- 1999-11-04 AP APAP/P/2001/002161A patent/AP1222A/en active
- 1999-11-04 BR BR9915727-6A patent/BR9915727A/pt not_active IP Right Cessation
- 1999-11-04 EP EP02075838A patent/EP1219594B1/de not_active Expired - Lifetime
- 1999-11-04 SI SI9930450T patent/SI1127871T1/xx unknown
- 1999-11-04 DK DK02075837T patent/DK1219623T3/da active
- 1999-11-04 GE GEAP19995930A patent/GEP20033116B/en unknown
- 1999-11-04 TR TR2002/00416T patent/TR200200416T2/xx unknown
- 1999-11-04 PT PT02075837T patent/PT1219623E/pt unknown
- 1999-11-04 EP EP02075837A patent/EP1219623B1/de not_active Expired - Lifetime
- 1999-11-04 DE DE69914229T patent/DE69914229T2/de not_active Expired - Fee Related
- 1999-11-04 EP EP99953994A patent/EP1127871B1/de not_active Expired - Lifetime
- 1999-11-04 WO PCT/ES1999/000352 patent/WO2000027799A1/es not_active Application Discontinuation
- 1999-11-04 TR TR2002/00415T patent/TR200200415T2/xx unknown
- 1999-11-04 ES ES02075837T patent/ES2213731T3/es not_active Expired - Lifetime
- 1999-11-04 AT AT02075837T patent/ATE257837T1/de not_active IP Right Cessation
- 1999-11-04 DE DE69911235T patent/DE69911235T2/de not_active Expired - Fee Related
- 1999-11-04 SI SI9930540T patent/SI1219594T1/xx unknown
- 1999-11-04 CA CA002349245A patent/CA2349245A1/en not_active Abandoned
- 1999-11-04 OA OA1200100111A patent/OA11672A/en unknown
- 1999-11-04 KR KR10-2001-7005667A patent/KR100453613B1/ko not_active IP Right Cessation
- 1999-11-04 ID IDW00200101215A patent/ID29017A/id unknown
- 1999-11-04 CZ CZ20011500A patent/CZ20011500A3/cs unknown
- 1999-11-04 US US09/831,177 patent/US6455585B1/en not_active Expired - Fee Related
- 1999-11-04 TR TR2001/01160T patent/TR200101160T2/xx unknown
- 1999-11-04 HU HU0104218A patent/HUP0104218A3/hu unknown
- 1999-11-04 AU AU10473/00A patent/AU755681B2/en not_active Ceased
- 1999-11-04 EE EEP200100246A patent/EE200100246A/xx unknown
- 1999-11-04 SI SI9930541T patent/SI1219623T1/xx unknown
- 1999-11-04 ES ES02075838T patent/ES2213732T3/es not_active Expired - Lifetime
- 1999-11-04 EA EA200100476A patent/EA003742B1/ru not_active IP Right Cessation
- 1999-11-04 MX MXPA01004432A patent/MXPA01004432A/es unknown
- 1999-11-04 PL PL99347492A patent/PL347492A1/xx unknown
- 1999-11-04 IL IL14259299A patent/IL142592A0/xx unknown
- 1999-11-04 JP JP2000580979A patent/JP2002529442A/ja active Pending
- 1999-11-04 SK SK584-2001A patent/SK284068B6/sk unknown
- 1999-11-04 DK DK99953994T patent/DK1127871T3/da active
- 1999-11-04 PT PT02075838T patent/PT1219594E/pt unknown
- 1999-11-04 ES ES99953994T patent/ES2207298T3/es not_active Expired - Lifetime
- 1999-11-04 NZ NZ511739A patent/NZ511739A/xx unknown
- 1999-11-04 AT AT99953994T patent/ATE249418T1/de not_active IP Right Cessation
- 1999-11-04 AT AT02075838T patent/ATE257817T1/de not_active IP Right Cessation
- 1999-11-04 DE DE69914231T patent/DE69914231T2/de not_active Expired - Fee Related
-
2001
- 2001-05-03 IS IS5934A patent/IS5934A/is unknown
- 2001-05-04 NO NO20012234A patent/NO20012234D0/no unknown
- 2001-05-07 CU CU2001010920010109A patent/CU23006A3/es unknown
- 2001-05-16 CR CR6368A patent/CR6368A/es not_active Application Discontinuation
- 2001-05-17 ZA ZA200104026A patent/ZA200104026B/en unknown
- 2001-05-23 MA MA26211A patent/MA26765A1/fr unknown
- 2001-05-29 HR HR20010412A patent/HRP20010412B1/xx not_active IP Right Cessation
- 2001-06-01 BG BG105556A patent/BG105556A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |