DE60128940T2 - C-nitroso verbindungen und deren verwendung - Google Patents
C-nitroso verbindungen und deren verwendung Download PDFInfo
- Publication number
- DE60128940T2 DE60128940T2 DE60128940T DE60128940T DE60128940T2 DE 60128940 T2 DE60128940 T2 DE 60128940T2 DE 60128940 T DE60128940 T DE 60128940T DE 60128940 T DE60128940 T DE 60128940T DE 60128940 T2 DE60128940 T2 DE 60128940T2
- Authority
- DE
- Germany
- Prior art keywords
- nitroso
- group
- compounds
- atoms
- alkyl
- 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 - Lifetime
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- 150000004006 C-nitroso compounds Chemical class 0.000 title claims description 136
- 229910052799 carbon Inorganic materials 0.000 claims description 94
- -1 amino, hydroxyl Chemical group 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 52
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 28
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 21
- 150000001721 carbon Chemical group 0.000 claims description 16
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 12
- XGELWHWQKAMULX-UHFFFAOYSA-N CC(C)CC1=CC=C(C(C=O)(N=O)C(O)=O)C=C1 Chemical compound CC(C)CC1=CC=C(C(C=O)(N=O)C(O)=O)C=C1 XGELWHWQKAMULX-UHFFFAOYSA-N 0.000 claims description 10
- 235000019260 propionic acid Nutrition 0.000 claims description 10
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
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- 150000003573 thiols Chemical class 0.000 description 7
- 208000031226 Hyperlipidaemia Diseases 0.000 description 6
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 125000000468 ketone group Chemical group 0.000 description 5
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- 208000006820 Arthralgia Diseases 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Virology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US695934 | 2000-10-26 | ||
| US09/695,934 US6359182B1 (en) | 2000-10-26 | 2000-10-26 | C-nitroso compounds and use thereof |
| PCT/US2001/027734 WO2002034705A2 (en) | 2000-10-26 | 2001-09-27 | C-nitroso compounds and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60128940D1 DE60128940D1 (de) | 2007-07-26 |
| DE60128940T2 true DE60128940T2 (de) | 2008-02-21 |
Family
ID=24795034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60128940T Expired - Lifetime DE60128940T2 (de) | 2000-10-26 | 2001-09-27 | C-nitroso verbindungen und deren verwendung |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US6359182B1 (enExample) |
| EP (1) | EP1330425B1 (enExample) |
| JP (1) | JP2004512318A (enExample) |
| AU (1) | AU2001292582A1 (enExample) |
| CA (1) | CA2422787A1 (enExample) |
| DE (1) | DE60128940T2 (enExample) |
| WO (1) | WO2002034705A2 (enExample) |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040072889A1 (en) * | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
| US20040122011A1 (en) * | 1998-12-23 | 2004-06-24 | Pharmacia Corporation | Method of using a COX-2 inhibitor and a TACE inhibitors as a combination therapy |
| AU2002211222B2 (en) | 2000-10-16 | 2006-02-09 | Duke University | Therapeutic use of aerosolized S-nitrosoglutathione in cystic fibrosis |
| US6359182B1 (en) * | 2000-10-26 | 2002-03-19 | Duke University | C-nitroso compounds and use thereof |
| US7049308B2 (en) * | 2000-10-26 | 2006-05-23 | Duke University | C-nitroso compounds and use thereof |
| US6627602B2 (en) | 2001-11-13 | 2003-09-30 | Duke University | Preventing desensitization of receptors |
| JP4563679B2 (ja) * | 2001-12-06 | 2010-10-13 | デューク ユニバーシティ | 形成外科における組織弁壊死の予防 |
| US20030212138A1 (en) * | 2002-01-14 | 2003-11-13 | Pharmacia Corporation | Combinations of peroxisome proliferator-activated receptor-alpha agonists and cyclooxygenase-2 selective inhibitors and therapeutic uses therefor |
| US20030220374A1 (en) * | 2002-01-14 | 2003-11-27 | Pharmacia Corporation | Compositions and methods of treatment involving peroxisome proliferator-activated receptor-gamma agonists and cyclooxygenase-2 selective inhibitors |
| US20040147581A1 (en) * | 2002-11-18 | 2004-07-29 | Pharmacia Corporation | Method of using a Cox-2 inhibitor and a 5-HT1A receptor modulator as a combination therapy |
| WO2004050639A2 (en) * | 2002-12-03 | 2004-06-17 | Epcellon, Inc. | 5-nitroso-6-piperazinyl-pyrimidine derivatives for treating ischemia |
| PT1572173E (pt) | 2002-12-13 | 2010-05-10 | Warner Lambert Co | Ligando alfa-2-delta para tratar sintomas do tracto urinário inferior |
| WO2004062598A2 (en) * | 2003-01-13 | 2004-07-29 | Beta Pharma, Inc. | Anti-inflammatory and anti-thrombotic compounds and their compositions |
| US20040220155A1 (en) * | 2003-03-28 | 2004-11-04 | Pharmacia Corporation | Method of providing a steroid-sparing benefit with a cyclooxygenase-2 inhibitor and compositions therewith |
| WO2005009342A2 (en) * | 2003-07-16 | 2005-02-03 | Pharmacia Corporation | Method for the treatment or prevention of dermatological disorders with a cyclooxygenase-2 inhibitor alone and in combination with a dermatological treatment agent and compositions therewith |
| US20050119262A1 (en) * | 2003-08-21 | 2005-06-02 | Pharmacia Corporation | Method for preventing or treating an optic neuropathy with a cox-2 inhibitor and an intraocular pressure reducing agent |
| US20050107350A1 (en) * | 2003-08-22 | 2005-05-19 | Pharmacia Corporation | Method for the treatment or prevention of bone disorders with a cyclooxygenase-2 inhibitor alone and in combination with a bone disorder treatment agent and compositions therewith |
| US20050187278A1 (en) * | 2003-08-28 | 2005-08-25 | Pharmacia Corporation | Treatment or prevention of vascular disorders with Cox-2 inhibitors in combination with cyclic AMP-specific phosphodiesterase inhibitors |
| WO2005023189A2 (en) * | 2003-09-03 | 2005-03-17 | Pharmacia Corporation | Method of cox-2 selective inhibitor and nitric oxide-donating agent |
| EP1708718A1 (en) | 2004-01-22 | 2006-10-11 | Pfizer Limited | Triazole derivatives which inhibit vasopressin antagonistic activity |
| US7829553B2 (en) * | 2004-02-09 | 2010-11-09 | Amulet Pharmaceuticals, Inc. | Nitric oxide-releasing polymers |
| US8470417B2 (en) | 2004-04-02 | 2013-06-25 | Curwood, Inc. | Packaging inserts with myoglobin blooming agents, packages and methods for packaging |
| US8053047B2 (en) | 2004-04-02 | 2011-11-08 | Curwood, Inc. | Packaging method that causes and maintains the preferred red color of fresh meat |
| US7867531B2 (en) | 2005-04-04 | 2011-01-11 | Curwood, Inc. | Myoglobin blooming agent containing shrink films, packages and methods for packaging |
| US8741402B2 (en) | 2004-04-02 | 2014-06-03 | Curwood, Inc. | Webs with synergists that promote or preserve the desirable color of meat |
| US8110259B2 (en) | 2004-04-02 | 2012-02-07 | Curwood, Inc. | Packaging articles, films and methods that promote or preserve the desirable color of meat |
| US8029893B2 (en) | 2004-04-02 | 2011-10-04 | Curwood, Inc. | Myoglobin blooming agent, films, packages and methods for packaging |
| US8545950B2 (en) | 2004-04-02 | 2013-10-01 | Curwood, Inc. | Method for distributing a myoglobin-containing food product |
| US7067659B2 (en) * | 2004-04-23 | 2006-06-27 | Duke University | Reactive oxygen generating enzyme inhibitor with nitric oxide bioactivity and uses thereof |
| US20070225333A1 (en) * | 2004-04-28 | 2007-09-27 | Bryans Justin S | 3-Heterocyclyl-4-Phenyl-Triazole Derivatives as Inhibitors of the Vasopressin Via Receptor |
| EP2669269B1 (en) | 2005-05-27 | 2019-05-22 | The University of North Carolina At Chapel Hill | Nitric oxide-releasing particles for nitric oxide therapeutics and biomedical applications |
| WO2007067477A1 (en) * | 2005-12-06 | 2007-06-14 | Amulet Pharmaceuticals, Inc. | Nitric oxide-releasing polymers |
| US7686448B2 (en) * | 2006-06-16 | 2010-03-30 | Marie Betts-Johnson | Eyeglass frames |
| US9259535B2 (en) | 2006-06-22 | 2016-02-16 | Excelsior Medical Corporation | Antiseptic cap equipped syringe |
| US11229746B2 (en) | 2006-06-22 | 2022-01-25 | Excelsior Medical Corporation | Antiseptic cap |
| US20080025972A1 (en) * | 2006-07-26 | 2008-01-31 | Duke University | Treating sex steriod responsive disorders |
| CN102058885B (zh) | 2006-12-22 | 2013-04-10 | 瑞蔻达蒂爱尔兰有限公司 | 采用α2δ配体和NSAID的下泌尿道疾病的联合治疗 |
| WO2008130566A1 (en) * | 2007-04-20 | 2008-10-30 | Duke University | Nitroxyl ion source with second order reaction nitroxyl release |
| WO2008130567A1 (en) * | 2007-04-20 | 2008-10-30 | Duke University | Stable neutral nitric oxide source |
| LT2318006T (lt) | 2008-08-15 | 2017-01-10 | Nivalis Therapeutics, Inc. | Nauji s-nitrozoglutationo reduktazės pirolo inhibitoriai, kaip terapiniai agentai |
| US8642628B2 (en) | 2008-08-15 | 2014-02-04 | N30 Pharmaceuticals, Inc. | Pyrrole inhibitors of S-nitrosoglutathione reductase |
| US20100098733A1 (en) * | 2008-10-16 | 2010-04-22 | Novan, Inc. | Nitric oxide releasing particles for oral care applications |
| US9078992B2 (en) | 2008-10-27 | 2015-07-14 | Pursuit Vascular, Inc. | Medical device for applying antimicrobial to proximal end of catheter |
| EP2467173B8 (en) | 2009-08-21 | 2019-06-19 | Novan, Inc. | Wound dressings, methods of using the same and methods of forming the same |
| WO2011022652A1 (en) | 2009-08-21 | 2011-02-24 | Novan, Inc. | Topical gels |
| WO2011038204A1 (en) | 2009-09-25 | 2011-03-31 | N30 Pharmaceuticals, Llc | Novel dihydropyrimidin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors |
| WO2011047013A1 (en) * | 2009-10-13 | 2011-04-21 | Novan, Inc. | Nitric oxide-releasing coatings |
| WO2011075478A1 (en) | 2009-12-16 | 2011-06-23 | N30 Pharmaceuticals, Llc | Novel thiophene inhibitors of s-nitrosoglutathione reductase |
| SI2533638T1 (sl) | 2010-02-12 | 2016-05-31 | Nivalis Therapeutics, Inc. | Novi inhibitorji S-nitrozoglutation reduktaze |
| ES2550939T3 (es) | 2010-07-16 | 2015-11-13 | Nivalis Therapeutics, Inc. | Nuevos compuestos de dihidropiridin-2-(1H)-ona como inhibidores de la S-nitrosoglutatión reductasa y antagonistas del receptor de la neurocinina-3 |
| ES2553771T3 (es) | 2010-10-08 | 2015-12-11 | Nivalis Therapeutics, Inc. | Nuevos compuestos de quinolina sustituidos como inhibidores de la S-nitrosoglutatión reductasa |
| EP2468269A1 (en) | 2010-11-26 | 2012-06-27 | Universitätsklinikum Münster | Nitric oxide donors in therapy of nitric oxide deficiency-induced disturbances of cerebral microcirculation |
| US8591876B2 (en) | 2010-12-15 | 2013-11-26 | Novan, Inc. | Methods of decreasing sebum production in the skin |
| JP5990187B2 (ja) | 2010-12-16 | 2016-09-07 | ニヴァリス・セラピューティクス・インコーポレーテッド | Ｓ−ニトロソグルタチオン還元酵素阻害薬としての新規な置換二環芳香族化合物 |
| WO2012118819A2 (en) | 2011-02-28 | 2012-09-07 | Novan, Inc. | Nitric oxide-releasing s-nitrosothiol-modified silica particles and methods of making the same |
| US10166381B2 (en) | 2011-05-23 | 2019-01-01 | Excelsior Medical Corporation | Antiseptic cap |
| CA2841832C (en) | 2011-07-12 | 2019-06-04 | Icu Medical, Inc. | Device for delivery of antimicrobial agent into a trans-dermal catheter |
| WO2013132497A1 (en) | 2012-03-07 | 2013-09-12 | Advanced Inhilation Therapies (Ait) Ltd. | Inhalation of nitric oxide for treating respiratory diseases |
| AU2015252808B2 (en) | 2014-05-02 | 2019-02-21 | Excelsior Medical Corporation | Strip package for antiseptic cap |
| EP3226859B1 (en) | 2014-12-05 | 2025-03-26 | Case Western Reserve University | Akr1a1 inhibitors for use in lowering cholesterol and modulate s-nitrosylation |
| AU2016262400B2 (en) | 2015-05-08 | 2021-01-21 | Icu Medical, Inc. | Medical connectors configured to receive emitters of therapeutic agents |
| EP4548975A3 (en) | 2015-09-09 | 2025-07-23 | Beyond Air Ltd | Nitric oxide inhalation therapy for infants with bronchiolitis |
| WO2018049027A1 (en) | 2016-09-07 | 2018-03-15 | Trustees Of Tufts College | Combination therapies using immuno-dash inhibitors and pge2 antagonists |
| CA3040277C (en) | 2016-10-14 | 2025-08-12 | Icu Medical, Inc. | DISINFECTANT CAPS FOR MEDICAL FITTINGS |
| WO2018204206A2 (en) | 2017-05-01 | 2018-11-08 | Icu Medical, Inc. | Medical fluid connectors and methods for providing additives in medical fluid lines |
| EP3765123B1 (en) | 2018-03-16 | 2026-07-15 | ICU Medical, Inc. | Sanitizing caps for medical connectors |
| US11541221B2 (en) | 2018-11-07 | 2023-01-03 | Icu Medical, Inc. | Tubing set with antimicrobial properties |
| US11541220B2 (en) | 2018-11-07 | 2023-01-03 | Icu Medical, Inc. | Needleless connector with antimicrobial properties |
| US11534595B2 (en) | 2018-11-07 | 2022-12-27 | Icu Medical, Inc. | Device for delivering an antimicrobial composition into an infusion device |
| US11517732B2 (en) | 2018-11-07 | 2022-12-06 | Icu Medical, Inc. | Syringe with antimicrobial properties |
| US11400195B2 (en) | 2018-11-07 | 2022-08-02 | Icu Medical, Inc. | Peritoneal dialysis transfer set with antimicrobial properties |
| EP3883638A1 (en) | 2018-11-21 | 2021-09-29 | ICU Medical, Inc. | Antimicrobial device comprising a cap with ring and insert |
| CN110396086B (zh) * | 2019-04-23 | 2023-03-24 | 天津国际生物医药联合研究院 | No供体类化合物、组合物、制备方法和及其应用 |
| JP7888563B2 (ja) | 2020-12-07 | 2026-07-13 | アイシーユー・メディカル・インコーポレーテッド | 医療用コネクタのためのキャップシステム、キャップと共に使用されるベース要素、及びベース要素上にキャップを保持するための方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9423868D0 (en) * | 1994-11-25 | 1995-01-11 | Wellcome Found | Compounds for use in medicine |
| GB9424694D0 (en) * | 1994-12-07 | 1995-02-01 | Wellcome Found | Compounds for use in medicine |
| EP1126838A4 (en) * | 1998-10-30 | 2005-02-16 | Nitromed Inc | NITROSIS AND NITROSYAL NON-STEROID ANTI-INFLAMMATORY COMPOUNDS, COMPOSITIONS AND METHODS OF USE |
| US6231894B1 (en) | 1999-10-21 | 2001-05-15 | Duke University | Treatments based on discovery that nitric oxide synthase is a paraquat diaphorase |
| US7049308B2 (en) * | 2000-10-26 | 2006-05-23 | Duke University | C-nitroso compounds and use thereof |
| US6359182B1 (en) * | 2000-10-26 | 2002-03-19 | Duke University | C-nitroso compounds and use thereof |
-
2000
- 2000-10-26 US US09/695,934 patent/US6359182B1/en not_active Expired - Fee Related
-
2001
- 2001-09-27 JP JP2002537699A patent/JP2004512318A/ja not_active Ceased
- 2001-09-27 AU AU2001292582A patent/AU2001292582A1/en not_active Abandoned
- 2001-09-27 DE DE60128940T patent/DE60128940T2/de not_active Expired - Lifetime
- 2001-09-27 EP EP01972952A patent/EP1330425B1/en not_active Expired - Lifetime
- 2001-09-27 WO PCT/US2001/027734 patent/WO2002034705A2/en not_active Ceased
- 2001-09-27 CA CA002422787A patent/CA2422787A1/en not_active Abandoned
- 2001-12-13 US US10/013,491 patent/US6538116B2/en not_active Expired - Fee Related
-
2003
- 2003-01-17 US US10/346,146 patent/US6887994B2/en not_active Expired - Fee Related
-
2005
- 2005-02-09 US US11/052,777 patent/US7030238B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1330425B1 (en) | 2007-06-13 |
| US20050203295A1 (en) | 2005-09-15 |
| US20020077506A1 (en) | 2002-06-20 |
| US6887994B2 (en) | 2005-05-03 |
| WO2002034705A2 (en) | 2002-05-02 |
| EP1330425A2 (en) | 2003-07-30 |
| DE60128940D1 (de) | 2007-07-26 |
| WO2002034705A3 (en) | 2002-07-11 |
| US6359182B1 (en) | 2002-03-19 |
| US6538116B2 (en) | 2003-03-25 |
| US20030176668A1 (en) | 2003-09-18 |
| AU2001292582A1 (en) | 2002-05-06 |
| CA2422787A1 (en) | 2002-05-02 |
| US7030238B2 (en) | 2006-04-18 |
| JP2004512318A (ja) | 2004-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |