ATA474881A - Verfahren zur herstellung von neuen benzoheterozyklischen verbindungen - Google Patents

Verfahren zur herstellung von neuen benzoheterozyklischen verbindungen

Info

Publication number
ATA474881A
ATA474881A AT0474881A AT474881A ATA474881A AT A474881 A ATA474881 A AT A474881A AT 0474881 A AT0474881 A AT 0474881A AT 474881 A AT474881 A AT 474881A AT A474881 A ATA474881 A AT A474881A
Authority
AT
Austria
Prior art keywords
producing new
benzoheterocyclic compounds
benzoheterocyclic
compounds
producing
Prior art date
Application number
AT0474881A
Other languages
English (en)
Other versions
AT395150B (de
Inventor
Hiroshi Ishikawa
Testuyuki Uno
Masanobu Kano
Kazuyuki Nakagawa
Original Assignee
Otsuka Pharma Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP55158652A external-priority patent/JPS5781486A/ja
Priority claimed from JP56063170A external-priority patent/JPS57176987A/ja
Application filed by Otsuka Pharma Co Ltd filed Critical Otsuka Pharma Co Ltd
Priority to AT2887/89A priority Critical patent/AT393383B/de
Publication of ATA474881A publication Critical patent/ATA474881A/de
Application granted granted Critical
Publication of AT395150B publication Critical patent/AT395150B/de

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
AT0474881A 1980-11-10 1981-11-05 Verfahren zur herstellung von neuen benzoheterozyklischen verbindungen AT395150B (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT2887/89A AT393383B (de) 1980-11-10 1989-12-20 Verfahren zur herstellung von neuen benzoheterozyklischen verbindungen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP55158652A JPS5781486A (en) 1980-11-10 1980-11-10 Benzo(ij)quinolidine-2-carboxylic acid derivative
JP56063170A JPS57176987A (en) 1981-04-24 1981-04-24 Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative

Publications (2)

Publication Number Publication Date
ATA474881A true ATA474881A (de) 1992-02-15
AT395150B AT395150B (de) 1992-09-25

Family

ID=26404260

Family Applications (2)

Application Number Title Priority Date Filing Date
AT0474881A AT395150B (de) 1980-11-10 1981-11-05 Verfahren zur herstellung von neuen benzoheterozyklischen verbindungen
AT2887/89A AT393383B (de) 1980-11-10 1989-12-20 Verfahren zur herstellung von neuen benzoheterozyklischen verbindungen

Family Applications After (1)

Application Number Title Priority Date Filing Date
AT2887/89A AT393383B (de) 1980-11-10 1989-12-20 Verfahren zur herstellung von neuen benzoheterozyklischen verbindungen

Country Status (19)

Country Link
US (2) US4399134A (de)
KR (1) KR880001625B1 (de)
AT (2) AT395150B (de)
AU (1) AU546358B2 (de)
CA (1) CA1179341A (de)
CH (1) CH648845A5 (de)
DE (2) DE10075035I2 (de)
DK (1) DK160940C (de)
ES (2) ES8301981A1 (de)
FI (1) FI71141C (de)
FR (1) FR2493849A1 (de)
GB (1) GB2086905B (de)
IT (1) IT1171646B (de)
NL (1) NL193457C (de)
NO (1) NO156828C (de)
PH (1) PH16685A (de)
PT (1) PT73957B (de)
SE (1) SE448542B (de)
SU (2) SU1366055A3 (de)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO156828C (no) * 1980-11-10 1987-12-02 Otsuka Pharma Co Ltd Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser.
US4380543A (en) * 1981-11-06 1983-04-19 Riker Laboratories, Inc. Antimicrobial 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acids
PH22140A (en) * 1982-06-29 1988-06-01 Daiichi Seiyaku Co Tricyclic compounds
US4443447A (en) * 1982-10-25 1984-04-17 Riker Laboratories, Inc. Phenyl-substituted tricyclic antibacterial agents
JPS5978189A (ja) * 1982-10-26 1984-05-04 Otsuka Pharmaceut Co Ltd ピロロ〔３，２，１−ｉｊ〕キノリン−５−カルボン酸誘導体
US4472406A (en) * 1982-11-12 1984-09-18 Riker Laboratories, Inc. Antimicrobial 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo [ij]quinolizine-2-carboxylic acids and derivatives
JPS59137482A (ja) * 1983-01-26 1984-08-07 Otsuka Pharmaceut Co Ltd ピロロ〔３，２，１，−ｉｊ〕キノリン−５−カルボン酸誘導体
JPS59155381A (ja) * 1983-02-22 1984-09-04 Kyorin Pharmaceut Co Ltd ベンゾキノリジンカルボン酸誘導体及びその製造法
US4473568A (en) * 1983-03-01 1984-09-25 Warner Lambert Company Antibacterial thiazolidine or thiomorpholine substituted quinolines
US4472407A (en) * 1983-03-17 1984-09-18 Riker Laboratories, Inc. Antimicrobial 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo[ij]qu
US4562195A (en) * 1984-02-02 1985-12-31 Warner-Lambert Company Reversing amnesia with saturated tricyclic nitrogen-containing diones
US4571396A (en) * 1984-04-16 1986-02-18 Warner-Lambert Company Antibacterial agents
US4550103A (en) * 1984-07-20 1985-10-29 Warner-Lambert Company Antibacterial 1-oxo-benzoquinolizine-2-carboxylic acids
CA1253154A (en) * 1985-05-24 1989-04-25 Atsushi Takagi Benzo¬ij|quinolizine-2-carboxylic acid derivatives
US4940710A (en) * 1986-01-17 1990-07-10 American Cyanamid Company 7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids
US5210193A (en) * 1986-01-17 1993-05-11 American Cyanamid Company Piperazine derivatives
US4948894A (en) * 1989-02-21 1990-08-14 American Cyanamid Company 8-fluoro and 7, 8, 10-trifluoro-9-(substituted)-6-oxo-6H-benzo-(C)quinolizine-5-carboxylic acids
KR900014383A (ko) * 1989-03-29 1990-10-23 원본미기재 피롤로퀴놀린 유도체, 이의 제조방법 및 이를 사용한 항균제
US6034100A (en) * 1993-03-10 2000-03-07 Otsuka Pharmaceutical Co., Ltd. Method for inhibiting cytokine secretion
EP0688218B1 (de) * 1993-03-10 1999-11-17 Otsuka Pharmaceutical Co., Ltd. Interleukin-1 inhibitor
WO1997044034A1 (fr) * 1996-05-20 1997-11-27 Otsuka Pharmaceutical Co., Ltd. Remede pour le traitement de l'acne rosacee
DE19718065A1 (de) * 1997-04-29 1998-11-05 Henkel Kgaa Reinigungsmittel für nachvernetzende Polyurethan-Hotmelts
US6750224B1 (en) 1999-05-07 2004-06-15 Wockhardt Limited Antibacterial optically pure benzoquinolizine carboxylic acids, processes, compositions and methods of treatment
EP1175217B8 (de) 1999-05-07 2009-03-18 Wockhardt Limited (s)-benzochinolizincarbonsäuren und ihre verwendung als antibakterielle mittel
US6514986B2 (en) 2000-11-22 2003-02-04 Wockhardt Limited Chiral fluoroquinolone arginine salt forms
DE19962470A1 (de) * 1999-12-22 2001-07-12 Schulz Hans Herrmann Verwendung von Chemotherapeutika
EP1311506B1 (de) * 2000-05-08 2007-11-14 Wockhardt Limited Chirale fluorochinolizinon arginine salze
US6608078B2 (en) * 2000-05-08 2003-08-19 Wockhardt Limited Antibacterial chiral 8-(substituted piperidino)-benzo [i,j] quinolizines, processes, compositions and methods of treatment
WO2001085728A2 (en) * 2000-05-08 2001-11-15 Wockhardt Limited Antibacterial chiral 8-(substituted piperidino)-benzo [i, j] quinolizines, processes, compositions and methods of treatment
US7098219B2 (en) 2000-08-01 2006-08-29 Wockhart Limited Inhibitors of cellular efflux pumps of microbes
US6878713B2 (en) * 2001-04-25 2005-04-12 Wockhardt Limited Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments
US6964966B2 (en) 2001-04-25 2005-11-15 Wockhardt Limited Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments
WO2003050107A1 (en) * 2001-12-13 2003-06-19 Wockhardt Limited New generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments
EP1918289A3 (de) 2002-05-28 2009-08-19 Wockhardt Limited Kristalline Form eines Fluorchinolon-Argininsalzes
US6664267B1 (en) * 2002-05-28 2003-12-16 Wockhardt Limited Crystalline fluoroquinolone arginine salt form
EP1589972A1 (de) * 2002-12-31 2005-11-02 Wockhardt Limited Benzochinolizin-2-carboxysäuren enthaltende zubereitungen
CA2512199A1 (en) * 2002-12-31 2004-07-15 Wockhardt Limited Compositions of benzoquinolizine carboxylic acid antibiotic drug
US7164023B2 (en) * 2003-09-04 2007-01-16 Wockhardt Limited Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate
PT1954697E (pt) * 2005-10-21 2010-05-17 Glaxo Group Ltd Compostos tricíclicos peri-condensados úteis como agentes antibacterianos
JP6240063B2 (ja) 2011-04-28 2017-11-29 ザ ブロード インスティテュート， インコーポレイテッド ヒストンデアセチラーゼ阻害剤
US9790184B2 (en) 2012-07-27 2017-10-17 The Broad Institute, Inc. Inhibitors of histone deacetylase
WO2014100438A1 (en) 2012-12-20 2014-06-26 The Broad Institute, Inc. Cycloalkenyl hydroxamic acid derivatives and their use as histone deacetylase inhibitors
TWI641372B (zh) 2013-03-15 2018-11-21 美商梅琳塔有限責任公司 使用抗生素治療超重和肥胖患者感染的方法
KR102103256B1 (ko) 2013-10-14 2020-04-23 에자이 알앤드디 매니지먼트 가부시키가이샤 선택적으로 치환된 퀴놀린 화합물
KR102365952B1 (ko) 2013-10-14 2022-02-22 에자이 알앤드디 매니지먼트 가부시키가이샤 선택적으로 치환된 퀴놀린 화합물

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE793524A (fr) * 1971-12-30 1973-06-29 Riker Laboratories Inc Acides benzoquinolizine-carboxyliques et leurs derives
US4001243A (en) * 1972-11-02 1977-01-04 Riker Laboratories, Inc. Substituted benzo(ij)quinolizine-2-carboxylic acids and derivatives thereof
US3917609A (en) * 1973-06-27 1975-11-04 Minnesota Mining & Mfg Pyrroloquinoline carboxylic acids and derivatives
US4416884A (en) * 1978-04-12 1983-11-22 Otsuka Pharmaceutical Co., Ltd. Piperazinylbenzoheterocyclic compounds
DE2953974C2 (de) * 1978-04-12 1992-06-25 Otsuka Pharmaceutical Co., Ltd., Tokio/Tokyo, Jp
JPS6019910B2 (ja) * 1979-10-11 1985-05-18 大塚製薬株式会社 ベンゾ〔ｉｊ〕キノリジン−２−カルボン酸誘導体及びその製造法
JPS5540616A (en) * 1978-09-14 1980-03-22 Otsuka Pharmaceut Co Ltd Preparation of benzo-hetero-compound
JPS5630964A (en) * 1979-08-22 1981-03-28 Kyorin Pharmaceut Co Ltd Novel substituted quinolinecarboxylic acid and its preparation
JPS55149284A (en) * 1980-05-02 1980-11-20 Otsuka Pharmaceut Co Ltd Piperazinylbenzo heterocyclic derivative
NO156828C (no) * 1980-11-10 1987-12-02 Otsuka Pharma Co Ltd Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser.
PT74145B (en) * 1980-12-18 1983-05-30 Otsuka Pharma Co Ltd Process for preparing benzoheterocyclic compounds

Also Published As

Publication number Publication date
FR2493849A1 (fr) 1982-05-14
NO156828C (no) 1987-12-02
CA1179341A (en) 1984-12-11
AT393383B (de) 1991-10-10
FI813526L (fi) 1982-05-11
ES516523A0 (es) 1983-12-01
DK495281A (da) 1982-05-11
ES8401035A1 (es) 1983-12-01
FR2493849B1 (de) 1984-12-28
NL8105075A (nl) 1982-06-01
NO156828B (no) 1987-08-24
PT73957A (en) 1981-12-01
ATA288789A (de) 1991-03-15
AU546358B2 (en) 1985-08-29
DE3144455C2 (de) 1990-10-04
KR880001625B1 (ko) 1988-09-02
DE3144455A1 (de) 1982-06-24
AT395150B (de) 1992-09-25
US4552879A (en) 1985-11-12
DE10075035I1 (de) 2001-02-22
AU7733581A (en) 1982-08-05
CH648845A5 (de) 1985-04-15
DE10075035I2 (de) 2002-03-28
KR830007643A (ko) 1983-11-04
FI71141B (fi) 1986-08-14
IT1171646B (it) 1987-06-10
US4399134A (en) 1983-08-16
DK160940C (da) 1991-10-21
SU1366055A3 (ru) 1988-01-07
SU1277896A3 (ru) 1986-12-15
ES507493A0 (es) 1983-02-01
GB2086905A (en) 1982-05-19
SE448542B (sv) 1987-03-02
PT73957B (en) 1983-04-18
NO813726L (no) 1982-05-11
DK160940B (da) 1991-05-06
NL193457C (nl) 1999-11-02
PH16685A (en) 1983-12-13
GB2086905B (en) 1984-12-05
IT8149656A0 (it) 1981-11-09
ES8301981A1 (es) 1983-02-01
NL193457B (nl) 1999-07-01
FI71141C (fi) 1986-11-24
SE8106642L (sv) 1982-06-14

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Legal Events

Date Code Title Description
ELA Expired due to lapse of time