CA2105707A1 - Substituted cyclohexane derivatives for the treatment of diseases - Google Patents

Substituted cyclohexane derivatives for the treatment of diseases

Info

Publication number
CA2105707A1
CA2105707A1 CA002105707A CA2105707A CA2105707A1 CA 2105707 A1 CA2105707 A1 CA 2105707A1 CA 002105707 A CA002105707 A CA 002105707A CA 2105707 A CA2105707 A CA 2105707A CA 2105707 A1 CA2105707 A1 CA 2105707A1
Authority
CA
Canada
Prior art keywords
glucose
alkyl
phenyl
solution
preparation
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.)
Abandoned
Application number
CA002105707A
Other languages
English (en)
French (fr)
Inventor
Horst Hemmerle
Peter Schindler
Roland Utz
Robert Rippel
Andreas Herling
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Individual
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
Application filed by Individual filed Critical Individual
Publication of CA2105707A1 publication Critical patent/CA2105707A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/383—Cycloaliphatic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4018—Esters of cycloaliphatic acids
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Diabetes (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Pulmonology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Transceivers (AREA)
  • Mobile Radio Communication Systems (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyridine Compounds (AREA)
CA002105707A 1992-09-09 1993-09-08 Substituted cyclohexane derivatives for the treatment of diseases Abandoned CA2105707A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4230156.4 1992-09-09
DE4230156 1992-09-09

Publications (1)

Publication Number Publication Date
CA2105707A1 true CA2105707A1 (en) 1994-03-10

Family

ID=6467599

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002105707A Abandoned CA2105707A1 (en) 1992-09-09 1993-09-08 Substituted cyclohexane derivatives for the treatment of diseases

Country Status (22)

Country Link
US (1) US5451573A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP0587087B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JPH06211737A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
KR (1) KR100299205B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CN (1) CN1042329C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AT (1) ATE181237T1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU662836B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA2105707A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CZ (1) CZ284995B6 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE59309649D1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DK (1) DK0587087T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ES (1) ES2135429T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FI (1) FI933902A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GR (1) GR3030953T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
HU (1) HUT64843A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IL (1) IL106935A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NO (1) NO179671C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PH (1) PH30278A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PL (1) PL300328A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
RU (1) RU2131248C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
TW (1) TW255880B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ZA (1) ZA936610B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4404848A1 (de) * 1994-02-16 1995-08-17 Hoechst Ag Substituierte Cyclohexanolester, ihre Verwendung zur Behandlung von Krankheiten und pharmazeutische Präparate
DE4408082A1 (de) * 1994-03-10 1995-09-14 Hoechst Ag Substituierte Propan-Derivate, Verfahren zu ihrer Herstellung und die Anwendung der Verbindungen zur Behandlung von Krankheiten
DE4416433A1 (de) * 1994-05-10 1995-11-16 Hoechst Ag Cyclohexan-Derivate, Verfahren zu ihrer Herstellung und die Verwendung der Verbindungen zur Behandlung von Krankheiten
AR012449A1 (es) * 1997-04-18 2000-10-18 Hoechst Marion Roussell Deutschland Gmbh Kodaistatinas a, b, c y d, proceso para su produccion, y su uso.
JP4810558B2 (ja) * 1997-08-08 2011-11-09 江崎グリコ株式会社 リン酸化糖およびその製造方法
DE19740080A1 (de) * 1997-09-12 1999-03-18 Hoechst Marion Roussel De Gmbh Neue Phthalaldehyd-Derivate, Verfahren zu deren Herstellung und deren Verwendung
EP1090136B1 (en) * 1998-06-24 2006-05-31 Sanofi-Aventis Deutschland GmbH Mumbaistatin, a process for its production and its use as a pharmaceutical
AU779352B2 (en) * 1999-10-25 2005-01-20 Sanofi-Aventis Deutschland Gmbh Aromatic di-keto derivatives, processes for their production and their use as a pharmaceutical
PE20021091A1 (es) * 2001-05-25 2003-02-04 Aventis Pharma Gmbh Derivados de fenilurea sustituidos con carbonamida y procedimiento para su preparacion
JP5226304B2 (ja) * 2004-06-03 2013-07-03 エーザイ・アール・アンド・ディー・マネジメント株式会社 ハリコンドリンｂ類似体の調製用中間体
ZA200700755B (en) * 2004-07-26 2009-05-27 Chugai Pharmaceutical Co Ltd Novel cyclohexane derivative, prodrug thereof and salt thereof, and therapeutic agent containing the same for diabetes
WO2009046308A1 (en) 2007-10-03 2009-04-09 Eisai R & D Management Co., Ltd. Intermediates and methods for the synthesis of halichondrin b analogs
MX2010010902A (es) 2008-04-04 2010-12-21 Eisai R&D Man Co Ltd Analogos de halicondrina b.
US20100112098A1 (en) * 2008-10-31 2010-05-06 Naturex, S.A. Effects of a decaffeinated green coffee extract on body weight control by regulation of glucose metabolism
MX2012008510A (es) 2010-01-26 2012-11-21 Eisai R&D Man Co Ltd Derivados de furo [3, 2-b] pirano utiles en la sintesis de analogos de halicondrina b.
WO2015066729A1 (en) 2013-11-04 2015-05-07 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin b
EP3505520A1 (en) 2013-12-06 2019-07-03 Eisai R&D Management Co., Ltd. Methods useful in the synthesis of halichondrin b analogs
MX392296B (es) 2015-05-07 2025-03-24 Eisai R&D Man Co Ltd Reacciones de macrociclizacion e intermediarios y otros fragmentos utiles en la sintesis de macrolidos de halicondrina.
MX377663B (es) 2016-02-12 2025-03-11 Eisai R&D Man Co Ltd Intermediarios en la sintesis de eribulina y metodos de sintesis relacionados.
JP7068204B2 (ja) 2016-06-30 2022-05-16 エーザイ・アール・アンド・ディー・マネジメント株式会社 ハリコンドリンマクロライドおよびその類縁体の合成に有用なプリンス反応および中間体
US11542269B2 (en) 2018-01-03 2023-01-03 Eisai R&D Management Co., Ltd. Prins reaction and compounds useful in the synthesis of halichondrin macrolides and analogs thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60192555A (ja) * 1984-03-13 1985-10-01 Osaka Chem Lab 抗アレルギ−食品
JPS60243016A (ja) * 1984-05-17 1985-12-03 Tsumura Juntendo Inc 抗インフルエンザウイルス剤
EP0464858A1 (en) * 1984-05-23 1992-01-08 Green Cross Corporation A lipoxygenase inhibitor
DE3603576A1 (de) * 1986-02-06 1987-08-13 Code Kaffee Handel Verwendung von gerbstoffen und/oder chlorogensaeure sowie nahrungs-, genuss- und/oder arzneimittel mit gerbstoff- und/oder chlorogensaeurezusatz

Also Published As

Publication number Publication date
IL106935A0 (en) 1993-12-28
AU662836B2 (en) 1995-09-14
FI933902A0 (fi) 1993-09-07
ZA936610B (en) 1994-03-28
HU9302527D0 (en) 1993-11-29
CZ284995B6 (cs) 1999-04-14
KR940006580A (ko) 1994-04-25
NO179671C (no) 1996-11-27
KR100299205B1 (ko) 2001-11-22
PL300328A1 (en) 1994-03-21
FI933902L (fi) 1994-03-10
NO933201L (no) 1994-03-10
NO933201D0 (no) 1993-09-08
HK1011934A1 (en) 1999-07-23
RU2131248C1 (ru) 1999-06-10
GR3030953T3 (en) 1999-11-30
FI933902A7 (fi) 1994-03-10
PH30278A (en) 1997-02-20
EP0587087B1 (de) 1999-06-16
ES2135429T3 (es) 1999-11-01
CZ186793A3 (en) 1994-03-16
JPH06211737A (ja) 1994-08-02
TW255880B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1995-09-01
EP0587087A1 (de) 1994-03-16
CN1086806A (zh) 1994-05-18
NO179671B (no) 1996-08-19
IL106935A (en) 1997-07-13
CN1042329C (zh) 1999-03-03
DE59309649D1 (de) 1999-07-22
DK0587087T3 (da) 1999-12-06
AU4617093A (en) 1994-03-17
ATE181237T1 (de) 1999-07-15
US5451573A (en) 1995-09-19
HUT64843A (en) 1994-03-28

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Date Code Title Description
EEER Examination request
FZDE Discontinued